Trump tries to regain his footing and as the vicepresident ss candidates get their big chance on the debate stage. This is a choice, men and women, are whether or not were going to continue to go downhill to a weaker america on the world stage. You cant spend your whole life hiring lawyers to evade paying taxes and then suddenly at age 70 say, boy, im going to be great for the vets. Been stiffering them all my life but im going to be great for the vets now. With us to share their reporting and insights, and from politico and cnn correspondents. Last week was a bad fweeshg donald truweek for donald trump. History, in 2012 donald trump posted this graphic on twitter. Half americans dont pay taxes despite crippling national debt. The suggestion, is there a lot of free loaders out there . Turns out donald trump may well be one of them. The New York Times obtained copies of one year of trumps state filings claim 1ds billion losses, in 1995. Because of that tax experts told the times he could have avoid paying federal income taxes nearly two decades. His campaign is threatening to sue the newspaper but surrogates tell you this is exactly why you should vote for trump. Theres no one whos shown more genius in their way to maneuver around the tax code and to rightfully use the laws to do thavgts the mans a genius. He knows how to operate the tax code for the benefit of the people hes serving. The mans a genius. Theres that old metaphor, making Chicken Salad out of but what but what are they going to say, i guess . The Trump Campaign, any indication hell decide, okay, heres the rest of my taxes put these in context . They dont deny authenticity but the New York Times obtained illegally, maybe well see you. The Hillary Clinton has a brand new ad out, turn it around, bring it you. Where its headed . Hes not going to release his tax returns i am willing to predict that. But look at whats the up side for him . Releasing his tax returns . Is he going to win a single voter over a single undecided voter over . And i think, though, that the bigger question for him as people begin to process this is, not even so much that he used the breaks that are available in the law, but that they were born of a gigantic business failure in the middle of the 1990s. The economy was booming, and somehow he managed to have that Chicken Salad moment with his businesses. His casinos losing money, airline a failure, had, the palace hotel and other Real Estate Investments went bad. It happens. Hes in a big business. Big Business Safety monis a lot. To your point ashes bad youre, you are a smart businessman he could prove he had good years by showing other years. Right . But he isnt going to do that or being a surrogate. No harder job in politics being a surrogate. Though only three of them. To glenns point, striking how a few members of congress or governors, he has out there, working for him and he literally has about half dozen surrogates. From prominent members of american politics. Huge gains. Those people, sitting members of congress invisible. Extraordinary. Filled by Newt Gingrich, Rudy Giuliani and chris christie, in in sways , in in sways s in sways ome ways iterations of donald trump. Saying the same thing and saying exactly what trump says about himself, that hes a genius. Say hes a genius. Very frustrating, not just for us, news organizations asking for clarity, context, explain the laws, what loopholes, deductions legally. No indications donald trump did anything illegal here but frustrating for republicans. A lot of candidates throughout for congress and senate and governor and they get asked about this stuff and when you talk to their campaigns they say, when they reach out to the Trump Campaign they get the same talking points. He took advantage, didnt do anything wrong. Took advantage of loopholes available and paid very little or nothing, that makes him smart. And most americans dont want to pay taxes anyway or pay as few as possible. Thats what donald trump was doing. The problem, theyll hear about this in television ads. Priorities usa cut an ad theyre playing in some of these battleground states. Featuring a woman in ohio where shes talking about donald trump playing by different rules. She had to pay taxes. Hes not supporting veterans, not is a importanting schools. Tough to get out of this and Hillary Clinton brought this up in that debate. This is going to continue to dog him. I think youre right. Hes not going release his taxes but more questions, who would you want as president and would he close loopholing allowing him to take advantage of this large tax writeoff in the early 90s . Apparently no if you look at his tax plan. They have him from both ends of the income scale. He stiffed the United States government. Their agent. Also an incredible weight of evidence that he stiffed vendors who worked for him. I thought that was actually one of the more powerful moments of the ho hoff tr hofstra debate. I have people write mere, stiffed, father owned an antique store, grabbed a 2,000 lamp and said, ill pay you later, only after several months he actually paid up. Something that contributes to a narrative of this guy stiffing people. Saying hes for the little guy and being a hypocrite and to the old tweet, sends out a tweet saying half of the americans why arent you paying taxes . In debt. Hillary clinton said, tim kaine, too, before you jump in, to your point about the surrogates. Talking points from the campaign, god bless them. We all want loyal supporters. Chris christie saying, people saying explain this loss . I thought he was a great businessman . Donald trumps calling card i will do for the government what i did for my business. Asking for details and you get this. This is actually a very, very good story for donald trump. You know, about the losses. The fact is that this is a guy who rebuilt his entire Business Empire after the recession in the early 1990s, wrote the art of the comeback. Let me tell you, America Needs a comeback and we need somebody like donald trump to lead that comeback. Again, an easy way to prove it. If theres a great comeback, lets see 1996, 1997, 1998, and so on and so forth, and you can prove the comeback story, but youre willing to bet, from the Washington Post, willing to boat steve bezos fortune . Willing to bet anybody elses but mine. Yeah. Again what is the upside to releasing his tax returns . Especially whats the upside five weeks before the election . Some indication since the debate, though, that Hillary Clinton is gaining nationally in polls and key swing states. Might they get to a point where they see this pressure . Why you see him this morning on the clip you played at the intoe to the show. Moving on now to the emails. Right . Moving on to living off the land territory where you reach for whatever message that day falls into your lap. Last week it was Bernie Sanders dissed by hillary on this hacked tapes and trying to find way to change the topic. One fast point, though, for hillary. If there is a sort of a cloud, a Silver Lining for her, she almost has to pick, because theres so much out there for her. Does she want to prosecute a populist case against donald trump and portray him as hurting the little guy . Getting way with stuff that average americans cant, or do you want to do what she has been doing. Much more gender and race and saying this guy is an outright lier in American Life in 2016 and this is going to set us back. Get a sense of that. In ohio, well get a sense of that. They say theyre going to, my words, channel an Elizabeth Warren and have a populist, after the epipen maker, wells fargo and donald trump as a businessman. Before you jump in what shes done on twitter. Tweets are priceless. Hillary clinton again trying to get under Donald Trumps skin as she did to a degree in the debate. Can man who lost a billion dollars in one year stiff Small Businesses to glenns point and paid no taxes maybe claiming hes good at business . And then says, again, i think this is designed to sort of goad trump into saying more. According to the New York Times, trump pay contribute more to our College Students and military than he wants to deport the undocumented immigrants. She goes after the very points about Donald Trumps biography he is most proud of and punctures them. I think that whoever they have on the campaign whos studying his psychological profile know that this is the single most guaranteed way to force him to erupt and you know, at 3 00 in the morning, thats what hes worried about. And they did that early in that first debate. Jit her second answer was about his wealth inherited from his father, 14 million. His daddys money. And from there pretty much off the rails. In some ways to jonathans point, its sort of all of the above. Go with the race stuff, gender stuff as well as puncture an idea a populist out for the little guy and even barack obama talks about this. He said in one of his speech, all of a sudden donald trump is for the little guy, but you couldnt rent a place in one of his condo buildings. You couldnt get on his golf course, which i think is a pretty powerful message here as they try to get older voters, millennial voters as well as some of those workingclass whites. This isnt just a matter of attacking Donald Trumps psyche. Hillary clinton understands this psychology herself. She is having a big kick over the last couple of days. She is doing unto him as others have done unto her for a lot of years. To karens point in 2007 i sat down with her before the election, the race, really took hold and she said to me, the blood sport aspect of running for the president is that they attack you on your strengths. And she spoke about that in a defensive way. What were seeing right now is her being able to flip that around and turn it on donald trump. Well see if, what happens. Which trump we get this week. See if we get a disciplined trump, campaigned about 3,472 times. Get a disciplined trump and then he sewed, up next to the countdown clock. And then he goes off script. Started out today, military Cyber Security event. Tone more somber and dismal. Well see what happened. Saw what happened sunday night. Pressure gets you in a president s campaign. Watching it play out. Donald trump stays perfect on the trail this week, an issue in the Vice President ial debate tomorrow night. Hillary clinton will bring it up again with new information on taxes in the next debate next sunday night and here you live in a swing state youre about to see this. Im Hillary Clinton and ai prove this message. You work hard. You pay your taxes. So why didnt donald trump pay his . He claims hes worth 10 billion. But a new report shows he may not have paid any federal taxes for almost 20 years. He didnt pay any federal income tax. If hes paid that makes him smart. If he thinks that makes him smart what does he think of you . How stupid are the people of the country . Im Hillary Clinton well, if youre a trump supporter you dont like that, but thats a powerful ad. Yep. You know, from that debate you felt like it was going to be an ad, when he said that makes me smart. Now youve got ammunition with the New York Times reporting, this october surprise that land right in the middle of a really bad tailspin for donald trump. Think about, a presence of mind to move off her talking point. That makes me smart and stop, excuse me. What did you just say . That not paying taxes makes you smart. I want the people of america to hear thatcan you imagine the impact if she had gotten offscript and gone after him . Im guessing shell try again. Her experience takes hold. From the lazio experience, infamous lew crossed the stage. I interviewed her in april about this, the key on a debate stage is not what you say. Its how you react, and in that moment, i didnt want to stop this guy from making the biggest mistake of his career. She has the same attitude in terms of treting point. Sit tight. Up next, donald trump getting more personal on the campaign trail . Part of his warmup for that big second debate . Stay with us. I just took new mucinex clear and cool. 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After his overnight twitter tirade against the former Miss Universe last week, top Trump Campaigners promised he would be more disciplined. Well see what happens this week. End 67 last week, trump wandered off the telly propertier quite regularly. Raised bill clin clintons impeempment and said this. Hillary clintons only loyaltisy to her financial contributors and to herself. I dont even think shes loyal to bill, if you want to know the truth. And, really, folks, really, why should she be. Right . Now his adviser say its all fair game because Hillary Clinton calls trump a sexist and misogynist, but many other republicans worry its a strategy certain to exacerbate trumps already deep problems with women voters. This might not help either. Dont you think a man who has this kind of economic genius is a lot better for the United States than a woman and the only thing shes produced is a lot of work for the fbi checking out her email jgs. That was Rudy Giuliani playing the role of archie bunker. I mean, were laughing about this, but theres a president ial election in 36 days. Yeah. And maybe thats not what he meant, but it kind of the tone a woman. This woman, how about, secretary clinton, or this, the democrat, or his opponent. Why does it have to be this woman . Because shes in their heads. Rudy, i am old enough, i had hair at the time i was covering it, to cover Rudy Giulianis almost race again Hillary Clinton in 2000. Hes clearly got a score to settle, but this is not the man you want out there discussing womens issues. You know, my moment of the week last week was when giuliani and Newt Gingrich on the same day were discussing womens body image issues having to do with the Miss Universe controversy. Again, it gets back to the fact that guy cant have anybody standing on the stage with him who doesnt directly reflect him. Im old enough to remember, too, and didnt Rudy Giuliani blink, choose not to run . Yeah. You had your chance. Had his chance. He didnt he didnt run. And these are the people rounding donald trump and talking to him about this campaign. Youve got roger stone, of course, too, who has all sorts of theories about the clintons marriage. And area 51. Yeah. And Newt Gingrich, Rudy Giuliani and donald trump between the