>> yeah. >> it is certainly a warning. thanks for that report, jim sciutto. really appreciate it. i'm brianna keilar. thank you for watching. "erin burnett outfront" starts right now. "outfront" next, breaking news, donald trump bragging about using tax laws, quote, brilliantly, as a new cnn poll shows the debate took a toll on the republican nominee. plus how did trump declare almost $1 billion in losses and what does that say about him as a businessman? my guest linkedin co-founder, billionaire, reid hoffman. and hillary clinton's leaked comments about young people living in their parents' basements. will it hurt her? let's go "outfront." good evening, i'm erin burnett. "outfront" tonight, the breaking news, donald trump about to rally supporters in a crucial swing state. colorado. trump fighting back against "the new york times" story charging that in 1995 he reported a nearly billion-dollar loss, a

loss that could have meant that trump paid no federal income tax for years and years and years. trump has not denying the "times" report and today doubled down on his defense. >> i have legally used the tax laws to my benefit, and to the benefit of my company. my investors and my employees. i have brilliantly used those laws. i have often said on the campaign trail that i have a fiduciary responsibility to pay no more tax than is legally required. >> with just 36 days until election day, trump is on defense because a new cnn national poll breaking tonight, taken after the first presidential debate, shows clinton with a five-point lead over trump. now, that's a seven-point swing from our last poll one month ago. so seven points in just one month. in four of five new state polls today, clinton came out on top. moments ago, clinton campaigning in battleground ohio trying to build her advantage.

hammering home the report about trump's taxes. >> he then has taken advantage of every single element of our tax code, of our economy, that he could. and along the way, along the way, he has stiffed people, small businesses and workers and contractors. >> sara murray is "outfront" tonight at the trump rally in loveland, colorado, as it's about to begin. sara, donald trump on the defense about those taxes spending a lot of time talking about it today. >> reporter: that's right, erin, and he didn't go so far when he was in pueblo earlier today to say or admit he's not paying federal income taxes but heard him talk about how he worked the tax laws to his benefit and even maybe the somewhat credible argument that he has a fiduciary responsibility to keep his personal taxes low. donald trump stumbling from an

underwhelming debate performance, straight into a firestorm over his finances. >> the unfairness of the tax laws is unbelievable. it's something i've been talking about for a long time. despite, frankly, being a big beneficiary of the laws. but i'm working for you now. i'm not working for trump. >> reporter: today, hillary clinton is seizing on a "new york times" report that reveals a portion of trump's 1995 tax return. showing the billionaire businessman declared a $916 million lorss, a loss so large t could have allowed him to avoid paying federal income taxes for nearly two decades. >> while millions of american families, including mine and yours, were working hard, paying our fair share, it seems he was contributing nothing to our nation. >> reporter: today, trump slamming the tax code. even as he admits it has given him a boost. arguing as a businessman, it's his responsibility to pay as little to uncle sam as possible.

>> i have brilliantly used those laws. i have often said on the campaign trail that i have a fiduciary responsibility to pay no more tax than is legally required. like anybody else. >> reporter: and dismissing his 19the 9 0s losses claiming the eight-month recession of the early the '90s was far worse than the 18-month-long great recession. >> the conditions facing real estate developers in that early '90s period were almost as bad as the great depression of 1929 and far worse than the great recession of 2008. not even close. >> reporter: trump's vigorous defense of his business practices comes as he faceses a new wave of scrutiny over his charitable foundation. the new york attorney general has ordered the trump foundation to halt its fund-raising. amid reports it failed to participate in routine audits required by state law. while trump's campaign questioned the attorney general's political motive, they said the foundation will

cooperate with the investigation. >> go donald. >> reporter: in the midst of a tumultuous stretch, the gop nominee is embracing his underdog status. >> when people make the mistake of underestimating me, that's when they are really in for their biggest surprise. >> reporter: and looking to turn up the heat on clinton. >> hillary clinton has never created a single job in her entire life. >> reporter: now, donald trump touched another nerve earlier today when he seemed to suggest at a veterans event that veterans who commit suicide when they have ptsd when they come home from war can't handle the stress of war. now the trump campaign quickly tried to clarify that remark. michael flynn, retired lieutenant general who's supporting donald trump said he was simply trying to highlight the challenges that veterans face when they come home and accused the media of trying to take donald trump's words out of context. >> all right, sara, thank you very much. we're going to play that in just a couple of moments.

first, though, the polls. new cnn poll showing a solid gain for hillary clinton. as we said, it was a big swing from a month ago in the poll. sunlen serfaty is "outfront" in virginia. what are you seeing in these polls? >> reporter: it's interesting here, erin, hillary clinton seems to be drawing a majority of her support from female voters, although that support has largely stayed in tact. stayed the same over the last month. donald trump gaining about a few points, but still very behind hillary clinton in terms of the women vote. but the good news for here for team clinton, within these poll numbers, is really if you look at the male vote, that's where she really does seem to be expanding her support and drawing her biggest boost in the last month. if you look at the numbers from early september, she was so far behind donald trump in terms of support from men. only about 32% support there. that has jumped 8 percentage points to 40% in just the last month, and it's important to see these side-by-side comparisons to this big jump by team clinton in the past month in terms of

men. really shows that she's really closing that divide, really catching up to him in terms of support from men. she's now only ahead by 5 percentage points. >> obviously that's significant, sunlen. in terms of the tax issue, the poll looked at whether voters believe trump should release his taxes. what did the results show? >> reporter: they absolutely showed that voters want to see donald trump's taxes released. 73%, nearly 3/4 of voters say they want those returns to be released and this is where it actually gets a little more concerning for team trump here. 57% of those polled said that they believe he's withholding his tax returns because they believe he has something to hide. only 33% say they believe it was because he's under this audit which, of course, is what donald trump says, why he explains he can't release his tax returns. and the majority of voters, 79%, believe that it is someone's civic duty to pay taxes and important to note that 79%

majority among trump supporters, too, so his supporters are saying this is someone's civic duty to not only release their tax returns but pay taxes. again, this was all done before "the new york times" story this weekend. certainly amplifies the issue before, certainly on voters' minds before now and more so. >> all right, sunlen, thank withdrew very much. "outfront" now corey lewandowski, former campaign manager for donald trump,. phillip bump, "washington post" political reporter. david gergen, former presidential adviser for four presidents. let me talk first, corey, the crucial issue here of time. this is what this is a lot about now. you have 36 days left. this is a poll that shows a seven-point swing in favor of hillary clinton in just one month. do you have enough time? >> look, the national polls are important. but what's most important is the state-by-state polls. that's really what you have to focus on. >> four, five of those today. >> you have to tlolook at the states of north carolina, ohio, pennsylvania, florida. those four states make up the backbone of the trump campaign.

if he's going it be successful and get to 270 votes, he needs to win all 4 of those states. if he isn't going to win pennsylvania based on what the numbers say, he has to set a separate path forward. looks like the 2nd district in maine, nevada, new mexico. places like that. the national polls are important but not as important as the state-specific polls. >> all right. as we said, other than ohio, hefls ahead in ohio today, behind in pennsylvania, virginia, the other ones. the issue of time here, 36 days left. one month after the conventions, clinton was solidly ahead. a month later trump had taken fleet sever the lead in several national polls. are you worried the pendulum could swing the other way just as quickly? >> absolutely not. hillary has not been taking anything for granted. she has made an extensive effort to reach out to swing voters. not only doing rallies with people who have voted for her in the primaries. women's issues about women, minorities, millennials and now etch white men aeven white men

around to an understanding, there was a reality outside of the show that was the republican primary and quite entertaining and hitting home for people in the next few weeks we'll be electing the next president of the united states. do you want somebody who's prepared for the job or do you want somebody who words don't necessarily matter and says whatever he wants to say within the moment? that's -- the reality is setting in and i think people are starting to become aware particularly in swing states where you will see that hillary is up except for ohio, and she has a much stronger ground game and more extensive ground game and field operation to actually turn out these voters on election day. >> let's talk about the words he said, phillip, today, donald trump was speaking at a veterans event, a veterans rally and was talking about ptsd. you said sara say it seemed to imply he was says people with ptsd couldn't handle what they've seen in combat. let me play his full words so everyone can hear what he said. >> when you talk about the mental health problems, when people come back from war and combat, and they see things that maybe a lot of the folks in this

room have seen many times over, and you're strong and you can handle it, but a lot of people can't handle it. >> that's the full context of what he said. they're now trying to say he wasn't saying that some weren't strong enough to handle it. it is, of course, that does sound like what he was saying there. will that hurt him? >> i think the thing to keep in mind here is that the problem donald trump faces is he needs to expand his base of support. the reason he's not being able to expand his base of support is because people are concerned about his temperament. they're concerned about his qualifications. i think what you just saw there which seems to be at the very best a poorly phrased expression of support for veterans, at the very best it's poorly phrased. it will reinforce for people who are concerned about donald trump's candidacy, is this a guy we want sitting across from vladimir putin or president of some other nation who may say the wrong thing in that moment? what donald trump needs to do moving forward, read off the teleprompter as much as possible, avoid making missteps and making statements that can be interpreted in the wrong way. >> the issue with the taxes, though, here, goes to this.

the core of what he has said, corey, the argument you made for him is he is a businessman. he knows the tax laws, knew how to avoid them. knows how to do business in china, knows how to make others not do business. that's always been the core of his argument. on this tax issue, it's not that he avoided paying taxes which perhaps may be the problem, it's the fact he lost a billion dollars which may be the problem. here's how he's talked about his business acumen, david. >> i'm really a good businessman. i'm in business. i did a very good job, but i will say this, and people are very, very impressed with what i've done, the businesspeople. i was a world class businessman. now i'm a politician. >> does the loss, the $916 million loss which he does not dispute at this point, does that hurt him? >> absolutely. i mean, this is the first time we've had a real look into his taxes. he's been resisting that all along. >> yes. >> and what do we see? yes, i think we should concede up front he did not do anything illegally. yes, i think we should concede up front that it was illegal for the person who gave these forms

out to get them publiced. not "the new york times" but the person who gave them out. having said that, he just claimed today that he did this because he did great things for his stockholders. he did great things for companies. you know, "the new york times" report, itself, said, look, while he was avoiding taxes, losing almost $1 billion, and basically in a year or two, his stock price went from $35 to 17 cents. the shareholders took more than a haircut. they were devastated by it. small contractors who were working in these casinos, what happened to them? they got pennies on the dollar. employees, they got hurt. since that time, give him credit, he has rebuilt his business. >> yes. >> but if you look at that, i mean, then claim this is a genius at work when you lose $1 billion? hillary had every right to make that comment. >> very, very quick. >> two important factors. number one, "the new york times" wrote on october 25th, 19995, donald trump back. moreover, warren buffett, many

people consider to be the oracle of omaha, the greatest businessman in the country, tax loss in 2014, $873 million. $873 million. you're dealing with a world-class businessman in donald trump who in 1995, they say what his loss was. warren buffett this year -- >> he's not running as president. >> donald trump wasn't running for president -- george soros took a billi$1.5 billion loss. >> warren buffett is one of the first people, including bill gates, several billionaires when the estate tax was eliminated -- >> that's a separate issue. >> in terms of civic responsibility -- >> people aren't saying he's a bad businessman. this point of -- >> donald trump lost -- >> we're also taking donald trump's business acumen on faith. release your taxes. if that's what you're saying -- >> we're going to talk much more about this. the report that donald trump may have paid no federal income tax for years, how did he actually do it? well, the reporter who broke the

story who knows it all, my guest "outfront." america's mayor to top trump defender. why some are saying this isn't the rudy giuliani they know. and jeanne moos at debate night on "saturday night live." >> my microphone is broken. she broke it. picking up for kyle. here you go. you wouldn't put up with part of a pizza. um. something wrong? so when it comes to pain relievers, why put up with just part of a day? you want the whole thing? yes, yes! live whole. not part. aleve.

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bp engineers use robotic ultrasound technology, so they can detect and repair corrosion before it ever becomes a problem. because safety is never being satisfied. and always working to be better. breaking news tonight at a rally, donald trump fighting back over report he declared a nearly billion-dollar loss in 1995 that could have enabled him to avoid paying any federal income taxes for nearly two decades. >> it's my job to minimize the overall tax burden to the greatest extent possible which allows me to reinvest in neighborhoods, in workers and build amazing properties. >> tax issue raising new questions about trump's success as a businessman. we're going to talk to "the new york times" reporter who broke the story live in just a moment. but first, drew griffin is "outfront" with a closer look at trump's taxes. >> reporter: they are just three pages of 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 wealth and taxes. but it is this stunning figure that has led to massive speculation and almost $916 million loss. for what? trump isn't saying. but in the backwards 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's afforded real estate developers and active managers of

businesses. >> reporter: we can't see donald trump's tax records, but experts speculate the $916 million loss may not exactly be a loss at all. at least not a loss of trump's money. richard lipten, 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 to the developers so you could easily see big numbers. i had one client who had a loss over $950 million during that timeframe. 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 then borrows $9the 9 the from a bank. if the entire project goes belly-up, the bank loses the $99 million. on his tax return, the real estate developer can wry off the entire $100 million loss if the bank writes off his debt which happened a lot. lipton interviewed by speakerphone from chicago says it was an unintended gift from a tax code. >> that was the quirk in the law, drew. the taxpayer did not have to pick up the cancelation 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. >> erin, the bottom line is we really don't know what this loss was all about. we don't know if trump was a genius or a terrible businessman based on these three pages from state tax returns two decades

ago, but what is clear in so many cases like this involving donald trump, if he wanted us to know, we would. not just have to speculate. he could come forward with his tax records and explain this. obviously, that's not happening. he's refusing to release any tax returns while he claims to be under an irs audit. erin? >> all right. thank you very much, drew griffin. pretty stunning when you see the law. how broken our tax system is. suzanne craig broke this story for "the new york times." you got the pages from the 1995 tax returns anonymously. let me just start with this. donald trump saying he brilliantly used the tax returns. he's not disputing your report in any way. a question for you, though, because you've looked at these returns. the pages that you have. do you have any doubt in your mind that they are authentic? >> no, we don't. >> so you're sure this is the real deal. >> we got them, obviously it took a lot of work to get to the work where we were willing, we were ready to publish them, but we did a lot of reporting around it and we had the accountant who signed the documents, who signed them along with marla maples who

signed her name marla trump and donald trump verified them for us. we went and met with him and they were very familiar documents to the accountant. >> so you know these are real. now, a few questions about what's in them. when you talk about, you said he could have avoided paying taxes for 18 years. this a statutory thing, right? you got that many years at that time to use -- >> yeah, we haven't seen what he did with the loss that he could use, we don't have those taxes going forward. "the new york times" off don't put the word "could" in very many leads but in this case we were very careful because we simply don't know -- >> you don't know, he could have earned $1 billion the next year and it was one year or could have earned it over ten years or could have been up to 18 years. >> that's right. >> that's the big question right now, how many years. >> we were very careful, but we knew he had that in that year and he was able to carry that massive almost $1 billion forward and could have used it in future years to avoid income tax. >> so did you see anything in the documents that gave you any

inkling of how much he gave to charity? the big question mark out there still. >> we don't have the full return so we had three pages and there were some boxes that were checked no that were, you know, there's a lot, everybody's looked at the tax return. you can check do i want to give $5 to this charity or the veterans fund or the wildlife -- there was nothing checked yes on those boxes but we certainly do not have a full picture and there were other pages where most certainly we would get a better idea of what he gave to charity and we just didn't see them. >> so, the return address, i mean, here's the thing. this is -- i mean, i remember seeing, you said you actually check your mail and a lot of people don't. you sort of obsessively check your mail. this came in a paper manila envelope, return address from trump tower. does not mean it came from trump tower. >> anonymous envelope with three pages in it. >> so do you think this came from someone in the campaign, from someone who works in that building? do you have any sense at this point? >> we have been -- we made a list and we just -- there were so many people and it was hard

to begin to even wonder where it came from. our job became after we realized that that was going to be a very hard task was simply to either verify it or tear it apart, one of the two. we just started of this track of how can we verify it and also, you know, what's here that doesn't make sense and what does make sense. we hired tax experts to come in and take a look at it and phoned a lot of people. >> all right. susanne, thank you very much. pretty stunning report that you came out with. susanne craig broke this story. billionaire investor and linkedin founder reid hoffman on what the taxes tell him, is trump a genius or a bid businessman? and rudy giuliani, why is he attacking bill clinton for infideliti infidelities? >> you have your own infideliti infidelities. >> everybody does. "or something." and we don't just pull smoked chicken, bake fresh foccacia and hand-slice avocado. there's nothing "or something" about it.

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narrator: it wasn't that long ago. years of devastating cutbacks to our schools. 30,000 teachers laid off. class sizes increased. art and music programs cut. we can't ever go back. ryan ruelas: so vote yes on proposition 55. reagan duncan: prop 55 prevents 4 billion in new cuts to our schools. letty muñoz-gonzalez: simply by maintaining the current tax rate on the wealthiest californians. ryan ruelas: no new education cuts, and no new taxes. reagan duncan: vote yes on 55. sarah morgan: to help our children thrive.

tonight hillary clinton hammering donald trump over a report he hay not have paid federal income taxes for nearly two decades. >> today in colorado he claimed he brilliantly used the laws to avoid paying taxes. well, that just shows, number one, he is the poster boy, the

poster boy for the same rigged system that he would make even worse. >> this is a new cnn poll shows trump supporters are still more enthusiastic about voting for clinton. the democrat, though, has closed the all-important enthusiasm gap. suzanne malveaux is "outfront." >> here's my question, what kind of genius loses $1 billion in a single year? >> reporter: hillary clinton delivering a one-two punch at donald trump today. over his 1995 tax returns, knocking the gop nominee on the trail today in ohio over a bombshell report in "the new york times" that trump claimed a loss of $916 million that year which could have allowed him to avoid federal income taxes for 18 years. >> seems he was contributing nothing to our nation. >> reporter: and blasting her rival in a national tv ad. >> he didn't pay any federal income tax. >> that makes me smart. >> if he's paid -- if he thinks that makes him smart, what does he think of you?

>> how stupid are the people of the country? >> reporter: clinton is campaigning in ohio for the first time since labor day. with a new quinnipiac university poll showing her trailing trump by five points in the buckeye state. today, she basked in the endorsement of one of ohio's favorite sons, cleveland cavaliers superstar lebron james. >> i hope to be elected president, but i know, here in ohio, lebron will always be the king. >> reporter: the democratic nominee is trying to draw a contrast with trump on the economy. portraying him as out of touch with hardworking americans >> trump represents the same rigged system that he claims he's going to change. >> reporter: seizing on an audio recording of clinton's comments from a february fund-raiser, obtained from a hack into a democratic staffer's e-mail in which clinton tryinies to expla bernie sanders' appeal to his supporters. >> they're children of the great recession and they are living in their parents' basement.

that is a mindset that is really affecting their politics. >> hillary clinton thinks bernie sanders' supporters are hopeless and ignorant basement dwellers. are. >> reporter: sanders says it's important to look at clinton's entire message. >> there are young people who went deeply into debt, worked very hard, they got a good education, and yet they're getting out of school and can't find decent paying jobs. >> reporter: hillary clinton and her team are not taking donald trump's bait. those i talked to today say they're not addressing any of his talk regarding infidelity. clinton has identified what she sees as a -- to hammer him over the -- a window into his character, his sense of civic duty, and his business skills. erin? >> all right, suzanne u thank withdrew ve you very much. my panel is back with me. david, let me start with you. people took to twitter immediately when the news broke and started usin using #basementdwellers.

she didn't actually use those words. that's the one that caught on with people. the question is, will this hurt her? >> once again, it's bernie sanders who's come to her rescue. you remember that first debate, when he said, i'm sick of these damn e-mail stories and sort of took it off the table for her. it was an enormous gift to her. he could have -- >> yeah. >> and he came out rapidly in her favor and took a statement that could have been turned into a charge against her and, you know, she was belittling these people and all the rest of it and took it to a higher level. i think as a result, he gave her another gift. i think -- >> it's more than just taking it to a higher level, though, because it's looking at the context of the entire statement in which he talks about a generation, frankly, my generation, that is struggling with having a college degree, not being able to -- having no access to affordable housing, jobs that have -- this is the modern -- supposed to be the future backbone, economic backbone of our country. these are not people who are

getting $13 million small gifts from their parents to get started. these are not people who can even imagine the idea of having $1 billion to squander, let alone to -- this group of americans that -- less of perspective of what's actually going on. >> empathy in the hidden tapes. if you look at where her poll numbers are, compared to where barack obama was, she's getting absolutely destroyed. 17% of the people in the cnn poll under 35 are supporting gary johnson. if i were gary johnson, i'd be hitting those college campuses, i would be distributing -- if she wants to blame someone for the poor performance of the economy, why those people are living in the basement, she has to blame barack obama because he's the president of the united states. she's not willing to do that. she needs him as a surrogate. right now she's in between a rock and hard place. the bottom line is she can't blame -- if this was really her position, come out and say that

publicly as opposed to another hidden tape now released. >> on the issue of young people, she does lag with young people, it's a big issue for her. on the enthusiasm front, i don't want to say just young people, obviously it can be people of any age. enthusiasm, she has risen in the most recent polls. she's now up to 50%. it was 46% earlier this month. that's a significant jump and donald trump was at 58%, now down to 56%. significantly stronger than she is. that gap is not moving in a good direction for donald trump. does the enthusiasm gap mean votes? when people are excited to vote for her as opposed to against him? >> theoretically, i wouldn't put too much stock into it, you know, first of all those aren't huge changes. plus when we see a poll where hillary clinton is rising and donald trump is falling, one would expect to see more enthusiasm for hillary clinton. the real question for the democrats is the longstanding question for democrats which is can they turn people out? democrats tend to vote less frequently because the people who vote more are older and tend to be wealthier. that's not the democratic base. the democrats have to do everything they can to get out

the vote come november. regardless of what those enthusiasm numbers are. that's a longstanding problem that will be a problem again this year. >> quickly before we go, i want to play one trump campaign ad. i want to play one for trump. using all of clinton's own words against her. here it is. >> 50 points ahead. you might ask. >> maybe it's because the director of the fbi said you lied about your e-mails. >> there was classified material e-mails. >> maybe it's because your policies have allowed isis and terrorism to spread. or maybe it's because you call americans deplorable. >> effective? >> yes. i think it's pretty effective but that's not the point they want to make. this is the fifth anniversary of your show tonight. right? all of us want to congratulate you. >> well, thank you to all. it's a pleasure to have you with us on our fifth anniversary. i can't believe how time flies. all right. thanks to all. and next, we are awaiting donald trump who will be rallying supporters shortly in colorado. will he address the controversy over his taxes?

plus rudy giuliani, remember when he was america's mayor after 9/11 now a lightning rod on the campaign trail stumping for trump. >> there is just america! what happened to it? and jeanne moos on bad microphones, sniffing and the "saturday night live" debate. (crickets chirping) ♪ (jet engine) ♪ (heart beat) ♪ (water splashing) (rain drops) (engine revving) (tires on wet road) ♪ lease the exhilarating 2017 lincoln mkz for $349 a month only at your lincoln dealer. be the you who doesn't cover your moderate to severe plaque psoriasis. be the you who shows up in that dress. who hugs a friend. who is done with treatments that don't give you clearer skin. be the you who controls your psoriasis with stelara®

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a huge impact in my life. rudy giuliani fast becoming donald trump's top attack dog. the former new york mayor unleashing a series of personal and controversial attacks on hillary clinton. but is this the same giuliani once known as america's mayor? kyung lah is "outfront." >> shows you what a genius he is, how smart he is, how intelligent he is. >> reporter: rudy giuliani, trump supporter, defending the presidential candidate on his taxes. giuliani then said this. >> don't you think a man who has this kind of economic genius is a lot better for the united states than a woman? >> reporter: making the sunday morning show rounds, the former new york mayor trufrustrated moderators, on "meet the press" contending bill clinton's affair in the 19 90s is fair game even

for him, a man with his own checkered past. >> you have your own infideliti infidelities. >> reporter: months and lmonths of logic -- the giuliani of today, unrecognizable to longtime "new york times" columnist clyde haberman who followed the mayor for two decades. his speech at the rnc, for example. >> what happened to it? where did it go? how was it thrown away? >> with his arms raised, his mouth contorted. he looked, frankly, crazed. a lot of new yorkers including many who long admired him are really doubting who this guy is now. i do think what he's doing these days threatens his legacy. >> the situation is that two airplanes have attacked

apparently -- >> reporter: a legacy best remembered after 9/11, america's mayor, a steady hand for his city and his country who sounded a powerful note of unity and tolerance at the united nations. now working for a man who vows extreme vetting of muslim immigrants. >> this was not just an attack on the city of new york. or on the united states of america. it was an attack on the very idea of a free, inclusive and civil society. >> reporter: but giuliani remains a man who "daily beast" editor and chief john avalon respected and continues to respect. he was giuliani's chief speechwriter in the mayor's second term and says politics may be in the present, but history should recall the man of decades ago. >> i don't think rudy is being his best self and very often he's being called on to defend the indefensible, but i don't think it should define the totality of his career.

i think that's a disservice to history. >> avalon also adds this, that when election 2016 is over, when we have turned this page, that he will be remembered, his legacy will be defined not by these recent years but by those events like 9/11, by cleaning up new york. talent plenty of his critics certainly disagree, erin, they say, hey, look, we have 36 days left in this election, what is rudy giuliani going to say next? >> all right. thank you so much, kyung. "outfront" next, what do trump's taxes say about him as a businessman? well, we're going to ask entrepreneur linkedin co-founder billionaire reid hoffman. and jeanne moos on the most eagerly anticipated "snl" debate in years. picking up for kyle.

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if something doesn't seem right, so everyone comes home safely. because safety is never being satisfied. and always working to be better. donald trump about to rally his supporters as you can see on the screen in loveland, colorado. earlier today addressing the controversy over his taxes, insisting that he's brilliant for using the tax laws to his advantage. >> i have legally used the tax laws to my benefit and to the benefit of my company. my investors and my employees. i have brilliantly used those laws. >> and "outfront" now, billionaire reid hoffman, co-founder of linkedin, hillary clinton supporter, will donate $5 million to veteran groups if donald trump releases his tax returns before the final presidential debate in 16 days. reid, thank you so much for being with us again. trump reportedly declared, and

he does not dispute this, $916 loss back in 1995 that could have enabled him to avoid paying federal income taxes for nearly two decades. what's your reaction to that? >> well, a couple of things. the first is how important it is that we have that transparency, like, that's the precise reason why every credible presidential candidate over the last few decades has released their full income tax returns so people understand, you know, what their actual state of public affairs is, what their conflicts of interest is, what their charitable is, where they are. and this is the classic thing because my first reaction was, so, $916 million loss, that equals very, very successful businessman? that doesn't quite go together. and we'd love to see the whole picture to see what is actually true. >> so, as an entrepreneur, you know, you sit here in a unique position, right, you made your billions, yourself. does the absolute size of the loss, itself, say something to you about donald trump and his

business acumen? >> well, no one says i'm a successful businessman and then turns around and goes, and i lost nearly $1 billion. right? the whole goal is to make money, you know, that is what successful business looks like. successful business looks like, you know, paying your suppliers, not offloading, you know, a debt to the public markets and declaring bankruptcy. >> so donald trump spent almost ten minutes responding to the tax returns that were released in just one of his rallies today. here's a quick clip of what he said. >> i have often said on the campaign trail that i have a fiduciary responsibility to pay no more tax than is legally required like anybody else or put another way, to pay as little tax as legally possible. >> he went on, reid, to say he brilliantly used the tax laws. is there anything to that? >> well, i mean, he hires a

whole bunch of accountants, wealthy people can do things with net operating losses, you know, tax deduction, et cetera, things that are not available to your average american, you know, not available to the people who, you know, put in their, you know, eight hours a day of hard work and to say that's brilliant is not brilliant. nevertheless, the key point is losing nearly $1 billion actually, in fact, doesn't make you a very successful businessman and doesn't actually make you brilliant. >> so today's tax code is about 3,000 pages which is its own massive problem in and of itself. putting that aside for a moment, it's 3,000 pages so that to your point, accountants can read it and people can use whatever is legal to pay as little tax as they are legally required to pay. look, your company, linkedin, has been criticized, citizens for tax justice has criticized you for a similar situation to donald trump there a sense that the company ended up paying little to no taxes. different reason, obviously. i know it was stock option related. but i guess the question is, would it be irresponsible for donald trump to not take

advantage of tax breaks if they are legal, if they are in the irs code? >> well, so, obviously following the law and taking advantage of loopholes, you know, it makes sense to do that as an individual, as an individual trying to minimize your own tax burden. however, it's really awkward, almost indecent, to be claiming i am a great public servant, i want to serve you, and by the way, i go through enormous amounts of expense and energy to avoid contributing my fair share into the common coffers. it's not to say you can't do it, isn't to say it's legal, but it really actually, in fact, is not continent with the claim that i care about all of us, i care about contributing my fair share. that's the disconsonance. >> so you specifically offered, reid, to donate up to $5 million to veterans groups which trump has said is a cause near and dear to his heart. you're doing it in the form of a match. as we get closer to your

deadline womehich, of course s final debate october 19th, where do things stand right now? >> crowdpack has raised over $1.2 million from 11,000 people in all 50 states including some of those key states like ohio, florida, pennsylvania, because americans do care about openness and honesty and transparency in the taxes, so all it requires now is for trump to do the right thing. and essentially say, no, let me reveal my taxes, let me be open and transparent, let me actually be, you know, a partner with the american people so that they can see who i am and they can make an informed judgment. and then all of that money would flow to the various veterans organizations that was selected. >> thank withdrew veyou very mu. i appreciate it, reid. >> thank you. "outfront" next, jeanne moos with some of the great moments from "saturday night live's" trump/clinton showdown. >> picking up somebody's sniffing here. think it's her sniffs. she's been sniffing all night.

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the debate everyone was waiting for. no one corner, alec baldwin as

donald trump, in the other kate mckinnon as hillary clinton. when it came to separating the real from the fictitious, can you tell the difference? here's jeanne moos. >> reporter: from the donald's sniffle -- >> can you hear that? i'm speaking up. somebody's sniffing here. i think it's her sniffs. >> reporter: to the hillary shimmy. >> whew, okay. >> reporter: "snl's" debate was like the real one, but on steroids. the real donald kept interrupting. >> the invasion of iraq -- >> wrong. >> that is absolutely -- >> wrong. >> -- proved over and over again. >> wrong. >> he actually -- >> reporter: while alec baldwin in his debut as trump did more than just wrong hillary. >> unfit to be commander in chief. >> wrong. >> he is a bully. >> shut up. >> he's either not that rich -- >> wrong. >> not that charitable. >> wrong. >> or he's never paid taxes in his life. >> warmer. >> reporter: the reviews for alec baldwin's first ever trump impression were, in the donald's words --

>> the best. >> reporter: critics said baldwin was spot-on. perfect. totally nailed trump. on his show, "30 rock" he once tried to nail nixon. >> it's purgatory, tracy. >> richard nixon? >> reporter: kate mckinnon as hillary coughed her way on stage then paid homage to the late gene wilder as willy wonka. the real trump waited until after the debate to complain about his microphone. >> they also had, gave me a defective mike. did you notice that? >> reporter: the "snl" writers noticed. >> she broke it with obama, she and obama stole my microphone. they took it to kenya. they took my microphone to kenya. they broke it. now it's broken. >> secretary clinton, what do you think about that? >> i think i'm going to be president. >> reporter: "snl" picked some low-hanging fruit, mocking trump's pronunciation. >> they're going to jina. >> china. china. china. >> reporter: alec baldwin's trump was like a bull in a china

shop. >> it's pronounced jina. >> reporter: jeanne moos, cnn -- >> jina. >> reporter: -- new york. and thank you so much for joining us. we'll see you back here tomorrow night. "a.c. 360" starts now. and good evening, thanks for joining us. if you're looking for a week that could decide the election, get ready. if you're still reeling from last week, get ready for more. our breaking news tonight, new cnn polling that shows just how much ground donald trump, who's speaking shortly tonight in colorado, has actually lost since the debate a week ago. and that is only partially factoring saturday's "new york times" report he might have avoided paying income taxes for the last 18 years after declaring nearly $1 billion in business losses back in 199 5. he's been talking about it today. expected to talk about it again tonight. his surrogates have also been talking about trump and his taxes calling him a genius. hillary clinton certainly is talks about it as well, but using somewhat different terms. trump also spoke out an veters