thanks for joining us tonight on "360." donald trump just wrapping up a large rally tonight in swing state, colorado. he spoke for about an hour, touching briefly on that "new york times" story and how little he might have paid in taxes over a spam of 18 years. there's that, as well as breaking news on a batch of new polling and more. our jason carroll is at the rally site in loveland. just north of denver. so trump addressing a huge crowd there. really enthusiastic. what did he say specifically about taxes? >> reporter: once again, donald trump, as he did in his rally a little earlier in pueblo, trying to turn the tables on this whole tax controversy, anderson, basically saying that he used the tax laws that are in place to beat the system. he said, basically, quote, he said, my job was to minimize the

tax burden, not only on himself, but also on his family. and when he addressed the crowd here, anderson, he freely admitted that he benefited from the system that's in place. >> the unfairness of the tax laws is unbelievable. it's something that i've been talking about for a long time. you've heard me talking about it. despite being a very big beneficiary, i must admit. i am. i am. i'm a big beneficiary. but you're more important than my being a beneficiary, so we're going to straighten it out and make it fair for everybody. i understand the tax laws better than almost anyone, which is why i am the one who can fix them, and that is what i commit to you. i will do it.

as a businessperson, i've legally used the tax laws to benefit, really, i mean, it's to my benefit, and to the benefit of my company, my investors, my employees, my family. >> he also had, anderson, trump surrogates like former new york city mayor, rudy giuliani, chris christie, some of the surrogates out there, basically saying, look, donald trump is a financial genius for what he did, but going forward, what the gop is going to have to sort of grapple with is, if it's okay for someone who's rich to beat the system, is it then okay for someone who's poor, possibly, on public assistance, to be able to legally beat the system as well? maybe that will be a discussion going forward. we'll see. but as for what happens right here, in this room tonight, the crowd really seemed to buy into donald trump's explanation. >> turning to his speech, i understand he also spoke about clinton as well as sanders?

>> reporter: he did. we heard a lot of criticism about hillary clinton, basically saying that she is the candidate of distraction. and something we've heard in reference to bernie sanders, he said that bernie sanders essentially signed a deal, what he said, signed a deal with the devil. it's interesting to hear him call hillary clinton a candidate of distraction, that she likes to focus on small, petty things. that's interesting, because as you know, his own supporters have accused trump as being the candidate of distraction. they wanted him to get off criticizing like a former miss universe and on to addressing the issues heading into the debate. >> jason carroll, loveland, colorado, thanks. from here on out, you can pretty much map out the days of the candidates in swing state by swing state. new polling in a number of those battleground states, like ohio, where hillary clinton joined the battle. more from jeff zeleny tonight. >> reporter: hillary clinton

returning to ohio for the first time in more than a month. >> hello, toledo! >> reporter: just on time to seize on donald trump's taxes, or as she said, his lack of paying them. >> in other words, trump was taking from america with both hands and leaving the rest of us with the bill. >> reporter: clinton is touting a "new york times" report that says trump may have avoided 18 years of federal taxes, after declaring a $916 million loss on his 1995 returns. she used it to raise more questions about one of his biggest selling points, his success as a businessman. >> yesterday his campaign was bragging it makes him a genius. what kind of genius loses $1 billion in a single year? >> reporter: she's trying to erode trump's ohio advantage, and win over voters without a college degree, who are overwhelmingly siding with him. a new quinnipiac poll today shows trump up by five points in ohio. she's made such infrequent visits to this key battleground state, the toledo blade wrote last week, where is hillary?

in two stops across ohio today, clinton pushed back hard, saying her policies would benefit working class voters far more than trump's. >> and you know, he has been dissing america in this whole campaign, right? he talks us down, he makes disparaging comments about our country. >> reporter: she's opening a new superstar endorsement will also help. >> i hope to be elected president, but i know here in ohio, lebron will always be the king. >> reporter: cleveland cavaliers' basketball great, lebron james, said the children of his native akron, and all cities, need clinton in the white house. he wrote, hillary is running on the message of hope and unity that we need. as hillary clinton tries to build momentum for the second believes there may be a new believes there may be a new opening for those white working class voters here in ohio and elsewhere that they have struggled to win over. they believe that tax returns and the questions raised by them

could give some of these voters a chance to give hillary clinton a second look. anderson? >> jeff zeleny, thanks. new polling from more than just ohio, where donald trump has managed to increase his lead from last month by 8 percentage points. plus, new cnn/orc national numbers showing hillary clinton showing a 5% lead. her gains coming largely from men, where she's shrunk a 22-point gap. to just five points now. now let's bring in tom foreman who's been doing the heavy lifting all day. what's the breakdown, tom? >> let's start with the big electoral prize down here. quinnipiac looked at florida, the sunshine state, where clinton came from a deadlock a month ago to now have a lead, 46% to trump's 41%. people there thought she won the debate and they're rewarding her. johnson at 5%, stein at 2%, by the way. if you move a little bit north up here to the light blue state, virginia, same sort of story. people thought she won there. she's now at 42%, trump is at 35%. importantly, she made gains with

millennials and with independent voters there, both groups, she said, she really needs. but let's move up towards that rust belt, where jeff was just a minute ago. in pennsylvania, different story. they still think she won the debate, but not nearly the kind of balance she wants up there. she's at 45%, trump was still at 41% in pennsylvania, where he's been pushing that message that the entire rust belt has been hurt by her policies, particularly on trade, and i'll tell you, anderson, across the line in pennsylvania, lebron james doesn't have as much influence. >> what about the western battlegrounds, any movement there? >> it's very different out in the west. different issues to consider. for example, nevada over here, in yellow, this is a place that democrats count on, having a strong showing, and trump gave them a little bit of a scare. so they rallied their union folks out there and said, you need to come out and support this democrat. that seems to be paying off. she's now at 44% compared to 38% for trump in a suffolk poll out there.

and if you move to colorado, light blue over here, same situation. trump made a run at it, had them a little bit nervous, but big surge by clinton. she is now very comfortably at 49% to 38%. remember, colorado voted for barack obama, the democrat, in 2008, and 2012. it looks like coloradans may be ready to go that way again. anderson? >> tom foreman, thanks. we're breaking it down. after weeks of warning viewers that polls really start mattering now, here we are, back with the panel. jeff, let me start with you. with these polls clearly not moving in a direction that's great for trump, without florida, pennsylvania, and nevada, can he win, in your opinion? >> he certainly needs these states. he needs them, as an unbiased pennsylvanian, he needs pennsylvania. he was just there on saturday. huge crowds. the harrisburg "patriot-news" ran a whole story saying that democrats are making a huge mistake underestimating him, because these people, i mean, not only as he's done, and i've

been to two of these things myselves, not only are these huge arenas filled, there are thousands outside that can't get in. hillary clinton will be in harrisburg in the next day or so, we'll see what kind of crowd she gets. >> i remember six weeks ago, john king showing the electoral map, saying that trump only had a slim window of how to get to 270. then all of a sudden within a matter of weeks, it seems like there were multiple paths, now here we are saying these latest polls show it's closing down for trump. >> there was still only the path through florida, ohio, pennsylvania. and jeffrey's from pennsylvania. this will shock you, but neither of us have a life, so this weekend he was e-mailing me from pennsylvania. he went to manheim, p.a., lancaster county, a population of less than 6,000, and drew more than 6,000. a guy like me says that's pretty impressive. but what we show in the polls is his command of college-educated white people is starting to erode. >> he still wins by 22. >> president obama was re-elected comfortably losing

them by 31. college-educated white people, which no democrat has ever won -- >> you've always focused on that group. >> just disaggregated my fellow white people. i don't know if people can see, but i am white. and hillary is now 13 points ahead among college-educated white people. i don't know if can sustain that but the president lost them by 12 and still lost re-election. it's a very difficult thing for both candidates, but for trump it's much harder. his path is much more narrow. van? >> and all this stuff makes me very happy. and i was very happy a couple of weeks ago. and then i was very sad, then i was very happy, then i was very sad. so -- >> i'm here to make you sad. >> obamacare covers that now. >> it's the only thing it covers. >> what i think is obvious to me, when donald trump does dumb stuff, he just bleeds off

support. >> yeah. >> you've got people out there who want to support this guy, but he gives them, you know, nausea, when he does crazy stuff. and so hillary clinton has done a brilliant job. she looks great, she's loose, she's giving us a lot of confidence. but i think a lot of what's going on here is, when he jumps on the pogo stick and acts crazy, people know. >> kayleigh, do you think this is sign that he lost the debate. he keeps saying that online polls say he won. is this a sign that most people thought he did badly? >> i think that's part of it. i think he didn't prosecute the case against hillary clinton as strongly as he could have. but it is worth mentioning. i was by van seven days ago during one of his sad periods, when john king was up there saying, there are now multiple paths to 270. >> it made you a little happy to see van sad. >> it did. we've had two historically unfavorable candidates, and we're seeing a volleyball back and forth momentum. and it just shows that anything

can change on a dime in seven days. these debates are crucial, they're important -- >> do you agree with that, andre? it is this back and forth, which is -- >> absolutely. it is -- for political wonks, it's actually competitive. it's impressive that many people are paying attention. i think missing almost a brexit situation. when you look at these rallies, the people that are coming out that never get involved in politics that are coming out in droves for donald trump, that will be an impact. the other thing is the minority vote. everybody, most media pundits have said, he's going to get 1%. every poll now is showing much greater than 1% and he has made inroads there. >> maria? >> that i'm not so sure of. but i will say, a day is a lifetime in politics. anything can happen. so what i would say to democrats is what i've said from the very beginning. let's pretend she's ten points behind, because we still need to mobilize all of our people. clearly, she needs to get millennials. she needs to get all of the voters of color. but i do want to point to one thing that i think is happening, and that is starting to sink in and to become part of the trend that is very dangerous for

donald trump. he started after the debate, with the alicia machado debacle, right? he could not get out of that. we were talking about that just yesterday. that is starting to sink in. to who? to critical demographics that he needs. latinas, women, even men who have daughters, who have sisters, who have mothers, who understand what it is to have this language that is so demeaning to women, that is sinking in. this tax issue is going to sink in, about how this is somebody who might talk a nice populist game, but at the end of the day, he doesn't give an "s" about the working people. >> clinton is still five points behind in ohio? >> yeah, the trade issues there, she's not been able the to recover from. sanders does better on those issues a lot better than she does. but what's so interesting, you watch donald trump, when he's giving that speech, there's an endearing quality there. when he goes what, you know, i am a beneficiary. that's sort of the billionaire, blue collar billionaire kind of

person that people like. that's different than the gordon gekko kind of campaign. he goes back and forth, aw, shucks, maybe you should benefit too. and i think what happened on that debate stage, there was a moment when you saw that side of him and i think that's going to stick. >> and hillary's speech in toledo was a bit more populist than the wonky hillary we normally get. this is why it's good to go to ohio. i'm glad the "toledo blade" was attacking her for not coming there. she needs to be out there with blue collar white folks. having lebron james does not hurt at all with any voters. >> in terms of the upcoming presidential debate, do you think donald trump is going to practice? >> he has to. look, he has to. because you have to prosecute

the case against hillary clinton. >> which i think -- and you raised this, that he did a good job of that early on in the debate, particularly on trade issues. >> you are not going to have a softball given to you. you're not going to have a moderator say, tell me about hillary clinton's e-mail server. >> wait, who's the moderator? >> if we only knew. >> you're not going to get that softball. what hillary clinton did effectively was she was given a question about finances and turned it around -- >> to make it about trump. >> you have to have that skill set. >> up next, how donald trump and other real estate developers in the past could use the law to pay far less in taxes than most americans and maybe even today, speaking of most americans, do you know these two individuals? and which one is which? see how many voters are stumped by the vice presidential candidates, governor mike pence and senator tim kaine. sureor put themhave ston a rack.e tires. but the specialists at ford like to show off their strengths: 13 name brands. all backed by our low price tire guarantee.

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well, donald trump said he brilliantly used the tax code to his own advantage, but now says he'll be working for all americans to change it. hillary clinton is questioning his head for business after declaring nearly $1 billion in corporate losses in 1995. how this ultimately plays out remains to be seen. he spoke about it again tonight in colorado and touting his business skills in what he painted as some very tough times. >> the news media is now obsessed with an alleged filings from the 1990s -- a along time ago -- at the end of one of the most brutal economic downturns in our community's history. the conditions facing real estate developers of the early

'90s were almost as bad as the great depression in 1929 and far worse than the great recession in 2008, which was nothing compared to the early '90s. these tough times were when i performed my best and enjoyed it in a certain way the most. the economy and the banks collapsing, the government was a mess, but i enjoyed waking up every single morning to go to battle and it was battle. >> and back with the panel. paul, you talked about this in the last hour. i find it really fascinating, as someone who is involved with a pro-clinton super pac, you're actually putting money on this. that you believe this resonates so deeply with voters that it's worth running commercials. >> right, a couple of things. there's the fundamental argument and four words that almost everybody in america agrees with, and they are, the system is rigged. the system is rigged. nobody argues that trump rigged the system. he didn't cause it. he isn't running the tax code.

but when he exploits it like that, i think it undermines his populist appeal. and when he says, it makes me smart, that kind of arrogance that van was talking about a little while ago, it really alienates voter. 61% -- a gallup poll earlier this year say, yeah, the rich should pay more. the next step on this, you want my prediction of where this is going, democrats like me will come out and say, now let's look at what trump's plan is on attackses. here's what it is. it cuts the estate tax to zero. a guy who inherited a vast fortune now thinks other heirs should pay nada, zip. a multitude of other tax codes in there all for the rich. and in fact, there's a net increase for the middle class. so i think when you start plowing through what would he does as president -- we know what he did as a businessman, he exploited a rigged system in a shocking way, but as a president, he would actually make a bad system worse. >> do you agree with that, kayleigh? >> no. i would love to talk about financial corruption. and why i don't think it will work is there is ample material for hillary clinton. we can talk about her taking millions of dollars in speaking

fees at college campuses, feeding off of student loans that are paid by students who now have a ton of debt or millions from foreign governments, foreign governments, by the way, that aren't that friendly to females or the homosexual community. we could go into all of this. there's so much material with clinton. so an effective donald trump in a debate will lob back with this information. >> yeah, yeah, he is going to go after this entire -- hillary's paying taxes, taking advantage of the same thing that donald trump took advantage of. and the point is, she's saying, elect me because i'm experienced. part of that service comes as a united states senator. if the system's rigged, she had a chance to change it. and she didn't do it and she's benefited from not changing it. >> van, is that an argument that you think will resonate? >> well, it will for some people. but there's a real big false equivalence there, and it's -- between this. i'm not great at math, but zero versus 30%. zero taxes, which is donald trump, 30%, which is hillary clinton.

and she did take a deduction on $770,000, which made her very rich -- no, actually, it got her $3,000. so i don't think if we go back and forth enough times -- >> you know she can double her own taxes, you know that? >> hmm? >> she wants to tax the rich, the irs takes your money. anybody can raise their own taxes. i don't understand if she feels so passionately about this, why she doesn't do that. >> i'm so glad you actually raised that, because she actually did not take advantage of all of her deductions. and i think that's a very good point. >> she did -- she could have paid even more than that. i don't understand why she doesn't. >> i think a couple things here. i think if you're just a normal person, you're watching this situation, and you're trying to figure out who understands me. not who understands the system. i'm sure they both understand the system. but who understands me. the fact that donald trump can't figure out that ordinary people are going to have a lot of heartburn and rugburn about this, he has somehow convinced a big section of the country that

he is just like them. that's an act of pure political genius, that is genius, but it's getting eroded over these last few days. >> because i think americans are starting to see the reality of the kind of life that he led and the arguments that he is making for why they should hire him to be commander in chief. and they are crumbling before our eyes. the fact that he was a good businessman. he's complaining about things being tough business wise. in 1995? the economy is going gangbusters. everybody was doing well. so, he lost almost $1 billion -- i'm sorry, not a good businessman. he declared bankruptcy six times. i'm sorry, not a good businessman in most people's eyes. and two things i think are critical in the poll that just came out. hillary clinton is beating him heads and shoulders above where he is in terms of the candidate who understands middle class voters. that is a critical piece. she has led so far and she's like up 13 points, even from where she was before.

in addition, majorities of donald trump's supporters believe that paying your taxes is a civic duty. >> maria, the counterto this argument is, if hillary clinton were such an experienced politician and such a great secretary of state, why is the world in this mess? why do we have all these -- why is the tax code a mess? her on-the-job performance has left a disaster. colin powell of all people said that she screws up. >> listen, i admire hillary clinton greatly -- i admire hillary clinton greatly, but at no point was she god, emperor of earth. at no point was she the -- >> but she could propose legislation -- >> and she did plenty of that. >> andre? >> she has no real accomplishments as a united states senator. other than naming a courthouse. >> that's not fair. >> she talked about creating tens of thousands of jobs in

upstate new york, but how many did she create, van? none, they lost jobs. >> she also extended benefits for soldiers who were in the national guard, not just in the u.s. army. she did a lot on homeland security and national security, in the senate. but on the tax question, she opposed the bush tax cuts. which rolled back her husband had this radical idea that the rich should pay more and the poor should pay less. and the economy boomed. and bush reversed that and we went into a massive recession. thank god president obama came in and went back to the policies -- >> she voted to raise -- >> -- but 20% of the people of this country pay 85% of the income tax. so i know democrats love to pick -- >> they have the most income! cigarette smokers pay all the cigarette taxes. >> how much do you make them pay? >> we've got to end it there. just ahead, the quirk in the tax code that may explain how a nearly $1 billion loss recorded by donald trump in 1995 may have been a write-off of money actually borrowed from others. we'll explain that, ahead.

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welcome back. donald trump often says he knows how to win. it's a line he uses over and

over in his speeches. but just five weeks from election day, the spotlight is on the report from "the new york times" that trump's loss of nearly $1 billion in his 1995 tax returns. trump has said he knows the tax code better than anyone and has used the tax laws brilliantly. tonight, senior investigative correspondent drew griffin drills down on how a loss that huge may not have been a loss at all, at least not in the way that most of us would think. >> they are just three pages hoff what appears to be donald trump's state tax returns from 21 years ago. hardly enough to know the real picture of donald trump's wealthy in taxes, but it is this stunning figure that has led to massive speculation, an almost $916 million loss. for what? trump isn't saying. but in the backward logic of real estate developers, complex tax laws and the lawyers who exploit them, it could be that trump has become wealthy, that he wins by losing. >> mr. trump was a spectacular loser.

he lost a lot of money from the casinos. he lost a lot of money from trump shuttle, the airline shuttle. and he lost a lot of money from the plaza hotel in new york, across the board, losing money, apparently. now, some of those losses may have been inflated by the generous tax sheltering that is afforded real estate developers and active managers of businesses. >> reporter: we can't see donald trump's tax records, but experts speculate the $960 million loss may not exactly be a loss at all, at least not a loss of trump's money. richard lipton, a real estate tax expert in chicago, says a quirk in an old law since changed in 2002, so favorably benefited real estate developers, that it is highly likely donald trump's 1995 write-off was actually a write-off of borrowed money. >> there was basically a real estate depression at that time. and the way the law worked at that point in time, if the

losses were funded by debt, the losses would flow through the to the developers, so you could easy see big numbers. i had one client who had a loss over $950 million during that time frame. individual, just like mr. trump. >> reporter: how did it work? take this simple example. a real estate developer wants to build a $100 million building. he puts up just $1 million of his own money and then borrows $99 million from a bank. if the entire project goes belly up, the bank loses its $99 million. the developer loses his $1 million, but on his tax return, that real estate developer can write off the entire $100 million loss if the bank writes off his debt, which happened a lot. lipton, interviewed by speakerphone by chicago, says it was an unintended gift from a poorly written tax code. >> that was the quirk in the law, drew. the taxpayer did not have to

pick up the cancellation of debt income, he just got the loss. >> i'm gasping. >> i understand why you're gasping, but it is just what the law said. >> reporter: taxpayer groups who keep an eye on congress and the bills passed here says none of this is surprising. >> that's exactly why we need to really look at the whole tax code and do a comprehensive reform and make decisions based on math, you know, kind of how much money do we need to raise to pay for the government that we collectively want? >> drew, i'm so glad you did that explainer, it really helps me understand and i think a lot of people. it sounds as if trump may well have been taking those big write-offs based in large part on other people's money or the bank's money. is there any way to know for sure? >> reporter: there's certainly a way to know, if donald trump would just release his taxes. show us what a genius he is and how this tax strategy works. but right now we have three pages from a state tax form, 21 years old, and the rest of all of this is all speculation on what it means.

>> drew, there was some news today as well about the trump foundation. >> yes, the democratic attorney general from new york over the weekend sent the trump foundation a letter saying, listen, you need to cease and desist any solicitation of money, because you are not properly registered with the state of new york. it turns out that the trump foundation hadn't filed the proper paperwork to be a legitimate charity in the eyes of the state of new york, so the attorney general there says, look, you can't raise anymore money until you do. he continues to investigate, the trump foundation, and i say democratic attorney general of new york, because part of the response from the trump campaign was to raise an allegation that this may be more politics than substance, although the trump campaign says, listen, we are going to comply with the state of new york and we are going to comply with the attorney general's investigation. we will get the paperwork filed. >> drew griffin, appreciate the debate. just ahead, a revealing pop quiz in central park, how many

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actually looked like. at this time tomorrow night, mike pence and tim kaine will be facing off in the first and only vice presidential debate of this election. neither is new to politics. they both have a lot of experience behind them. so they'll be familiar faces to everyone who watches tomorrow night's debate, right? maybe not. here's randi kaye. >> reporter: it appears the vice presidential candidate has some work to do. >> honey, what's the other guy's name? mike pence and who else? >> reporter: in new york's central park, we showed people pictured of the vice presidential candidate's pics and more often than not got a blank stare. watch what happened when we revealed a picture of hillary clinton's running mate, tim kaine. >> who's this? long pause. >> i have no idea. >> who's that? >> uh, i have no idea. >> you're not starting out well. >> i know. i have no idea who that is. >> these women were so confused by kaine's picture, they asked strangers passing by for an

assist. >> you know who this is? >> yes. >> you're getting help from strangers. >> can you help us out? >> he's somebody's running mate. >> they even struggled to name mike pence after i offered up his initials. >> m.p. nothing. pence. does that sound familiar? mike pence? >> no. >> and they still weren't clear he was even running. >> definitely not. >> definitely not running? >> no. >> they had to guess on which ticket. >> is he republican or democrat? you have no idea? >> he looks republican. >> looks pretty republican to me. >> so that would mean he's running with donald trump? >> i suppose so. >> this guy wasn't clear on tim kaine's party affiliation. >> is he republican or democrat? >> he looks republican. >> he's a democrat. you had two choices there. >> yeah, i know, right. >> his initials are t.k. >> t.k. tim kaine? >> yes! >> oh, so that's tim kaine, okay?

>> so you've never seen him before? >> i have not. >> not only had he never seen tim kaine, but he had no idea what pence's first name was. >> who's this guy? >> that's tim pence, or john pence. pence. >> billy pence, whatever you want to say. are you asking me or are you telling me. >> that's pence. >> reporter: he knew what ticket he was on, but struggled with mike pence's home state? >> do you know where he was governor? >> arkansas? alabama? >> no. >> starts with an "i." >> indiana. >> there you go. nicely done, mark. thanks for playing. >> reporter: these guys failed the tim kaine geography trivia. >> do you know where he's from? >> indiana. >> ohio? >> two strikes. >> one of the states that matters. >> that's good! >> virginia, virginia! >> yes. nicely done. >> just to mix things up, i threw in this picture of new jersey governor chris christie. >> is he running? >> no. but he kind of looks like he's

running, though. he stands behind trump a lot. >> reporter: perhaps mike pence and tim kaine could use a little more face time standing by their candidates. randi kaye, cnn, new york. >> well, 24 hours from now, tim kaine and mike pence will have their chance to make a lasting impression on voters. joining me now, david gurden, also debate coach, bret o'donnell who served in charge of messaging. so pence and kaine serve for some facial recognition issues. is that a priority for them tomorrow night, getting their name and face out there, or is it more getting the message of their running mate out? >> it's both. any goal for any debate is for voters to get to know you. and for these two, the big question is, should something happen, got forbid, to either one of their running mates, are they fit to be president of the united states. they have to pass that competency test. and one thing for sure, voters have to get to know who they

are, because by and large, we don't know them. >> david, there's definitely daylight between pence and trump on a lot of issues. while he hasn't joined the call for the top of the ticket to release his taxes, pence personally did release his taxes. do you expect that to come up tomorrow night? and it clearly will on the democratic side. i don't know if the debate moderators will bring it up, but certainly kaine are. >> tim kaine is going to raise it more than once. >> he's going to wear it on his t-shirt, i imagine. >> you know, usually these are inconsequential affairs. people wake up the day after not knowing anymore about the candidates than they just did in central park today. but i think this is one of the few that you really have to say, this matters. it's not only the fact that we have two candidates at the top of the ticket, who are going into their 70s, among the oldest ever to be in the presidency, and therefore, the vice presidents have to be ready to

go. but it's also that this campaign is breaking open. toward hillary clinton. and mike pence's role is to try to reverse the momentum of the campaign. to have us talking about something two or three days from now that is not the donald trump's taxes or is not the foundation, but is about some of the issues that the trump team cares about, immigration, the economy, job creation. they've got to change the subject and change the momentum. >> bret, what do you think kaine's biggest vulnerability is? >> well, i think that one of the things that mike pence will go after is the difference between the two on a couple of essential core issues, like trade and even abortion and also on the use of military force. those are three big things that secretary clinton and senator kaine differ on. so we could try to drive a wedge there to expose those differences and talk about the position. you know, trump was fairly effective talking about trade in the last debate. if governor pence can change the conversation back to a trade debate, then the campaign's back on offense. >> david, i want to look ahead to the next presidential debate.

what do both candidates you think need to accomplish? and do you think donald trump is going to be able to change things out from the last debate? >> that's really good question, anderson, because i think if he does lose two in a row, it doesn't make much difference what happens on his third debate, unless there's some extraordinary event. so i think this one is one that trump needs to win. and we haven't seen any evidence so far that he's settling down and really trying to bone up and prepare himself in a different way. and he got swept last time because she was so much better prepared than he was. >> bret, we've seen a lot -- trump's had a rough go of it over the last day, a lot of ups and downs in t campaign. do you see the next debate as make or break for him? >> it's certainly a big debate. in 2004, george w. bush had a poor first debate and made a comeback in the second debate. last cycle, barack obama had the same problem, made a big comeback in the second debate. town hall debates are different from the regular podium debates. it offers trump an opportunity, but i do think that the pressure

is on him. >> yeah, anderson, it's also been true that the only times we've seen when someone lost the first debate and came back and won the second debate is when incumbents did that. an incumbent would lose the first debate. we've never seen a challenger lose, win a second, and come back to victory. >> why do you think that is? and why is it easier for an incumbent to have a comeback? because we know them more? >> yeah, they can always say, oh, we were rusty, we weren't quite ready. but the pressure's been on them in that second debate. i think both reagan and obama came back very strongly in that second debate. but challengers, you know, we make -- we judge people quickly and a lot of people made up their minds in that first debate. for donald trump to change people's minds and to say he's really a better debate and more ready for the office, big hill to climb. that's why i'm amazed he's not bunkering down and really getting ready for it. >> bret, the question is not just on issues, but will donald trump continue to take the debate if secretary clinton

dangles it h front of him like he did the last time? >> that's the big question. he's got to stay on offense the entire debate. winning or losing these things is based straight on offense. who is the more aggressive, in the debate, able to prosecute their attacks better? that's what these are about. if donald trump can do that, he can turn the tide. he had plenty of opportunities in the last debate and just missed so many wide open opportunities for himself. it wasn't that secretary clinton was fantastic, it was that donald trump took the bait and stayed on defense. >> bret o'donnell and david gergen, good discussion. appreciate it. with less than 24 hours to go until the vice presidential debate, we'll take a look at the best and worst moments from the vice presidential face-offs, including this from the 2008 campaign. >> nice to meet you. can i call you joe? thank you.

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record 84 million people watched the first presidential debate. tomorrow night is the vice presidential candidates chance to face off, the only chance for them to take center stage, an opportunity to come out of their running mate's shadows. >> now in the spotlight it is

high stakes for the vice presidential contenders to soar or stumble. >> with all due respect, that's a bunch of malarkey. >> reporter: there have been the one-line zingers. >> i think senator dole has richly earned his reputation as a hatchet man tonight. >> reporter: which go on to become the breakout moment of the debates. >> senator, i served with jack kennedy, i knew jack kennedy. jack kennedy was a friend of mine. senator, you're no jack kennedy. >> reporter: and miscalculations like admiral stockdale in 1992 trying to poke a little fun at his own experience. >> who am i? why am i here? i'm not a politician. >> reporter: that fell flat and opened up their ticket to late night jokes instead. >> who am i? why am i here? >> you're the admiral and you're taking a joy ride. >> reporter: in 2008 the

relatively unknown first-term governor from alaska was facing questions over her experience, going up against a well-established u.s. senator joe biden. >> can i call you joe? >> reporter: those six words within the first few seconds of the debate created her big moment, seen as a successful move to disarm her competitor. >> say it ain't so, joe. there you go again. >> reporter: the first one who to be a the veep stage in 1984 capitalized quickly on her opponent's first misstep. >> let me help you with the difference between iran and the embassy in lebanon. geraldine ferraro calling george h.w. bush out for that on stage. >> i almost resent your patronizing attitude that you have to teach me about foreign policy. >> reporter: the vice presidential debates provide a key test for the person who could be a heartbeat away from the presidency, answering the question on voters' minds, are they capable to assume the job

as president. >> she doesn't have the stamina, and i don't believe she does have the stamina. to be president of this country you need tremendous stamina. >> as soon as he travels to 112 countries and negotiates a peace deal -- >> reporter: another key question that could factor in more this year as issues of health and age for both donald trump and hillary clinton swirl. >> the main quality that you want is somebody that can be a great president if something happens to you. that's got to be -- don't you think that's got to be number one? >> reporter: a duty both candidates seem to be taking seriously. >> i want to be sure that whoever i pick could be president immediately if something were to happen. >> reporter: cnn, farmville, virginia. >> tomorrow night's vice presidential debate 9:00 p.m. eastern here on cnn. we will be right back. sureor put themhave ston a rack.e tires. but the specialists at ford like to show off their strengths: 13 name brands.

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quick reminder, we have two big debates coming up this week, first tomorrow night between vice presidential candidate. mike pence and tim kaine. begins 4:00 a.m., debate starts at 9:00 p.m. sunday, abc martha raddatz will be moderating. a lot on the line. a campaign in the balance. right now, "cnn tonight with don lemon." not such a good time to be donald trump. this is cnn tonight. i'm don lemon. they say bad news comes in threes.

first, a mystery tipster sends several pages from trump's 1995 tax returns to the "new york times" revealing the multi-billionaire wrote off almost a billion dollars, $960 million in losses. donald trump says that just proves he's a great businessman. >> i have legally used the tax laws to my benefit, and to the benefit of my company, my investors and my employees. i mean honestly i have brilliantly -- i have brilliantly used those laws. >> well, of course, hillary clinton disagrees. >> what kind of genius loses a billion dollars in a single year? this is trump to a t. then new york's attorney general orders the trump foundation to immediately stop fundraising saying it is in violation of state laws. and then there's this.