legal move made by the ex-president donald trump in response to the search of his private residence more than three weeks ago. it's his request for an independent arbiter, a so-called special mast tore review the documents that were seized in that search. lawyers for donald trump and lawyers for the justice department squared off in federal court before judge eileen kenan who said she will issue her statement in due course. attorneys for the ex-president claim that, quote, both sides needed to turn down the temperature in this country, and then one of trump's attorney, jim trusty was dismissive of the entire probe comparing the documents seized to a, quote, overdue library book. attorneys for the justice department revealed that the process of analyzing the documents that were seized is still under way. they argued that a special master will delay that process and an attorney for doj shut

down claims by trump's attorney that this was a case about records that belonged to trump saying that the documents were not his to have. for her part, judge kennan is at times inclined to order a review of documents into a a special master. quote, justice department attorneys repeatedly pleaded with cannon not to interrupt their ongoing criminal probe that the search warrant excused on august 8th was clearly valid and authorized to obtain evidence of three significant federal crimes. cannon said she was concerned about a couple of instances in which the investigative team had flagged potentially privileged material that was not screened out during the initial review of records. that's the team that was assigned to prevent such occurrences. >> judge cannon did say that she would unseal a more detailed list by agents at mar-a-lago

meaning that we could learn a whole lot more about that extraordinary search. while we await, it is important to put it in broader context. new york times puts it like this, while the underlying investigation has immense legal and political consequence e the issue being debated at the proceeding is a fairly procedural one. the appointment of a potential master could potentially delay the process of reviewing the trove of materials that investigators carried away from mar-a-lago on august 8th and it would be uncliekly to derail the inquiry into whether trump illegally held on to national security papers at his beachfront property or obstructed attempts by examiners to retrieve them. the justice department and the twice-impeached ex-president facing off in federal court today is where we begin with some of our favorite reporters and friends. betsy woodruff swann, national correspondent for politico and also an msnbc contributor.

henry littman is back. former deputy assistant attorney general the host of the podcast talking feds plus former cia director and now an msnbc senior national security and intelligence analyst john brennan is here and with me on set, nbc news investigative correspondent tom winter. i'll start with you in the latest reporting. i take the point and "the new york times" reporting that this isn't about whether doj can proceed. it's about at what pace they are able to proceed. >> i think that's well put. i think they've looked at the trump side has looked at the idea of a special master because it is going to take some time. you have to find someone to be that special master and find somebody who might have the proper clearances and qualifications to be that person and then they've got to receive the material and sort it out. it's easier these days than pulling out file cabinets and sorting everything out on the floor and discovery and scanning documents certainly makes that easier, but having said that,

these are not the types of things that you can put on the cloud and it will take time to do it, and i think they've looked at similar investigations and this idea of a special master is not something that we've talked often about until the michael cohen investigation to the rudy giuliani investigation. so when you look at all this, you start to look at it and wonder what is the exact tactic and what is the idea here? i think if there's not that much material that is attorney-client privilege and you can certainly understand trump's reasonings for wanting to keep that out of investigators' hands and that would be proper and then you look at why they want to do it and a lot of legal experts have pointed to the fact that this would certainly slow down the process and not necessarily end it or kill it and yes, you're right, they've not attacked this point the premise for the investigation, but all of this type of litigation, if you will, all of this type of -- it's not even pretrial motions and it's before there's been anybody

charged in this case and we don't know who the subjects and targets of this investigation are and we're really in the weeds here early on with legal fights and where normally we wouldn't be at that point and we wouldn't know where this investigation would be ongoing if it wasn't this high profile of a case. >> i want to ask you, harry littman, whether it's normal for this judge to have taken this up. it was a different judge, judge reinhart, and what is this judge's jurisdiction and why is she involved in the case? >> it's one of the questions. trump filed the motion in front of her and she was the only judge there so he knew she would get it. she's technically supervises reinhart and here's what would happen in a typical case. it would go to reinhart. any disputes about attorney-client privilege would go to reinhart and without any need for a special master in the cases of michael cohen, rudy giuliani, they were lawyers so there were a lot of documents

that were potentially subject to it, but just to take slight issue with "the new york times" this may turn out to be much ado about little if all she does is appoint a special mast tore sift through the attorney-client privilege documents and there aren't that many and one thing to point out, by the way, even if they made a couple of mistakes. the consequences are so severe that someone on the team who actually sees this stuff would be disabled and it would be they couldn't serve, but -- but if and we weren't there to hear, but some of the reports would seem that she's flirting with the notion of executive privilege and that's pretty close to a disaster not just practically in terms of the ongoing review by the national security folks, but really it would up end the case because it would necessarily say he has as a former president some interest in these and if so, it undermines the whole notion that he was doing wrong when he took

them, doing wrong when he kept them, and i think that would be something the department would have to fight. if it's just about the special attorney-client stuff, i think it doesn't really matter either practically or legally. >> betsy, your take and any reporting you have on what has transpired today? >> this particular moment is very, very much peak trump in that it's the situation where the facts are totally unprecedented and the law is not always as crystal clear as we might like it to be especially when it comes to these issues of executive privilege that the judge has hinted at and that harry littman just raised a moment ago and this is a topic that doesn't get litigated or fought very often because former presidents don't want to litigate it. it does sometimes, but within the executive branch you just don't see tons and tons of

fights like this. it's not a super, super well worn path, and the facts themselves, of course, are totally generous. this has not happened. the way that the fbi is supposed to handle a former president who is dealing with materials that he removed from the white house and took to an unsecure location, that hasn't happened before. the justice department and the fiber having to put the airplane together mid-flight grappling with a wide variety and not just the concerns about the mishandling of the documents which in and of themselves are enormous and the normal standards that they are putting place for what type of relationship federal law enforcement is supposed to have with former presidents and given that this president, this former president is so unusual and has had a presidency that has been so unusual for the entire -- the totality of its time in office,

given that, the other thing that the fbi and the doj have to think about is are we actually setting precedents going forward? will there be more presidents like donald trump who want to do this kind of thing or was he so avert and outside the norm that the norms that these institutions are now setting may end up have to be harkened back to it going forward. >> such good framing on this. director brennan, i want your thoughts for not just what is happening today and what it's about and this is about an 18-month effort that gave the ex president plenty of space to reverse course and taking back things he took to lie and say i didn't mean to take them and say they were stashed with my papers and that wasn't plausible because there are no my papers and it's hard, this is about

some of the most sensitive intelligence programs that our country is a part of. we didn't run on them. some of them are programs we have reason to believe that -- that may be vital to our alliances and there are real questions and they're always worried while he was president about his agenda versus the country's. i want to show you something sue gordon said about that yesterday. >> my experience is is that the former president has his agenda and he will use whatever is at his disposal to advance that. the problem we have here is that depending on what agenda issues forth he has had at his disposal for a long period of time information that if he used that

information to advance an agenda item it could have devastating consequences to national security, but i can't think of a simpler way to say why i think that this moment is so difficult, and that's because there's no justification and knowing who he is and that he doesn't fully understand, but he may not decide to protect if he wanted to do something different. >> richard brennan, what she is very carefully articulating there is something that you grappled with as well. in the beginning it was clear that it wasn't always clear whose agenda he was pursuing, his or the nation's. >> this whole affair, nicole, is just so bizarre, but then donald trump is bizarre, and has been bizarre for the past five, six

years, ever since he entered the white house, and what we are seeing and come to understand is very, very, worrisome, and i know that national security professionals inside the government and former colleagues are shaking their heads at what damage might have been done. here is an individual who had access to this country's most sensitive national security secrets and he decided without any type of legal basis to take many documents out of the white house and bring them down to mar-a-lago in an unsecured planner and an unsecured facility and why he selected those documents and we know they're the highest classification, ts, sci and others including human control documents. why did he select these out of the thousands and thousands of documents that probably made their way into the oval office over his presidency? what was it about them that he wanted to retain them and as he

was alluding to what possible use would he make to advance any one of his agendas. and this is what i'm sure is very much worrying to do the damage risk assessments in trying to understand what might have been compromised and the sad truth is that we, quite frankly, will never know the cost. i'm sure that mar-a-lago was being targeted by other intelligence services over the last 18 to 20 months and if they were able to get individuals into that facility. and access to the rooms where the documents were and made copies of those documents. they wouldn't steal the documents and they would put them back exactly where they were, and so now the intelligence community has to try to determine if they were compromised, what damage has been done to our very sensitive technical collections systems or our human sources and other types of intelligence that this

country relies on for its national security and so therefore, it underscores not only how careless donald trump has been and how irresponsible he's been, but how malignant his presidency has been and his access to this information would have been in terms of him having access to this information. >> tom, a lot of what we know about the plausiblity with director brennan, we know from trump's own team. here's his lawyer talking about how accessible the ex-president's office is. >> i do have first-hand knowledge, as you know. i have been down there. i'm down there frequently. i have never seen that. i have never, ever seen that. that is not the way his office looks. he has guests frequently there. >> people in and out all of the time! the qanon lady from congress posted a picture of herself in the office and the government

never suggested that the photo was a live shot. it was a pile of evidence like a drug bust. you pile up the bags of cocaine. >> it is very clearly and not an exhibit, but a forensic photo, if you will. they've got a ruler out and a 2a is writ own the placard and you're looking at the dead center of the screen on top of the word special and special master. look, it's very clear that this is not a, you know, donald trump flew to new york for a deposition and he left his office like this. anybody that thought it was that just based on this photo. that's clearly not the case. back to your earlier point with respect to the documents and how they were stored i think that was the concern and that was the concern all along reading the back and forth between the justice department and what we know and what's now been reported publicly, this idea that these documents are not being properly safeguarded and as we know from the initial 15 boxes according to the justice department and the classified documents were intermingled that

came from mar-a-lago. that was the big concern and the initial big concern here that we've got a lot of documents whether they're coming back to us or not and put it aside, there are things here immediately that we need to have better safeguards over. there's no sort of, what is the mechanism or method other than the secret service presumably stopping someone from walking from one part of mar-a-lago. >> let me interrupt you. >> the secret service would only stop someone if they threaten the president. they're not vetting someone's interest in his files. >> i think that's the big concern is how many places were these files found? what were the condition where the files were found and if they are detailed with him and say the president is in another part of mar-a-lago, who is watching that part of the property. >> there are certain things that

they do do to say someone is not lying in wait and there are access to controls that they have and they just don't haver inially enough information and it appears from the justice department's court papers and filings that the stuff is stored so haphazardly that those were some of the big concerns, too. when we look at sci-type level information and say it is a profile of francis leader and that might have information that comes from people that are close to macron, that might have information from intercepts and our ability to get information from abroad. remember a number of years back they were able to get access to angela merkel's cell phone as an xafrmel and we were able to get that type of thing with macron, if so, what types of things were we able to pull off from there and that might have been advantageous to not just someone from the united states and i think that underscores the potential issue that you could have here and as we have seen and reported on, the russia

threat is because it's always come up with trump in the past, rightly or wrongly, that we have always reported on also the chinese activity in southern florida. i wrote a significant article about everything that china was up to there. undoubtedly they would have loved to get their hands on top secret, sci-level material and if any foreign leader or foreign government would get access to this and there is an affidavit that we can't see because it is redacted. >> let me ask you this, as a person in our company who has to dive into filings like these regardless of the case and the target of the investigations, what do you see when you see this months-long back and forth from nara first, to the act and when the fbi gets involved starting in april and they seem to be trying to buy some time

with congress who wants an update and the repeated attempts and the squirrelling away in a plastic folder. it's not even clear that was an appropriate package for classified material and if they handed the lies over the thorough search that meant in their view that the material had been turned over and the fact that it was still there. >> what do you see sort of building on the part of doj and law enforcement? >> first off, they've been very clear about the time line that they represent. the level of detail as far as e vents that led up to it and they have the letters from both and now that that's public, that's something we can easily digest and assess every single day. that's number one. number two, it appears that they did try to give them the benefit of the doubt. a smart lady pointed on that and this wasn't on documents and

you've got nothing to say, this was a long effort to say, you have the documents and the normal procedure is you give it back to us and there are responses and back and forths. it took a while to get to the point where there was a subpoena that was issued and even then it took a while after that for there to be a search warrant that was achieved and execute. so it does not appear that this was a rushed effort, just based on the time line and based on what i know about it and to conclude and answer, i should get back to your question and where are we going here? you said that they were in the early stages of this investigation, but they've pointed to a number of witnesses that they have. it does not appear to be an accident to me that they knew to search 45 office as they put it in their filings. so it does appear that they do have boom giving them information in terms of where things it are in the idea that they may have been newed.

i think there are a lot that they know about this, we don't go with this time will tell. this was a tough one to read because it is so unprs dented. >> so director brennan, with all that step late the and they gave the benefit of the doubt and it appears in reading these documents that 18 months ago everything was handled in a manner that would sustain this kind of scrutiny at this point. what do you make of the possible, possible scenarios for why he defied a grand jury subpoena and why he had lawyers lie about turning things over and what his motives were for hanging on to this kind of classified material? >> well, i think donald trump has always demonstrated an arrogance believing that he is not just above the regular rules

and regulations and policies, but that he can skirt them and he's clever enough to circumvent them and in many instances he has been over the years, and so therefore i think he just wanted to keep these things because he felt as though he was entitled to do that as a former president and believing that he had won the 2020 election. beyond it, what was he hoping to do with the documents with the thing that everybody is scratching their head about and not knowing what the contents are i can just have sort of nightmare scenarios about what he might want to do with them to release some information for whatever purpose, for blackmail purposes or anything else and again, he clearly was selecting documents with different code words from different timeframes. it just is very worrying in terms of why he went to such great lengths to move them out of the white house when he knew and others knew that he shouldn't have and then to conceal it and then to move them around and then to have his

lawyers and legal counsel misrepresent the facts and what was he so determined to do with them? i think that is the question. i think aside from the motive, the facts are very damning of donald trump including on the obstruction of justice front because it's clear that he knew when he was doing is wrong and coming up with these cockamamie explanning as about declassifying things when he took them out of the white house, that makes no sense whatsoever and again, i think he now has run out of the nine lives that he's had as far as skirting the law. >> former director of the cia john brennan and tom winter. thank you both so much for starting us off on this story. everyone else sticks around. when we come back just in the last few minutes a judge has handed down the longest sentence yet to one of the hundreds of people charged with attacking the u.s. capitol on january 6th. a former nypd officer facing

real prison time for attacking a d.c. cop with a flag pole and then tackling the officer to the ground. an update on that story is next. plus the doj is moving on the parallel track with another investigation into the january 6th attack on the u.s. capitol. two of donald trump's top white house lawyers expected to testify tomorrow. >> they are, of course, developments and president joe biden tonight on the urgent need to right the ship and a huge, high stakes rhyme time, and all of those stories and more as "deadline: white house" continues after a quick break. stay with us. continues after a quick break. stay with us

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>> this is breaking in the last few minutes. a judge has handed down the longest sentence by far. thomas webster is his name. let's bring in msnbc news justice reporter my colleague ryan riley with the latest. i saw your tweets about this happening today and this feels like the most severe sentence that was on the table. >> it is. actually prosecutors have been seeking 17.5 years, but he ended getting a decade behind bars and that's the longest sentence we've seen to date. the previous record was a little over seven years and two individuals who were tied to that, but what put this over the

top is the fact that a, he went to trial. b, there is violence involved and c, he lied on the stand. i think it was very clear to anyone who was watching that testimony as the jury concluded as the judge concluded, as the prosecution said. that thomas webster was making up a story about what happened that day. you can't watch that video and actually believe the story that he was trying to sell the jury and thankfully they didn't because it was just amazing to see, frankly, a former new york city police officer craft a narrative and try to sell this bs story to a jury that it was actually the other officer who was egging him on. he actually claimed that when he grabbed the officer by the face mask that he was doing that because it was a technical move becausely wanted to make sure that the officer wanted to see his hands and as if it was a stop on the highway and it was a ridiculous, ludicrous story thrown out by webster and that's why we see this record-setting

sentence in this january 6th case. >> federal prosecutors harry littman argued that nothing, quote, nothing can explain or justify mr. webster's rage. webster's one of the rioters who should have known better. no one knows better than a former cop how dangerous it was on january 6th. webster's service made his behavior, quote, particularly heinous. it's also at a human level shocking. >> all of the above. as she told judge meta who was the one who imposed the ten-year sentence basically, the doj has to make these equitable judgments with a thousand potential defendants. this guy is former law enforcement. he did go and lie on the stand and tried to sell a self-defense argument. he then at sentencing tried to say it was all post-traumatic stress disorder and he never sort of owned up to it and just

look, a picture tells a thousand words. he's got the teeth-bared rage and he's petrifying even to look at now. so for the doj that came out of the box with their longest recommendation, and you know, judge meta only gave them about two-thirds of what they were looking for, but that's still, by far, the longest hit, and i think especially being a former law enforcement officer really hit home to the court and the doj. >> betsy, this lying on the stand was dealt with this way. the justice department argued as the jury concluded that webster was clearly lying on the stand, calling his claims that the officerly attacked instigated the fight, preposterous. it would have been absolutely insane for the officer who webster assaulted who invited webster to fight him. the arguments webster and his team made could not be more at odds with his testimony. the judge says i take no pleasure in doing this when

imposing the sentence saying webster constructed an alternate truth. the cancer that was everything about donald trump's leadership has clearly included this pen chant to lying even in an institution, even in a courtroom where your future will be determined by a judge and jury. >> and what we see captured just in indisputable black and white today is the fact that lying to court, lying during a legal from seeding doesn't end well. that it's a great way to make your situation that's bad become even worse. we sort of are having an instance of instant consequences here as a report of not just of the violence and the deranged attack that this person perpetrated, but also very specifically because of the lie this he told. the other signal that this

sentence now sends which is going to be really important for the justice department broadly as it moves forward with so many of these cases that are still under way is that going to trial very much have big risks for people that are defendants in january 6th cases. doj are essentially following through on communications its had with defense attorneys saying if people decide rather than taking plea deals to go to trial, the justice department will seek lengthy sentences for those defendants. part of the reason that this is the longest sentence issued by a judge in a january 6th case is because the defendant decided to exercise his right to go to trial rather than taking a plea deal. this is a tactic broadly that is very widely used by federal prosecutors, broadly, it's something that defense attorneys often get really frustrated about and they feel it's an

abuse of the system for prosecutors to essentially twist people's arms to take plea deals and punish and exercise their rights to have a trial, but in this case the defendant clearly and totally buried himself by not just exercising his right to trial, but by subsequently lying which is the worst possible thing you can do in that setting. so it's an important moment for doj, but it's also just cautionary reminder, 800,000 that you shouldn't attack police officers violently and you shouldn't lie when you're being questioned in a legal setting like this. >> ryan, what is your -- i know you cover and report out all of these cases as they move their way through. what is the next one to come to trial. what are you watching after today? >> well, these cases are coming through every day and this will be the record for a while. i don't think that there's going

to be a sentencing in the next few weeks that can come close to this. we are stacking up these sentences as we go along and we've had a lot in the five-year range, but for a while, five years was the record for many, many, many months and that was involving a defendant from florida who was wearing a trump flag jacket when he assaulted officers with a fire exteng extinguisher and then he tried to toss it in the police line in the capitol where smfs most violence on january 6th took place. in big terms, we'll see trials coming up for oathkeepers and we will see trials coming up for the proud boys so this is going to go on for a while and i remind folks that there are hundreds more of these cases yet to come. there are hundreds of people that have been identified already by the fbi and by real sleuths and when they can actually bring those cases to fruition, nicole. >> that's amazing.

ryan, thank you so much for your reporting on this. after the break, you could probably count the names on two hands the number of people who know more about what really happened in the lead-up to the ex-president donald trump's failed coup plot, the insurrection. the former white house counsel pat cipollone and after providing public testimony to the january 6th select committee he will answer questions before a federal grand jury and what he knows and what he could reveal to them is next opinion with trelegy. with 3 medicines in 1 inhaler,... it's the only once-daily treatment for adults that takes triple action against asthma symptoms. trelegy helps make breathing easier,... improves lung function,... and lasts for 24 hours. go triple... go trelegy. because asthma has taken enough. trelegy won't replace a rescue inhaler... for sudden breathing problems. trelegy contains a medicine that increases risk of hospitalizations

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. >> there was no question in my mind and a real concern particularly after the attorney general had reached a conclusion that there wasn't sufficient election fraud to change the outcome of the election when other people kept suggesting that there was, the answer is what is it? and at some point you have to put up or shut up. that was my view. >> very interesting. today our nbc news colleague peter alexander has concerned that the man you just heard is pat cipollone, white house counsel along with pat philbin will appear surrounding the events of january 6th. these are two witnesses that saw and heard just about everything in the lead-up to donald trump's failed insurrection thanks to the january 6th committee are at

least somewhat prepared for what they might offer in that testimony outside the scope of executive privilege and it is also a big moment for the department of justice. they appear from our vantage point to play catch-up as they are in the second avenue investigation into classified documents at mar-a-lago. we are back with betsy and harry. harry, it is so interesting and obviously, the cases are separate and they originate from different potential criminal conduct and different sets of facts and these do sit at the intersection of both and i wonder what you make before a federal grand jury investigating january 6th. i'll end where i started two segments ago with the words executive privilege. this, i think is huge. we were up there and nobody except maybe meadows knows more

than cipollone and philbin. they were in for everything. they repeatedly told him what they were doing is illegal. cipollone, the reason i mentioned executive privilege, he was able to successfully parry by citing executive privilege. it was not a strong argument first biden has waived it. second, they're going after a trial in the nixon case itself says that they can go into it. so his first big question, i'm sure what they're sweating about right now, does he take the fifth amendment? bothly and philbin are professionals who want a future in the town, are solid lawyers. it would be a body blow to take the fifth. if he doesn't and he fields a question what did trump say when you told him it was unlawful, he can proffer executive privilege and the department of justice can stop the mudic, go to a

court saying no, that doesn't fly. answer the question. so unless he and philbin who is even more sort of straight up and even a greater reputation for integrity are going to take the fifth, we're going to have them face the question what exactly did trump say and that would be by a long shot the strongest evidence to date pf his potential criminality on the sixth and this is say big development. >> i want to understand your point about the fifth. they didn't take the fifth on the january 6th committee meetings. you're saying if a lawyer has advised them if they have criminal exposure. you don't take the fifth unless you, too, may incriminate yourself, right? >> they won't, but listen, he's looking at potential conspirator liability. i agree with you, they tried to walk the line, but when you work as a lawyer for donald trump as

we are also seeing in mar-a-lago could you ever be charged with having some role in a decision to go forward and of course, that would be a disaster. f the dilemma. i am just saying that if they don't, then the consequences are enormous because the questions that he didn't answer in front of the committee he should have to answer in front of the grand jury. >> yeah. i mean, harry, to be clear. i'm not saying they don't have anything to worry about. i just think -- and this is right on again and ultimately goes and spends 30 hours with robert mueller. he doesn't want anyone in law enforcement to view him as part of a conspiracy to obstruct the muller probe and ties to russia. >> yes. >> let me play some of what the justice department was to have watched very, very closely and this is cassidy hutchinson's testimony about cipollone. >> i remember pat saying to him

something to the effect of the rioters have gotten to the capitol, mark. we need to go down and see the president now, and mark looked up and said he doesn't want to do anything, pat. and pat said something to the effect of -- and very clearly said this to mark, something to the effect of, mark, something needs to be done or people will die will the blood will be on your f-ing hands. i'm going to go down there. >> it doesn't get more serious than that and this is testimony that was watched very closely by the justice department, and it has been testified before congress and not disputed that pat cipollone thought that people were going to die and the blood would be on mark meadows' hands for doing nothing. talk about him in the story as a witness. >> everything that we know about

the way that the 24 hours of january 6th played out indicates that cipollone was horrified by the violence that he saw unfolding that day. we also know from witness testimony, and to cassidy hutchinson as well, the counsel's office specifically said that the ultimate elector scheme that trump and his allies were pushing was not legally sound. that scheme, of course, played a key role in trump and john eastman and rudy giuliani really firing up, revving up the crowd that day by holding out this nonsensical hope that there might still be one way to get congress to overturn the outcome of the election. we -- according to hutchinson's testimony cipollone's view very much was that just wasn't a thing that was going to happen. it wasn't a thing that was going to work.

it wasn't lawful. she was pretty explicit about that, about the way that counsel's office felt on that particular point. i would -- look, it's always possible for people to plead the fifth in any sort of setting such as this. i would be really, really shocked if pat cipollone or patrick philbin did that on behalf of president trump particularly given that they both have already cooperated with the select committee as well and according to reporting, have also spoken to the fbi about documents that trump took to mar-a-lago in violation of the presidential records act. i don't see any sort of assertion happening on the part of either of those lawyers. the more complicated question is how issues related to executive privilege play in with the way that they do and don't field questions in the grand jury testimony. >> we also know that pat cipollone testified in those public hearings about the

federal government seizing voting machines and he said that was a terrible idea for the country. >> one more thing -- >> go ahead. >> if they have lawyers, they can seek immunity for their testimony and given their relative lack of culpability the department might well look favorably on it and then of course, there wouldn't be an issue. >> we'll watch all of this. thank you both so much for helping us navigate on what may happen tomorrow. betry woodruff swann and harry littman, thank you for being with us today. >> a democrat defeated sarah palin and flipping a house seat controlled by republicans for nearly 50 years. there was a whole lot of things and among them another test for the gop in november among voters' appetite for more of the shall we say trumpian-like candidate. she was backed by donald trump. and we'll talk about what sarah

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an answer that leads to even more answers. mayo clinic. you know where to go. a history-making result alaska's special election to feel the late don young's seat in the house. the winner, mary peltola, ten-year veteran of alaska's state legislature, will be the first woman to hold that state's at large u.s. congressional seat ever, and the first democratic candidate to -- democratic congresswoman to do so in decades. she's also the very first alaska

native elected to congress. among her opponents, one sarah palin. following her loss, sarah palin said the new ranked-choice system was a mistake for alaska in a state donald trump won by ten points in 2020. joining us now, my friend, a.b. stoddard, associate editor and columnist for real clear politics. sarah palin is sort of the one political show that i can't even bring myself to watch, but i did read about it this morning, and i wonder what you think the broader takeaways are, that palin, who, in fairness to palin, was all things trump, better and before donald trump ever was. so, if that's what they're into, she is that and then some. but the voters of alaska were not that into her. >> that's right, nicole. she certainly ushered in an era of sort of scorched earth and confrontational combat politics that the base loved.

and republicans like john mccain discovered that in 2008, and it's been a very unhappy marriage ever since between what's now only a few remaining establishment republicans and trump's republican party that really evolved from sarah palin's entrance on to the stage. what she didn't understand -- you mentioned ranked choice voting. it is a process designed to force candidates to moderate and to appeal to a broad spectrum of the electorate in order to be chosen as second and third choices, if not the voters' first choice, and so candidates are nice to each other. they talk about results and concerns of the voters. they don't just trash each other, and it's not liked by the far-right. there are not as many complaints from the far-left about this election reform but certainly someone like donald trump doesn't want state ranked choice voting because he wants the power to control primaries.

so, it did not help sarah palin, and what also didn't help her is she hasn't realized that she stepped down as governor after two years in 2009 to become a full-time political celebrity, and the voters of alaska didn't like it, and they haven't forgotten it, and she just doesn't understand, in today's republican party, where you can just be a political celebrity, that people haven't reconciled that, forgiven that. she didn't have a health problem or a family crisis. she just left to sort of go on fox news and be fabulous, and she did not make an appealing candidate because of that, which is why she was not the second choice to the other republican in the race, the second choice became mary peltola. >> do you think it portends anything nationally? >> well, nicole, we're seeing republicans struggle in these

special elections. this is the -- i believe the fifth in a sequence of them that democrats have overperformed in. the forecasters and experts like to tell us, those have been low turnout events where they are not exactly the make-up of the electorate we're going to be seeing across the country in november, and at this point, i don't think we understand which party really has the upper hand going into what has become an x factor election and not a traditional midterm. but certainly, mary peltola will have a time having to hold on to that seat and run again in november, but if the electorate is engaged and energized by things like the dobbs decision, then she might be able to hold on. >> so interesting. a.b. sticks around, and we don't want you to go anywhere either. we are still waiting for that decision from the florida federal judge on the ex-president's request for a special master. much more on that story right after a quick break. don't go anywhere. that story r after a quick break. don't go anywhere.

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♪♪ what i saw from the last two days was absolutely atrocious. these documents, joe, were in mar-a-lago, a place where you rent out croquet sets and badminton nets and golf carts. these are the nation's top secrets that could reveal intelligence sources and put people at risk in the field, patriots, who are simply trying to protect the security of our country. >> hi again, everyone, it's 5:00 in new york. you know, the place where you rent croquet sets and golf carts. it's where everybody keeps our

country's most classified top secrets, right? for over a year? still stunning to think about more than three weeks after the fbi searched trump's hotel and residence, mar-a-lago. this afternoon, development. trump's lawyers faced off in a federal courtroom against the justice department for the first time since that surge. the question before judge eileen canon, whether or not to appoint a special master to review the documents taken during the fbi's as much. donald trump's lawyers argued that a special master would help identify if any of the evidence seized on august 8th contains potential attorney-client or executive privilege issues. meanwhile, jay bratt argued that some of the trump team's requests were premature and that the bottom line is that trump had a stash of documents that don't belong to him. judge cannon did not announce the decision on the special master request, saying she would issue a written ruling at a later date but she did say she would make public a more detailed list of the items the fbi took during its search on august 8th, meaning we will

likely get a much better understanding of what classified information and documents the twice-impeached ex-president has been hoarding at his residence. it's where we begin the hour. ashra is here, former fbi special agent for counterintelligence, now a senior lecturer and assistant dean at yale's jackson school of business affair. a.b. stoddard is still with us. asha, take me through the significance of this today. and i shared some "new york times" reporting in the last hour that, at the end of the day, nothing is on the table to thwart the investigation. it's really a potential delay that's on the table today. >> that's what it sounds like, though honestly, given that some of these claims are so novel, and quite strange, they kind of upend some well held legal principles. it's really unclear where it

would go if she -- if this judge starts to open the door towards it. for example, i'll go with just sort of the government's argument, because it's actually logical. the government argued that trump doesn't have any possessory interest in these documents, he's not actually the legal custodian. he's basically, you know, the thief who's taken them. that he also doesn't have any executive privilege and that he's also delayed in filing this request. if she were to open the door to a special master, she then, essentially, upends some of these ideas, right? she suggests that he has -- he does have a possessory interest in these documents, which then sets it up as, you know, a competition between a former executive and a current executive in terms of the privilege. so, i'm not really sure where this would go, and i'm hoping that it won't be more than a small delay, if it is, but you know, we just have to see what

she says. >> asha, let me show you something sue gordon said about this question of classification and just this whole world view that the ex-president's attorneys seem to be arguing from, and it's not just the possession, that they belong to him, but it's around classification, that regardless of the ramifications for u.s. national security or that of our allies, he could wave a wand and do what he wants, and there's no evidence he did that anyway. here's sue. >> the act of declassifying is not a personal act. tfrs not an act of preference. it's not because i want to do something. it's because it serves either the national or the public interest, and it's a process that you go through that you work with experts to say, if i declassify this, what will the impact be, and can we bear it? so, it isn't something casually done, regardless of whether you have the authority to do so or not. and it isn't in order to protect yourself or to aggrandize

yourself. it's just -- it's an entirely different thing. >> they don't understand. something could be marked top secret, could be marked classified. the presidential records act, he would have said, this is declassified. it doesn't get a new marking all the time. he's left the office. it is a complete public spectacle. >> a million things wrong with what the ex-president's lawyer said, but let's focus on what sue gordon says first. she says, regardless of whether you have the authority to do so or not, it isn't in order to protect yourself. you don't declassify things because now you're in trouble for criminally taking them, keeping them, hoarding them and lying about giving them back. >> right. and i think sue is exactly right. what she's getting at is, these aren't just arbitrary labels that suddenly make something legal and not legal. the classification, you know, the different tiers, actually represent an assessment, a

substantive assessment of the level of damage that this information can do to national security. it's quite -- it's, frankly, probably not possible for a single person, particularly the president, to actually make that assessment on his own. that's why they, in the declassification process, you bring in the agencies that have equities, who really understand what the consequences and ramifications would be of disclosing this information. so, really, what, you know, this -- this claim that he declassified is basically saying, well, i made the judgment call that these don't damage national security, which is just not something that he is really in a position to do. so, even though, i guess, legally, as president, he could do it, i think what sue is saying, it wouldn't make any sense. the changing of those labels would not actually mean anything. you know, substantively speaking. >> and then i think, a.b., what sue gordon made clear here in

this hour yesterday is that the declassification is a process that is collaborative. it's not a decision that is unitary, because you got caught, literally, with your hand in the classified, most sensitive classified cookie jar. and there's no one arguing that it's anything other than that on the part of donald trump. >> this is preposterous. and the confusion and the b.s. is the point. the court filings have not said he -- his own lawyers have not said, in these filings, that he declassified anything, that anything that the department of justice is talking about has been declassified. and as sue gordon lays out, there is a massive paper trail for this process. it doesn't happen in donald trump's head. but he likes to put this crap out on truth social to confuse his followers and make them believe there's a new talking point to survive the next news day, and to give people on fox

news things to say in his defense. more process, more procedure, more jargon, more paperwork, more delays is the point. what's stunning to me, if you just take a look back, nicole, is that none of us had to know any of this. the president -- the former president revealed the search at mar-a-lago and then teed up the entire republican party to send out manic tweets on his behalf that night, attacking fbi agents, and in the days that followed. this is an unforced error, this request for a special master. now, asha is the legal mind, and she's probably right that this could get into very tricky areas, but it still managed to prompt a really embarrassing fact-filled, damning document from the department of justice, laying out why he is likely guilty of several federal crimes. so, it was a self-own, but again, it was a way to just have

another process that he could talk about and people could throw around on social media on his behalf, to people they do not believe are smart enough to understand. again, legally, i don't know where it's going, but it doesn't sound like it would do anything to really upset or delay, significantly, the investigation. this declassified b.s. is all intentional to confuse people on cable news and on facebook. it's not even in the document. his lawyers aren't pretending that he declassified anything. there's no paperwork to show that it happened. it's beyond belief that he's still putting it up on his whatever it is, truth social, today. >> so, a.b., there's some "new york times" reporting exactly to the effect of what you're talking about. "times" reporters write this, "it's as if trump, seeming not to fully grasp the potential hazards of his modest legal move, cracked open a door, allowing the justice department

to push past him and seize the initiative. the trump team got more than they bargained for, said preet bahra, long-time critic of trump, in response to a tardy special master motion, doj was given the opportunity to be expansive." >> precisely. none of us had to know about any of this. he didn't need to look so guilty. and what's so great about him and these lawyer women that go on tv for him is it's a symbiotic relationship. they want the fame, and they're willing to trash their entire legal career for his ridiculous requests that make him look more guilty, and everybody's happy, because for him, it's all about a pr move, and for them, they think that working with him and letting him incriminate himself and admit to potential crimes on truth social, day in and day out, when they're making these filings and working into the night to write them up, it's obviously fine with them, no matter how much he derails their own work.

so, this is all, again, a performance, and donald trump is a showman, and it's all about keeping himself in the news, raising money off of it, and just keep blowing a lot of b.s. to his voters. >> with extraordinary potential new risk being faced now by fbi agents and doj attorneys, my colleague, nbc news correspondent vaughn hillyard, is outside the courthouse where all of this went down today in west palm beach, florida. vaughn, what is the latest? >> reporter: i mean, this is a situation which you and a.b. were just outlining here, in which it's not clear the extent to which trump's lawyers understand which documents the department of justice has and that is why it was significant that the judge indicated here that she is looking to unseal a more detailed list of the documents that were seized on august 8th and are now in the hands of investigators. that came at the request of the trump team here, and it will be made public, but it's

interesting to note that it was the trump team that wants this to be made public, because they are seeking to have a better understanding of what one could say they're trying to defend the former president against here. because it was a trump lawyer and a custodian of his records who, on june 3rd, signed a sworn affidavit that all relevant documents had been turned over to the department of justice. it's not clear whether that signature was signed on the dotted lines with the understanding that, truly, all the documents under their belief had actually been turned over or not, but what we know from this filing is that more than double the number of classified materials have been seized by the fbi compared to the number of records willingly turned over by trump and his team on june 3rd here. we do not have a determination from the judge about whether a special master will be appointed here or not. the trump team is trying to make the case, and it's important to note they do have a new lawyer that is working on their team, a former florida solicitor general

who has deep ties to the republican party, worked on the transition team to ron desantis here, they are trying to make the case that it was nixon v. usa, limited case law is what they are contesting. it was obviously the unanimous decision of the supreme court that then-president nixon had to turn over not only tapes but material because a criminal investigation did not grant immunity from a current sitting president from turning over documents that could potentially help a criminal investigation. yet, that is where you see the defenders of the former president, including himself, make the case it's limited. you were talking about these lawyers. zelena, who is not actually working on this specific case, but she's a trump attorney who is going on national airwaves to talk about this case, she actually is representing him in the trump organization with the new york attorney general's office, but last night, she made a, you could say, maybe inadvertent admission in which she said that she had frequently been inside of trump's office

before, but also said, there's other guests that are frequently there, which would suggest that there are individuals who had been in the premises of these very documents the department of justice now has their hands on. >> and asha, it's clear that the fbi did two things. one, they tried to get back into the possession of the government these classified materials for many, many months. and two, there's a stream of evidence and information really coming in, in realtime, to the government, and it's clear from the filings that he doesn't know who they are, but they knew what they got was incomplete. they knew the material was in places other than the storage room. we know that from the filing. and they know that these things continue to be at risk, and as vaughn just said, exposed. >> yes. and you know, to the point that was just made, in terms of these admissions that are being, you know, made by his lawyers and even trump, that these documents

were outside of the storage room after they had certified that they had been turned in. and they were in high-traffic areas where they could have been compromised. trump said on truth social that he was upset about the photo, a standard documentation photo, he said, that's not how they were. they were in cartons. he's basically acknowledging that he knew they were stored in his office after they had told the department of justice that they had given them everything. i mean, he's basically confessing to obstruction of justice. and i think, nicole, the only explanation i can come up with is that they may be convinced -- and this is part of what they've tried to argue -- that trump is entitled to have these documents, that he -- that there's no way the fbi or department of justice can

actually enforce the ownership and custody part of the presidential records act, and back to the special master, it's not clear what the remedy is. if they identify, you know, if she goes down this road of saying, identifying documents that are executive privilege, under the law, as i read it, that means they would go back to the national archives, at the very least. maybe the lawyers think they're going go back to him. so, they seem to be behaving that way, at least in terms of the statements that they're making, because they -- they are not helping their own case when it comes to the potential criminal charges against them. >> asha, when you talk about sort of the chain of command of these documents and what the government knows, do you think there's an active investigation into whether they've been copied or squirrelled away or an inventory against which they're checking what they have been able to locate? >> well, in terms of the documents that they were looking for, there was quite a detailed list of the markings that they

were searching for when they executed the search warrant. so, they clearly do -- they knew they were missing certain things, and they knew exactly the particular documents they were looking for. i think one of the challenges here is, i'm not sure that they would be able to know if things have been duplicated. i mean, again, if you -- if these were in an office that was unsecure, with people coming through who could photograph them, i mean, that -- that's not something that a forensic review of the actual document would be able to reveal. and so, you know, i think this is going to be a part of the damage assessment is really saying, you know, are we going to just assume that all of these secrets are out there somewhere, somebody's holding them, and what does that mean in terms of our methods, our sources, our collection, and you know, our intelligence capabilities and how we're operating on them? >> vaughn, was there anything on the president's attorneys that

acknowledged or depicted the twice-impeached ex-president as cognizant of the national security importance and specialness of classified material? >> reporter: well, they made the comparison to this being an overdue library book. >> right. >> reporter: and those are the lawyers for donald trump. and donald trump is not one to have shown any regret up to this point, even suggested that evidence may have been planted at mar-a-lago here. but no, his attorneys did not make that case. but i think it's important to note that the office of the director of national intelligence is currently reviewing these very documents with the fbi, with the department of justice, to determine the extent to which there are potential national security threats. if, in fact, these documents had been either obtained, taken, photographed, somehow the contents of them had made their way outside of mar-a-lago, quite

frankly here, and that is where you saw the department of justice lawyers making the case that time was of the essence here and that, to delay this any longer could potentially put not only our sources but our methods of the u.s. national intelligence community at risk, and that is why they are making the case here, and i think that it's important to note, we don't know exactly what those documents pertain or were included, and i think that that is why you heard those lawyers make the case that that review needs to continue so they have an understanding of what is in these documents themselves. >> still, if you step back, just remarkable that an ex-president of the united states of america doesn't want a review of whether he wittingly or unwittingly exposed state secrets. vaughn hillyard, asha rangappa, a.b. stoddard, stay near. if anything breaks, we will rush you all back to your cameras. thank you for starting us off this hour. when we come back, we'll get a preview of president joe

biden's primetime address tonight in philadelphia as he makes the case that democracy is under threat and that the soul of the nation hangs in the balance. white house deputy chief of staff jen o'malley dylan will be our guest after a quick break. plus, we'll check in with one democratic senate candidate in a prime spot to flip a seat from red to blue, ohio's tim ryan, who is using an unconventional strategy to beat an extreme far-right maga republican, jd vance, the guy who says women should remain in violent marriages for the sake of the kids. and in her brand-new book, our nbc news colleague ali vitali tries to answer the provocative question, why have we yet to put a woman in the white house? "deadline white house" continues after a quick break. "deadline white house" continues after a quick break. to our third bark-ery. oh, i can tell business is going through the “woof”. but seriously we need a reliable way to help keep everyone connected from wherever we go. well at at&t we'll help you find the right wireless plan for you. so, you can stay connected to all your drivers

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nbc news has learned some new details about president joe biden's major primetime address tonight in philadelphia at the birthplace of american democracy. a senior biden administration official says the president will talk about the threats from maga republicans to our rights and to our freedoms while offering an optimistic vision about the other side of the aisle fighting to save them. the president will again address what he calls the continuing battle for the soul of the nation. it was a central pillar of his presidential campaign that he has revamped with new urgency ahead of this year's midterm elections. he aggressively portrays november's elections as another chance to save democracy. joining us now to talk about what to expect tonight from the president, white house deputy chief of staff, jennifer o'malley dylan. thank you so much for taking

time to talk to us. >> hey, nicole, great to be here. >> tell me about this moment for the president. he's been talking about democracy and the threats to our democracy since the democratic primary. some of his earliest messages to voters were about the soul of the nation. he gave one of the bigger speeches of his campaign on the topic, and then obviously, his transition and inauguration. he's had to deal in a very granular way with the very real threats to it. what about this moment has him turning back to those themes? >> yeah, absolutely. i mean, as you know, the president has been speaking about the battle for the soul of the nation since when he got into the campaign, and it was really a galvanizing issue for him, and i think he still believes that we are in that battle for the soul of the nation and that we're truly in an inflection point right now. and i think you'll hear from him tonight that he will be setting out the core values that he really feels in this country that are at stake right now.

things like our rights and equality, where we stand in the world, democracy itself, and i think he's going to say to the american people that we have to fight for that and that we can. i think you're going to hear from him something that's optimistic. you know, you hear him say all the time, i know you know this, that he believes there's nothing we can't do as a country when we come together and that we all as an american people have the power to fight for and maintain a strong democracy. so, i'm excited to hear from him tonight. i think you're going to hear some similar themes, but i think at a key moment where he really sees we're at an inflection point. >> jen, he was so committed to what i think are his deeply held beliefs, that across the other aisle were good people who saw the country differently than he did. he has either been convinced by what he has witnessed that that is no longer the case. what moved him from the ways he talked about republicans in the beginning of his presidency to

describing the maga republicans as semifascist? >> well, look, i think he believes, truly, and he has proven that you can work across the aisle to get things done. he has been able to do that on core issues that haven't happened in such a long time, like the gun legislation, like the burn pit legislation to take care of our veterans, the manufacturing bill that went through earlier this summer. so, you know, as he said in the state of the union, he believes that there are places that we can and we need to come together as a country. that's what he ran on, and that's what he believes. but at the same time, he really believes that there is an extreme element of the republican elected officials in this country that are putting forth what he calls, and he has termed a maga agenda. that is not what the majority of the american people support or want in this country. that sides with special interests, that is representing something that we as a country are not built for, and we need

to be clear and plain and direct about what's at stake and what that contrast is and also hopeful and optimistic about what we can do about it. >> on the other side, the maga republicans have used the big lie to push through close to 500 voter suppression laws disguised as voter integrity laws, and i think a lot of members of the -- a lot of democrats would have liked to see him fight differently -- i won't say harder, because i know he did fight hard -- but fight differently for voting rights. is that on the table to be an issue that he tries to renew or breathe life back into? >> well, i think the president has been so clear about the importance of abiding by and believing in free and fair elections. i think that's one of the clear contrasts that he's putting forth that we're seeing that extreme maga republican elected officials that aren't supporting free and fair elections. he was very clear that he was going to let no rule of congress stop moving forward and doing

all he can on voting rights, but at the same time, the votes aren't there to overturn the filibuster, so he has said he is going to fight for this. it is critical to the fabric of our democracy, it is critical to all of us being able to continue in the country that we have all built together, and so you're going to see him keep fighting for that. he's realistic, but he sees the possibility of how we can all come together and what it's going to take to make sure that at the national level but also at the local level, we're doing all we can to reinforce the strength of the democracy through fair and free elections that we saw in 2020 and are going to continue to see this election cycle. >> jen, i worked in the white house, so it was often under intense scrutiny with tough poll numbers, and i know what it feels like when that goes the other direction. can you just take us behind the scenes? is there this feeling that you've got some wind at your back with democracy rising in terms of being on voters' minds, with gas prices going down, with some of the crises of the last

12 months seeming to abate and the president able to get a message out? >> well, you, of course, know better than most what it's like to be on this side, and you know, obviously, the political discourse in this country often is very focused on poll numbers. we are focused, and the president is focused on getting the job done for the american people, and i think he came into office, he ran his campaign, being clear that we can deliver for the things that are impacting people in their everyday lives. he talks about it all the time, just having that breathing room for families. and what you have seen is our ability to get that done, and they have -- the american people have seen that the president's focusing on the issues they are most concerned about. there's still more progress to be made. you're going to continue to have the president have the opportunity to make that case. he's always talking about how important it is not just to talk about the legislation but the impact on real people, and i think what you're seeing reflecting in the numbers right now is that the american people are seeing the progress that's being made. they're hopeful.

you know, kids are going back to school. people are feeling like gas prices continue to come down every day. i think for 79 days now. they're seeing that progress. and they're also seeing a clear distinction between the president's vision and the extreme maga agenda on the other side, and i think that they're standing up on the side of the president, and we're going to continue to go tell that story. >> jen o'malley dillon, thank you for spending time with us. come back any time. we will be watching tonight. we'll have live coverage on msnbc starting at 8:00 eastern. when we come back, we'll head out on the campaign trail and check in with ohio's democratic senate candidate tim ryan. he's looking to defeat maga republican jd vance. he's decided to do it by trying to keep president joe biden at arm's length and to appeal to republicans. we'll find out how that's going and what it looks like after a quick break. s going and what it looks like after a quick break.

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want a permanent solution to homelessness? you won't get it with prop 27. it was written and funded by out-of-state corporations to permanently maximize profits, not homeless funding. 90% of the profits go to out-of-state corporations permanently. only pennies on the dollar for the homeless permanently. and with loopholes, the homeless get even less permanently. prop 27. they didn't write it for the homeless. they wrote it for themselves. online sports betting to fund real solutions to the homelessness crisis. so how will that new revenue be spent? new housing units in all 58 counties,

including: permanent supportive housing, tiny homes communities, project roomkey supportive hotel units... and intensive mental health and addiction treatment. in short, 27 means getting people off the streets and into housing. yes on 27. less than ten weeks to go before the midterm elections, president joe biden is riding a wave of positive headlines and legislative successes that have seen his popularity rise a good deal in recent days. polls show the president's approval ratings are up after the passage of the inflation reduction act and his student loan debt proposal and that has brought back interest from some swing-state democratic candidates running in midterm races who initially were wary about having the president campaign alongside them. the question now is whether the president would benefit candidates who have been vocal

about continuing to keep him at arm's length. one of those candidates who wants to do it his way is congressman tim ryan, running for the senate seat in ohio. he's running against jd vance. ryan is running as a moderate. ryan is a moderate democrat, trying to appeal to republicans there against the far-right extreme jd vance. let's bring in nbc news correspondent jesse kerr live in ashland, ohio, and my colleague, capitol hill correspondent ali vitali is here, author of "electable: why america hasn't put a woman in the white house yet." take me inside the tim ryan campaign. >> reporter: yeah, so, just because tim ryan is now okay with being seen at an event with joe biden, doesn't mean that he wants that, necessarily. i asked him about this upcoming event around the passage of c.h.i.p.s. and he said to me that, essentially, he's there, i'm there, we both support this

so that's okay. but i asked him if he wants the president campaigning with him, and he says, he does not. he'd rather stand on his own. he's trying to keep joe biden at arm's length because i think tim ryan would not be upset if people mistook him for a republican in this state. it went twice for donald trump, so this is a place that he is trying to flip back toward democrats, and he has an uphill battle here, especially in this county where we are, this county went for donald trump by more than 70 points, and we were asking tim ryan today about what he might be concerned about coming from the white house, specifically with the president's speech tonight, because tim ryan loves bragging about the fact that he has sided with donald trump in the past, that he has stood against joe biden and nancy pelosi, so here's what tim ryan said when i asked him about joe biden's speech tonight. >> do you worry when he singles out the maga sect, he's alienating too many people? >> i do think you got to be careful because there are a lot of people who voted for trump that don't think it's a good idea to storm the capitol. but they may have voted for

trump. i don't think we should pass judgment on those people, and that's -- that, i will never do, because we have a lot of those people supporting us. i mean, we've got a lot of two-time trump voters that are voting for tim ryan. >> reporter: so, tim ryan is saying, welcome one, welcome all with the exception of certain groups of people who he says are off-base, people he talked about tied to january 6th and people who were denying the results of the 2020 election stand as they are. so, that's tim ryan's perspective. his opponents, republicans, will tell you this is all a charade, that he is far more liberal, and we asked him about an issue such as abortion earlier. he doesn't shy away from discussing that, nicole, but he's not going to outright highlight that. his ads circle around things like jobs and china. so, you hear those buzzwords and you're not thinking about what you might hear from other democratic campaigns right now. so, he's happy for people to think he's just floating out there in the middle, not really tied to either party. >> ali, you know why? because he wants to win in ohio.

ohio is as red as can be, and you know who understands that better than any of us? joe biden. >> yeah. >> this is what happens. >> yeah. this is what happens, and look, it's also not unheard of for a democrat to win a senate seat in ohio. you've got sherrod brown, and in large part it was his local brand that was able to buoy him to the top of that race. congressman tim ryan was able to get re-elected in youngstown, ohio, an area that is a little bit more moderate but also one that is trumpy in nature. obviously, all of ohio, pretty red these days, but it makes sense that ryan is trying to run in that little of a middle ground. but also, that's the biden persona as well. i think that you and i both looked very closely at 2020 and the way that biden ran, despite the fact that republicans were trying to brand him as radical

and hyperprogressive, that was never really a moniker that necessarily stuck across the board, and so it's not necessarily biden's political persona, i think, that's the baggage here. it's inflation, higher prices at the gas pump, that's what he has been fighting against and it's partly why, as we see those prices coming down, we're seeing approval ratings going up and all of that at the same time as democrats in congress are grinding the gears to notch legislative wins as well. >> so, jesse, we talk about the tim ryan-biden factor. how much of this is that tim ryan sees this open door? jd vance is completely -- i say this as an ex-republican. a caricature of what jd vance thinks republicans in the trump era should sound like. this wasn't a gotcha interview. this was a friendly conversation where he said women should remain in violent marriages, it's good for the kids. he's what mitch mcconnell's talking about when he says, candidate quality is an issue. he has -- he's broke.

he's getting national money and private sector money. i mean, how much of tim ryan's decisions on the trail are driven by the opportunity jd vance gives him to get republicans to vote for him? >> reporter: well, i think we have to look, nicole, at what this summer has been. you talked about, there's big republican money coming in here to help prop up jd vance because there is that concern around his campaign. tim ryan has dominated the airwaves over the summer and pretty much has been getting no pushback or almost no pushback until the last few weeks. so, tim ryan has been able to direct the conversation much more than jd vance on the airwaves and the advertisements that people are seeing in ohio. so, i think jd vance's campaign now has to play some catch-up there. they've got support coming with fund-raising from a group that is supported by leader mcconnell in the senate, so they do have that help coming, and there's also this idea that people aren't necessarily paying attention until after labor day, but i do want to emphasize that

in an election climate when we talk about social issues, possibly weighing heavily on people, and i think abortion is one of the issues we keep thinking about a lot. when we're at this event with farmers today, believe it or not, i would say 99% of what was discussed here was farming, and i know that might sound comical to bring up, but i think that speaks to, at the end of the day, people are focused on the issues that are impacting their bottom line above the other things which politicians on both sides might want you to be talking about. >> jesse, i traveled every inch of ohio on a bus. it doesn't sound funny to me. it would sound funny if that wasn't the case. ohio is so hard fought over because they do pay a lot of attention to politics all year round, all four years, and they do care a lot about the issues you're talking about. we'll continue to bother you, jesse kirsch. when we come back, we're talking about ali's brand-new book that seeks to answer a burning question in my mind. why haven't we elected a woman yet for president? why haven't we elected a woman

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elections. the only people on this stage who have won every single election that they've been in are the women. amy and me. >> i love that moment. but we all know what happened next. democrats nominated joe biden to challenge and ultimately defeat donald trump in 2020. you probably heard the phrase, safe choice, right or wrong, that's what voters said they felt, especially when held up to the half dozen candidates who happened to be women. kamala harris became the first female vice president, but obviously, to this day, 46 of 46 american presidents have been men. we are back with my colleague, ali vitali, author of "electable: why america hasn't put a woman in the white house yet." ali, after i worked with sarah palin and her loss last night is something i want to ask you about, ann, a phenomenal political reporter wrote notes about hillary clinton's run and she reported out some of the palin campaign as well. what's remarkable to me about

your book is it updates so many of the same forces in america, not just political life, but civic life, that keep it this thing that is out of reach. tell me about the book and why you wrote it. >> i think that's what's so striking to me, nicole, is i opened the book, actually, in a conversation i was having over zoom with senator warren, where she asks me what this book is about, and i said, why we haven't had a female president yet. she says to me, yeah, i was working on that too, and i think that sets the whole tone for this conversation is in talking with secretary clinton for this book, almost all of the women who ran in 2020, carly fiorina in 2016 and as many other operatives and sources as i could talk to, all of them say this is something they have been actively working on, and it's kind of just a matter of time, but what's striking to me is that each election cycle, we feel like we're closer, that the country is more ready, and then once we start seeing candidates' names on a line and their policy positions behind them, that's when we start getting into the,

oh, there's just something about this particular woman that i just don't like. and that's something that requires media to disrupt the narratives in realtime, but it's also something that the more women we're used to seeing run, the less novel it will become, and potentially the less we will endeavor to see that. >> what is -- what is elizabeth warren's sort of theory on the role that gender played in her loss? >> well, we saw her talk about it in realtime, the day that i was standing with a hoard of reporters outside of her home in cambridge on the day that she dropped out. she said, if women don't speak to the fact that gender is a role in their race, people will say, what planet are you living on? but if you talk about it, other people will say they're whining, and i wanted to write this book because i'm a political reporter first. you and i have these conversations all the time about the hard politics that impact these candidates, and certainly, gender's not the only reason that we haven't had president

clinton or president warren of president klobuchar, but the unquantifiable piece of their runs is, where do you give the benefit of the doubt? the entire premise of electability is really the question of, yes, it's fair to want a candidate who can win bus yes, we want owe candidate who can win, but nobody knows until the night voter cast their votes. it comes down to, who do you give the benefit of potential, the benefit of the doubt? despite the women on the stage who won all their races, the person who had run for president two times prior to 2020 and never had any electoral wins in a prior show for it was still seen as the safest choice. >> vice president kamala harris is sort of living with these wins pressing against her as she goes about doing her job. what did you report out about the special scrutiny she faces? >> i think that first and

foremost, we should be scrutinizing our public officials and vice president kamala harris is no exception for that. unfortunately i didn't get her perspective because she declined to talk to me unlike the other women who ran in 2020. at the same time i think people who are defensive of her and critical of her all come at it from the same place, which is because she looks different than everyone else who had this job pfr her, there's a fundamentally unfair expectation she should be rewriting the role. if you're doing it correctly, people don't hear from you at all. in part because we filter her through the lens of someone who ran for president before or could run again, we see her as someone who has the eye on the future when in fact she's doing the job of vice president every day, and doing it in a moment where reproductive access and so-called women's issues are

front of mind for so many voters. you see in polling it's an energizing issue, and fact that kamala harris can speak to this, firsthand experience, that's something we never had in the vice presidency before. it's the highest position a woman has reached in our government, and in term of what it means for the future, republicans and democrats told me it hopefully makes the road smoother for anyone who comes after, because americans are getting to see what a woman in high office look like. >> important new book, important body of reporting. "electable" is out now. ali, congratulations and thanks for spending time with us to talk about it. >> thanks, nicole. >> quick break for us. we'll be right back. ack.

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