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Clinton Blasts Trump, Avoids E-Mail Controversy; Donald Trump Stumps in Cincinnati; Attorney General Loretta Lynch Announces Case Closed on Clinton Case; Trump Defends Controversial Tweets. Aired 11p- 12a ET

Aired July 6, 2016 - 23:00   ET



[23:00:13] DON LEMON, CNN HOST: Hillary Clinton spends the day on the campaign trail bashing Donald Trump, but it's what she doesn't say that's got a lot of people hot under the collar. This is CNN TONIGHT. I'm Don Lemon. Not a word about her e-mail scandal on the day the other shoe drops.

Attorney General Loretta Lynch declining to press charges. When will Clinton speak out? What will FBI Director James Comey say tomorrow on Capitol Hill? And what will all of this mean to voters?

Meanwhile Donald Trump doubles down, selling a crowd in Cincinnati that Saddam Hussein was good at killing terrorists. If you ever heard of Trump's speech, you've probably heard him say that. So, why are so many people outraged about it now? We're going to talk to a man who says that outrage comes straight from the Clinton campaign. And remember this, you'll hear Trump's explanation for this Clinton bashing tweet.

Let's get right to CNN's Sunlen Serfaty. She joins us now this evening. So, hello Sunlen. We heard a vintage Donald Trump tonight and he covered a lot of ground. What's he saying?

SUNLEN SERFATY, CNN CORRESPONDENT: Well Don, he said a little bit of everything tonight. This was somewhat rather of a stream of consciousness, I should say from Donald Trump tonight at his Cincinnati rally. And I think this is the exactly the sort of off- the-cuff comments and speech that gives Republicans still so much heartburn about Donald Trump. He really covered the gamut of so many topics, but there was a lighter moment, kind of odd moment I should describe it as when a mosquito flew in front of him. Well, here's his reaction.


DONALD TRUMP, (R), PRESUMPTIVE PRESIDENTIAL NOMINEE: The Democrats -- ooh, there was a mosquito. I don't want mosquitos around me. I don't like mosquitos. I don't like those mosquitos, I never did. OK, speaking of mosquitoes, hello, Hillary, how are you doing?

(END VIDEO CLIP) SERFATY: So certainly an impromptu moment there at the podium for Donald Trump really wasting no opportunity to turn it into a moment about Hillary Clinton, of course, red meat (ph) to that crowd, Don.

LEMON: Did Hillary Clinton reacted Trump's rally tonight?

SERFATY: Well, she didn't say anything at all. But I should say her Twitter account really said everything, in the middle of Trump's speech. The Hillary Clinton Twitter account tweeted out, quote, "Newly discovered footage that could destroy Donald Trump's campaign if everyone saw it," and it was a link to a live stream of Donald Trump's speech as he was continuing to speak. This is so unheard of to see one opponent tweeting out a link to a speech telling people to tune in to another, their rival's speech, so unheard of, clearly the Clinton campaign, Don, thinks that did him a load of harm tonight.

LEMON: And Trump also reacted to the attorney general's announcement that Hillary Clinton will not face charges. What did he say?

SERFATY: That's right. This is just giving him fresh political fodder, of course that he wasted no time bringing up at multiple times during his speech, really laying into Hillary Clinton, again, crippling down on his nickname for her Crooked Hillary, bringing up the impromptu meeting that Bill Clinton had last week with Loretta Lynch.

But he did also bring up the fact that there are been some speculation, some suggestion that Hillary Clinton could keep Loretta Lynch as attorney general if she were elected president. Here's what he had to say.


TRUIMP: The attorney general comes out and the attorney general says "No charges!" That's bribery, wouldn't you say? That's bribery. You're not suppose -- she said she's going to reappoint the attorney general and the attorney general is waiting to make a determination as to whether or not she's guilty and, boy, was that a fast determination. Wow. Should have waited. At least waited a little bit longer. Don't just come out with one or two sentences. Talk about it a little bit.


SERFATY: So Trump really bringing out a big and fully loaded word there, bribery, tonight, making clear that he is going to continue to lay into Hillary Clinton on this. I should note that Donald Trump will be up on Capitol Hill tomorrow meeting with Republicans and the FBI Director James Comey will also be there. He will be testifying between -- before the House Oversight Committee. Don?

LEMON: And miles to go before November. We've got a long ways. Thank you, Sunlen. Appreciate that.

Now, I want to bring in Dave Wiegle, political reporter for "The Washington Post". Yay, he's finally here. And CNN contributor Bakari Sellers and Hillary Clinton supporter. Good to have all -- both of you on. Bakari, first off, your reaction to the attorney general saying Hillary Clinton won't face any charges?

BAKARI SELLERS, HILLARY CLINTON SUPPORTER: Well I think the process had to run its course. You had the investigation by the FBI. That is the investigative body. It turns its investigation over to the prosecutorial agency and Loretta Lynch made her decision.

I heard you and many others questioning, you know, when was she going to speak. Well, there was not much to say until the attorney general actually rendered her decision. So I expect that she will actually address these issues and many more in the near future.

[23:05:06] LEMON: Do you want to talk about this, Dave, or can we move on and talk Trump?

DAVE WIEGLE, WASHINGTON POST POLITICAL REPORTER: Well, I think it was a mistake for the House Oversight Committee invite Comey on such short notice to talk to them. No offense to any member of the committee but if they had fours weeks perhaps to prepare a grilling for this guy, maybe they'd be prepared. Fro tomorrow, there's -- I think they're acting out a disbelief that they didn't get an indictment out of this and I don't think that's going to end well for them.

LEMON: Do you think they're overplaying their hand?

WIEGLE: Well, what they're trying to discredit in the way you saw Trump discredit the decision he made. There is a way to do that. I don't think getting lectured to or answered definitively by him on live T.V. tomorrow is going to be a way to do it. They could surprise but it hasn't gone well for them in the past on Benghazi. When is the last time you saw the House Oversight Committee nail the landing on something look this?

LEMON: All right, that's a good point. And let's talk Donald Trump now. He tried to clarify tonight something he said last night about Saddam Hussein. Here he is.


TRUMP: I wake up, I turn on the television, "Donald Trump loves Saddam Hussein. He loves Saddam Hussein." And I was just asked a question by the Cincinnati inquirer and said, "Mr. Trump, is it true that you love Saddam Hussein?" Essentially, like sort of that, you know. I said "That's not what I said." I said, "That's not what I said." So that's the narrative that goes around.

So I said, "Bad guy, really bad guy but he was good at one thing, he killed terrorists." Next day Donald Trump loves Saddam Hussein. I don't love Saddam Hussein. I hate Saddam Hussein but he was damn good at killing terrorists.


LEMON: So actually what he said yesterday was Saddam Hussein was good at killing terrorists. No one said that he Donald Trump loves Saddam Hussein. So playing to the crowd there, wasn't exactly the truth. So Dave, what's your reaction? Because your latest article focuses on how the media reacted to Trump praising Saddam Hussein for killing terrorists, even though this wasn't the first time he made these sorts of comments.

WIEGLE: As you said at the top, he's been saying this since late last year. And I've seen Jake Tapper several times ask him, do you really mean this? Yes, he really means. Yes, he really said it in front of Jeb Bush, yes he said it the debate where George H. W. Bush was watching, this is an argument he has made against the mainstream of the Republican party, kind of mainstream of Washington thinking, knowing that the American electorate, the Republican electorate certainly wants to relitigate the Iraq War and regrets that we went in the way we did.

Now, he's saying about Saddam Hussein is not actually correct. I mean someone he was aiding to Palestinian terror groups in the time we're talking about, he was killing rebels in his own country, there weren't necessarily -- actually all the people that he wants to think we're attacking us.

So it's not completely coherent. The way it turned into a campaign issue, though, is that this is -- he would think is a potent way to go after Hillary Clinton, who supported the Iraq War, who was driving force Libya intervention and the Clinton campaign turned it against him. And the way that I -- I want to see shake out because we in the media are not always that good at judging what goes over well with Donald Trump's electorate.

LEMON: What he's doing, Dave, is he's blaming the media. He's not -- you said ...

WIEGLE: Right.

LEMON: ... it's a good way to go after Hillary Clinton. But he's going after the media instead. Bakari, I mean, is that a good strategy? Shouldn't he be seizing on, as Dave said, Hillary Clinton rather than the media?

SELLERS: Well, I'm not -- I think Dave is actually the best follow on Twitter, but I'm not quite sure where he's going with this narrative.

UNIDENTIFIED MALE: High praise, thank you.

SELLERS: The fact is that Donald Trump was actually in favor of invading and going in the Iraq War before he was against it. So that has to be stated first.

LEMON: Hey, Bakari, before you finish ...


LEMON: ... I want to play because I think this is important. We just heard Donald Trump saying, you know, the media said I love Saddam Hussein, I love Saddam Hussein. This is what he actually said. Let's play then I'll let you finish it, Bakari. (BEGIN VIDEO CLIP)

TRUMP: Saddam Hussein was a bad guy, right? He was a bad guy, really bad guy. But you know what he did well? He killed terrorists. He did that so good. They didn't read him the rights, they didn't talk, they were a terrorist, it was over.


LEMON: All right. Bakari, continue. That's what he said.

SELLERS: Well, first, Donald Trump was for the Iraq War before he was against it. Second, Donald Trump didn't kill terrorists. Donald Trump killed tens of thousands of his own citizens. I mean Donald Trump, he even said, scud missiles ...

LEMON: Excuse me ...

SELLERS: Excuse me, Saddam Hussein sent missiles into Iraq and we just found out from recent tapes that Donald Trump even stated to some of his underlings, before he met his demise that he would send chemical weapons into Israel.

LEMON: Saddam Hussein.

SELLERS: Those are all -- Saddam Hussein. I keep giving this to Donald Trump. Saddam Hussein. I'm sorry. So those things are all facts. And the last thing we have to about this whole thing is that it just fits into this narrative.

[23:10:05] This isn't a narrative that Hillary Clinton somehow dug up. This is a narrative that it's a general election campaign. This is not Donald Trump debating Rick Santorum. This is the general election campaign. So, yes, people are paying attention to it and Saddam Hussein is not someone you need to be praising at any point.

LEMON: Dave, it's not just the media reacting, though. I mean Speaker Ryan distanced himself from Trump's commenting that Saddam Hussein was one of the most evil people of the 20th century.

WIEGLE: Yeah, I think the media has done a terrific job litigating this ,getting down Trump to explain what he meant. As Bakari pointed out, he flipped. He was for the Iraq War. He decided it was more politically advantageous to be anti-war, anti-intervention as soon as he became a candidate.

And the point I'm making is that I think the Clinton campaign has vulnerabilities. I talked to couple of Republican senators today trying to get an honest assessment of whether they think this hurts them now. This is before he did five more things that he embarrasses them.

But on this issue in particular, some of them said to me, well, it is a bit of a flip, a role reversal that the Democrats have a candidate who voted for interventions that are not very popular right now. Now, they're trying to justify things. People are very good at justifying things instead of looking into the best of what the Trump general election might look like. But that is how I heard them think about this issue. they weren't necessarily panicking about what Trump said just because the narrative last night and just because the Clinton campaign went into attack mode about it.

And when Trump says -- when Trump blames the media, it's amazing it's still potent but it remains potent. I think that's why he's so drunk on this kind of rhetoric because those crowd respond I think honestly into thinking anything that we say about him that makes him look bad, it's our fault, not his.

LEMON: But does that remain potent for the people who already, you know, or his supporters, for the people he needs, the independents and the people who may be on the fence, I mean does that really play? Because it seems so obvious that it sort of, you know, bait and switch, Bakari?

SELLERS: I mean, it is bait and switch because they went down this path of talking about some of Donald Trump's foreign policy, which is very, very shallow. I say it all the time. I mean, I hope they literally have a map at the foreign policy debate because I'm not sure he knows where Libya is, I'm not sure he knows where is Iraq is actually on the map.

But the fact is that Donald Trump was actually in favor of the Libya intervention before he was against it. Just like he was in favor of Iraq before he was against it. I mean, he's flip flopped so many different times. And what the media is doing, they're just shining a light on it. And even more importantly, I mean you can't change the fact that this is a new playing field. This is no longer 16 or 17 candidates talking about little hands and talking about all of these other things. These are the two heavyweights we have that are running for president of the United States.

So, yes, there's a new light that's being shown on it. And if Donald Trump wants to hammer on Hillary's e-mails and Hillary's e-mails, and Hillary's e-mails, that's one strategy. But if he wants to continue to get off message the way he's been doing the last two nights and squander those opportunities, then he have too deal with the ramifications there of.

LEMON: Yeah. Bakari, Dave, thank you. I appreciate it.


LEMON: We'll come back right. Donald Trump had a lot to say about Hillary Clinton tonight, a lot including accusing her a bribery. We're going to talk about that, next.


[23:16:49] LEMON: Donald Trump speaking to a cheering crowd in Cincinnati tonight and taking every chance to hammer Hillary Clinton. Here to discuss now is Alan Dershowitz, the author of " Taking the Stand: My Life in the Law " and also CNN Political Analyst Mr. David Gergen, a powerhouse here of knowledge.


DAVID GERGEN, CNN POLITICAL ANALYST: I deferred to him in all issues of criminal law. He was my criminal professor.

DERSHOWITZ: I take credit for everything he does.

LEMON: So then I'll give you the first question. I'll put in the hot seat. So Donald Trump said tonight, this was said by about Hillary Clinton and the attorney general of a decision not to press charges. Listen.


TRUMP: And Hillary then talks I think I'll reappoint the attorney general and you're waiting for a decision by the attorney general and you're saying you're going to give her a job. You're not allowed to do that. That's bribery, folks.


LEMON: So Alan, she hasn't said that she would reappoint Loretta Lynch as attorney general. But her not being charges. A lot of conservatives saying she's getting away with something.

DERSHOWITZ: Well I have to tell you, if she has said that she was going to appoint Lynch as attorney general, that would raise a serious question because it would put the thumb on the scale of her judgment, but she didn't say that obviously, and we have no idea whether she will, and Lynch doesn't have any idea whether she be reappointed or not.

Look, everyday and every part of he United States, people do acts that could be charged as crimes. Our criminal laws are so accordion like and elastic and discretion is always exercised. And this is a case where any responsible prosecutor, as Comey said, would have decided not to prosecutor. The real question is whether Comey should have gone further and made the statement he made and talked about all the other things. Also whether he should be the one making the decision whether to prosecute. Imagine if he were not the head of the FBI but a guy named J. Edgar Hoover. Would we want trust him to be the investigator, the person who applies the law and the person who uses the discretion.

So, we have to worry a little bit about empowering the FBI head too much.

LEMON: Are you going to agree or disagree with the distinguished professor here?

GERGEN: I agree and disagree.

LEMON: You agree and disagree.

UNIDENTIFIED MALE: How so? GERGEN: On the issue of Donald Trump and the charge of bribery, I

think that's ill founded and outrageous because there is no evidence. And I agree absolutely with Alan. Had she promised Loretta Lynch the job while this was under way, that would have been a scandal.

But I want to go back to the other point.

LEMON: Yeah go ahead.

GERGEN: And that is whether in Alan wrote a very interesting blog today on whether James Comey as FBI director, you know, played too abnormal a role whether (ph) for president, and he just raise a question about whether the FBI director should be deciding on what kind of charge might be brought. And I would just remind that it doesn't happen always and some doesn't happen publicly.

But in the Petraeus case the FBI made a recommendation to independent prosecutors that he be charged with a felony and then attorney general Eric Holder stepped in and said, no, we're going to make this a misdemeanor. So, it is not unprecedented. In fact, I think it happens fairly frequently that the FBI (inaudible) investigation will make a recommendation privately to the end of Petraeus case.

[23:20:11] LEMON: Would he -- would you said to me -- you said to me last night that these are two different cases.

DERSHOWITZ: Very different cases.

LEMON: The circumstances are different.

DERSHOWITZ: David makes a good point that there is that precedent. The big difference is that in this case Lynch had already announced that she wouldn't overrule the judgment of the head of the FBI.

LEMON: So meeting on the airplane ....


LEMOPN: ... with the former president.

DERSHOWITZ: Well, we don't know if closer relationship there but, presumably there is.

LEMON: Right.

DERSHOWITZ: And so therefore really was the FBI's judgment that was the final decision. But I agree with you they often make recommendation.

GERGEN: Sure. They make recommendation. I think no surprise because I saw Loretta Lynch said I'm going to go with the recommendation of the FBI and the independent prosecutors at the justice department. And so I wondered do you think she went a little early? Because the independent prosecutor just (inaudible) almost no time to review the evidence. DERSHOWITZ: And normally the decision is made realistically by the

head of the criminal division at the justice department, who is usually often a career prosecutor, very distinguished, very respected.

GERGEN: Do you think that person had sufficient time?


LEMON: Hadn't they been seeing the evidence in interviewing people over the time so it's seem like a short-time to us but -- the FBI not shared the information with the justice department.

DERSHOWITZ: That's what the FBI had said. He said nobody knows in the justice department what I'm going to say today. There must have been some sharing of information obviously, but there's some belief that maybe the whole justice department recused itself. That would be really unprecedend. That goes back to the Saturday night massacre.


LEMON: I want to play the speaker of the house today, his opinion on what happened. Here he is.


REP. PAUL RYAN (R-WI), HOUSE SPAKER: I was on the ticket in 2012. After the convention, you get the full declassified information as part of transition, as part of being a nominee. I think, the DNI, clapper, should deny Hillary Clinton access to classified information during this campaign given how she so recklessly handled classified information.


LEMON: Go, Mr. Dershowitz, what do you think?

DERSHOWITZ: One thing is clear, is she will never again be careless in the way she handles classified information. So if you're worried about the future, there is no one safer than Hillary Clinton today.

LEMON: Is that a grasp?

GERGEN: What do you mean by a grasp?

LEMON: something we have to find something that sticks?

GERGEN: Yeah, i do. I think it's -- they're trying to make up some argument she pay some penalty here.


GERGEN: But I think it's in the country's interest that both nominees get regular briefings here in the nomination. The world is incredibly complex. To Alan's point, she's not going to mishandle it. They come in and do verbal briefings for goodness sake.

LEMON: OK, let me ask you this. I have to get to a break. How many you've worked for how many administrations?


DERSHOWITZ: Since Grover Cleveland.

GERGEN: Yeah, right.

LEMON: So we'll say since Washington. It's a joke. Go ahead. How many administrations?


LEMON: Four. What would you advise Republicans to do on this?

GERGEN: I think the Republicans would be wise to have Donald Trump come down on the stump and leave it to the committees to do their work and keep the focus on Hillary Clinton and make sure that before this is over she answers questions in a responsible forum, whether be in front of journalists or in front the members of the Congress.

LEMON: Yeah.

GERGEN: But I don't think she can leave it here. She has not spoken on this issue in the 36 hours or so that it passed. I think that's a mistake

LEMON: OK. Stay with us. When we come back, we're going to continue this conversation. Don't go anywhere.


[23:27:35] LEMON: Case closed, at least what the Attorney General Loretta Lynch announced, announcing tonight that Hillary Clinton will not face charges for using a personal e-mail server. Back with me Alan Dershowitz and David Gergen.

So the FBI Director James Comey chooses words carefully, by the way, he's, you know, tomorrow he's going to have to meet with the folks up on Capitol Hill. He talked about the investigation. He said no reasonable prosecutor would bring such a case. So walk us through why that is important, Alan?

DERSHOWITZ: Well it's important that prosecutors exercise discretion all the time. A friend of mine wrote a book called "Three Felonies a Day" where she shows that the average American, you know, commits crime if you take the statute and use the broadest application. And you have to be sensible. And prosecutors exercise discretion. And when you have somebody who didn't lie to the FBI, when you have somebody who was, yes, very careless, but someone who was a patriot and someone who didn't intend to do any harm, normally a prosecutor won't bring that kind of case, especially when she's running for president of the United States. We don't want prosecutors and FBI agents to determine who our next president is.

LEMON: Yeah.

DERSHOWITZ: So you defer.

LEMON: There's this idea about being trustworthy and about lying but then there's also like what's classified and what's not classified? And that was a bit confusing yesterday in the press conference did have, as Alan and I talked about last night, the big classified stamp on it or was it something that just have classified information in it?

GERGEN: I think we're going to hearing perhaps a lot more about this tomorrow when Mr. Comey testifies and also when we hear from Mrs. Clinton as I assume I will. And that is that she said consistently I never seen -- received or sent an e-mail that was marked classified. And what the Comey investigation showed is there a 110 e-mails that she did received that contain classified information but it appears they weren't marked as classified. There were only two e-mails that were -- regardless (ph) confidential that were marked as classified.

So the question is, I mean, it sounds like hair splitting to a lot of people but is she hanging her case on the word marked ...

LEMON: Right.

GERGEN: ... whether they were actually marked or not.

LEMON: He went on to say any reasonable person, anyone in that position would have known, should have known that this information, that the e-mails contained classified.

DERSHOWITZ: That's not usually a basis for criminal charges. Now, you know, he did parse his language very carefully.

[23:30:00] He said they bore markings of classification. That's a little different than they were marked classified. I hope tomorrow we will actually see those documents, not the content, but just the metadata, that is -- was it marked classified or does it have indicia that it is classified inside the text.

GERGEN: Yeah. And I agree with that and I think it would be very, very helpful to see it. There is the additional argument that Comey would make though, that -- and it comes right out of the laws as you taught me is that, you are charged with understanding or having a knowledge, constructive knowledge of what you -- if you're the Secretary of State and you see something about drones, you know that by its very nature, it's classified. You don't have to have a big stamp on it.

DON LEMON, CNN: So then, did he stop just short yesterday of calling her a liar?

GERGEN: Yes. Yes.

LEMON: Go ahead, David.

GERGEN: He did stop just short of calling her -- I think he walked -- I think his view was that she walked up to the edge of the line and didn't go over and that's why he's not prosecuting.

LEMON: So was that a political decision or that is a legal decision, because people are saying it was political.

GERGEN: No, I don't think it was a political decision. I think they fought long and hard about it. I come into this biased. I think James Comey have been a straight shooter. He's one of the most honest men in Washington.

DERSHOWITZ: I agree completely, completely. And, you know, I think there's a big difference between lying, which is a big political issue ...

LEMON: Do you think he stopped just short of calling her a liar?

DERSHOWITZ: Yes. I think lying is a political issue, perjury is a legal issue. Perjury occurs in two ways. One if you do something under oath that's a lie. Second, a form for perjury is not call perjury is, if you lie to the FBI or to the Justice Department. And he said, quite clearly, she did not try to cover up.

LEMON: So he's going to be testifying on Capitol Hill tomorrow. He is going to be -- Comey. So, would do you think we're going to hear. This is going to be a political drubbing of James Comey or react she going to get something out of ...

GERGEN: Well, the Democrats have chance to ask questions too. But it's worth remember that James Comey testified back in 2007 in a case that was getting quite a lot of attention and he was superb and explain what he had done. And everybody looked at him, "My goodness, we didn't know how good he was."

DERSHOWITZ: And remember, the Republicans won't be well-prepared for this. They didn't take the time they need to do the kind of preparation that you need when you're going up against somebody who was as brilliant as experienced as Comey.

LEMON: So why rush? Why they rush?

DERSHOWITZ: Well, because they want to make sure it's today's news. This is all political clearly.

GERGEN: They want to do this before the convention. I think everybody got rushed by convention dates, including the FBI.

LEMON: So let me ask you, let me ask you this. So then, Loretta Lynch, the A.G., said today that it's over. She's not going to charge. Is there any way that Hillary Clinton can be charged with something?

DERSHOWITZ: Only if some new information comes up. On the basis of the current record, she will not be charged.

LEMON: It's over legally ...


LEMON: ... unless something else happens.

GERGEN: I want to ask Alan a question because I've been really ...

LEMON: Yes, sir. But they're telling me to tease. Go ahead.

GERGEN: The statute said you can be charged if you act with gross negligence. That's the phrase gross negligence. And Comey comes along and says, she was extremely careless and therefore not charging her.

To the lay audience, gross negligence and extremely careless, you know, - a distinction without a difference.

DERSHOWITZ: I agree with you. And that's why a digression is needed, because those terms are so accordionlike, you can fill it in so many different ways that you need a sensible prosecutor to look at the totality of the evidence and make a decision. Did she have the hamlet moment to commit a felony or not to commit a felony, that is the question and I think he was right to say she never had that moment.

LEMON: And, ladies and gentlemen, I have to say this. You've just seen a class, a legal class by Alan Dershowitz. I could go on longer but I have to go. Thank you, I appreciate it.

Up next, Donald Trump is not backing down, defending his campaign's controversial six-pointed star tweet. Wait till you hear how he explains it.


[23:37:55] LEMON: Tonight, Donald Trump not backing down his defending of controversial tweets sent out by his campaign. Here to discuss Republican Strategies, Kevin Madden, CNN Political Contributor Hilary Rosen, a Clinton supporter and Trump supporter Jason Osborne, a former Senior Communication Strategist for Ben Carson's campaign.

Kevin Madden, you first, Trump gave quite an interesting speech earlier in Cincinnati and he spoke about the Jewish star controversy. Let's listen.


TRUMP: So we have unbelievably dishonest media. So think of that, yes, so you have the star, which is fine, I should -- you shouldn't have taken it down. You know, they took the star down. I said, "Too bad. You should have left it there." I would have rather defended it, just leave it up and say, "No, that's not a Star of David. It's just a star. And it's also about corrupt Hillary, corrupt Hillary. But she sent it out. She said, "Oh, this stuff." She is the one that started the dialogue.


LEMON: OK. Kevin, what do you think of that moment?

KEVIN MADDEN, REPUBLICAN STRATEGIES: Well, look, I mean I think this is day 3 of talking about a tweet and think when you're 11 days away from your convention and you're 100-plus days away from the general election, you shouldn't be sitting on stage in a battleground state like Ohio that right, if you look at the polls, are dead locked talking about a tweet, relitigating what was in that tweet. Instead, you should be talking about the issues and anxieties that people have about the economy, about national security.

Donald Trump spends way too much time, in my opinion, talking about himself and relitigating some of these grievances he has with the media, which don't really speak to a lot of the anxieties and the anger that a lot of folks have about other things that really matter to them. That's one of the big problems with this as far as a tactical message and a strategy for the Trump campaign.

LEMON: So, Kevin, you are a Republican, a conservative, right? You're not a Hillary Clinton supporter, right?

MADDEN: That's right. That's right.

LEMON: OK. So I'm saying that because all of people who if you point that out as a journalist and they say, "You're supporting Hillary Clinton." You say, "No, I'm just pointing out the obvious that Donald Trump had a real opportunity to hit Hillary Clinton on the FBI, on what James Comey said."

[23:40:00] Instead, he is continuing to talk about a tweet and forcing news outlets to discuss and have this conversation as Kevin Madden, a conservative Republican just said.

MADDEN: Yeah. I'm a conservative Republican who wants to see conservative Republicans policies advance in this country. One of the things that I owe it to the viewers is to offer a clinical assessment of how some of those efforts are potentially held back by a candidate who focuses on things like tweets and what's in a tweet and then grievances that they have with the media.

Look, media bias is a fact. I actually believe that as well, but it is not a compelling message to a family in Columbus, Ohio right now that is struggling to pay their bills or worried about their mortgage, worried about other issues like higher education, the cost of higher education, the cost of health care.

That, that's the central part of what the message should be when you're the nominee of a major presidential party, when you're a presidential nominee and you're trying to make your case for the general election.

LEMON: OK. So, you know, he's in a battleground state, right?

MADDEN: Right.

LEMON: Tonight, Jason, he's in a battleground state. He's got the mic. He's got the podium. He can take it in any direction he wants to take it. Instead he took it in that direction. What do you think of that? What do you think of what Kevin said?

JASON OSBORNE, TRUMP SUPPORTER: Well, I understand what Kevin's saying and, you know, I tend to agree with him on some of that actually. I think we are spending too much time talking about things that are overblown in my view from the tweet. It's -- there was no intent, I don't think he's that kind of person. He does need to start talking and hitting Hillary a little bit more on , you know, what's happened over the last two days.

But at the same time, I do think, you know, that was one part of a very long rally today in Ohio where he touched on a number of different things. And I think one thing that I certainly saw working for Dr. Carson was the way that he is speaking and talking about these issues is the way that people are communicating them to the candidates in person in these states.

And so, I think he is demonstrating, you know, look, you're going to hear a lot of attacks about me. He's not the traditional politician that's going to speak in a set pattern that we're so used to over the last, you know, 200 years.

LEMON: Jason, all right, look, I don't want to, you know, be so negative but ...

OSBORNE: That's OK, go ahead.

LEMON: OK. So when you -- let's just do the comparison here. When you look at Hillary Clinton today, she's out there, she's on message. She's hitting Donald Trump one thing after the other, after the other on his business policy. She's very focused.

And then you have to come on and you have to say every time he's not a traditional politician. He's not -- Instead of saying, well, he hit her on this, he did that. He wasn't focused.

Tonight, his speech was rambling. He talked about so many things that there isn't one thing that you can focus on to -- you can take Hillary Clinton's speech today and do a complete assessment and say here is where she hit Donald Trump. If you take Donald Trump today, you cannot say here is where Donald Trump hit Hillary Clinton.

There are 25 things that he discussed tonight and I'm not sure that people who are watching, who may have been interested in his message may have not gotten anything out of it.

OSBORNE: But why is this a surprise? I mean, this has been going on for over a year now and he was actually when it came down to the ...

LEMON: You're not making a case for your candidate when you say why is this a surprise?

OSBORNE: But you're acting surprised that he is not as polished as a Hillary Clinton ...

LEMON: No, no, no. I'm not acting surprised. What I'm saying to you is, is that if everyone is saying, people like Kevin, people who are in the party, people like the Speaker of the House who are saying he needs to pivot, be more focused and be a more disciplined candidate, why is that not happening? So to make a long story short, his message did not appear to be disciplined today. OSBORNE: Disciplined for folks that are used to discipline candidates. I mean, this is a guy that won more votes than any other candidates in the Republican primary system ever, and he's been successful.

MADDEN: Yeah. But he's also -- look, it's called message discipline for a reason, Jason, and he's also, right now, losing to somebody who has historically high unfavorables, and has problems with honesty and trustworthiness and he's losing to her.

OSBORNE: Well, he's not. I think if you look at any polls. I mean, you're showing ...


OSBORNE: I'm sorry?

LEMON: What did you say, Kevin, at the end?

MADDEN: I'm saying he's losing to somebody who has a dramatically high unfavorability ratings because of his lack of message discipline and lack of focus on some of the issues that are really going to matter and bring him that last persuadable sliver of the electorate that he's not reaching.

[23:45:06] LEMON: So he's missing an opportunity to really take her on ...


... and he's missing an opportunity to focus on the issue, as you say, which is why you're here to talk about the issues. That's it.

HILARY ROSEN, CNN POLITICAL CONTRIBUTOR: So typically when two Republicans are fighting over Donald Trump, I would step back and keep my mouth shut but I'd just offer something on this table which is that, you know, Donald Trump is missing something that Hillary Clinton has, which is a real prescription for progressive growth in this country, for jobs, for infrastructure, for investment in education.

And his sort of asymmetric warfare that he engages in on an ongoing basis, whether it's an attack here, an attack there, occasionally he lands punches and all the Republicans say, "Yay, yay, that's the Donald Trump we want, the one who really hits Hillary hard."

You know, but really I think what voters are looking forgets back a little bit to what Kevin said, which is voters actually like the fact that Hillary Clinton has really detailed policy prescriptions. You know, the fact that she's kind of wonky on the stump doesn't hurt her. It means, she's extremely focused on those policies and when she does hit Donald Trump, she doesn't do the personal kind of attacks the way that he does, calling him a liar and crooked and all that stuff or for his 450 lawsuits that are pending against him.

What she says is ...

LEMON: She does hit him hard. She's been hitting him hard lately. Come on.

ROSEN: But she hits him on substance. You know, he bankrupted four companies and put hundreds of people out of work and small businesses didn't get paid. So she relates his problems to the kind of president he will be.

LEMON: OK. To that point we're going to discuss more of her message today in Atlantic City and we'll discuss it right after this. Don't go anywhere.


[23:50:53] LEMON: OK, Hillary Clinton hitting Donald Trump on his business dealings in Atlantic City, back with me, Kevin Madden, Hilary Rosen and Jason Osborne.

To your point that you were saying before the break, she was speaking in front of an abandoned remains of a Trump Plaza Hotel and Casino in Atlantic City, New Jersey. Clinton took Trump to task over his past business dealings in Atlantic City. Listen to this.


HILLARY CLINTON, (D) PRESUMPTIVE PRESIDENTIAL NOMINEE: When this casino collapsed because of how badly he managed it, hundreds of people lost their jobs, shareholders were wiped out, lenders lost money, contractors, many of them small businesses, took heavy losses and many themselves went bust.

But Donald Trump, he walked away with millions. That says everything you need to know about Donald Trump. It is not about what he can build. It is about how much he can take.


LEMON: OK. So, Jason, help me help you here. So this is, OK, a singular message today, a focus on Donald Trump's business dealings whether she is right or wrong. I'm not saying she is right or wrong on that.

ROSEN: Well, it's fact based.

LEMON: OK. But, listen, we'll get to that. But that is her strategy, one single message in the speech today. People can absorb it. They get it and then they digest it and they make of it what they will. Do you understand that?

OSBORNE: OK, of course I understand, Don.

LEMON: OK, go ahead.

OSBORNE: No. So I mean, I think to your point, I think what you're trying to say is that, Donald Trump is a rambling, you know, guy who doesn't have any clue about what he is doing.

LEMON: No, no, no. That's not what I'm saying. That's not what I'm saying. I'm saying what Republicans have been saying. I'm only saying that because Republicans have been saying, they wanted him to be disciplined, focused, pivot, in order to help the strategy on the right and to win the election. That's it, I'm not making a judgment on Donald Trump.

OSBORNE: Right. And I think, again, I mean, the idea that Donald Trump is going to be this polished politician is exactly why he, you know, has been so successful so far, that he is not.

He is somebody that actually speaks the kind of language in many cases that a lot of Americans speak, certainly, 15 million Republicans did during the primary season. And I think, you know, as campaign consultant, do you want your candidate to be, you know, to highlight one, two, or three issues at each speech, absolutely.

But at the same time, we've never experienced somebody like this that has clearly attracted, a vast number of people out there to support him because he understands or talks the way they talk around the kitchen table or at the barbecue on the weekends.

LEMON: OK. Kevin, I mean, you've been a strategist for the campaign. And to his point, I mean, he has gotten him this far.

MADDEN: Yeah. Look, it's not about polish. It's about credibility. And I think one of the things that the Trump campaign should do is demolish the credibility that Hillary Clinton is trying to gain on the economic issues.

First of all, you go back to the polling, this goes to a point that Hillary was saying before, if you ask people right now, where they stand, who they think would do a better job on the economy. Folks are actually siding with Donald Trump, why, because Hillary Clinton doesn't have a level of relatability.

You're asking somebody to say they want to lead an economy or relate to the struggles that average people have in today's economy when she hasn't driven a car in this century.

So those are the type of things that Donald Trump has to exploit. And I think what they're trying -- what the Hillary Clinton campaign is trying to do now is sort of demolish this pipeline to the economic populism that Donald Trump is a regular guy. And is potentially effective if Donald Trump doesn't go out there and fight back on these issues, and start to drive home the fact that Hillary Clinton doesn't have some of the right policies or doesn't have the right approach for average working Americans who worry about some of the things that they have related to the cost of living, the high tax burden that they pay.

That 's where they argument has to be focused. Not on the tweets, not on running a campaign on media bias.

LEMON: You have to admit, Hilary, that that would be a successful strategy because especially in the wake of what happened, you know, with Bill Clinton on the airplane, the former president, out of touch. Hillary Clinton hasn't driven a car, out of touch. You know ...

[23:55:02] ROSEN: I'm sorry. Do we think Donald Trump ...

LEMON: But no -- that that would be a successful strategy rather you agree with it or not. Don't you think?

ROSEN: Donald Trump analysis for how he integrates people is his elite Palm Beach club. I mean, come on. Do you think he has driven a car in the last 15 years?

So I think if we go through who is more out of touch with how real people live, that is going to be a ridiculous analysis because there's no question that the roots of Hillary Clinton and her middle class roots, you know, compared to Donald Trump being born with his, you know, silver spoon.

MADDEN: Why then, Hilary, do you think that she is losing on those issues right now, on some of the economic issues.

ROSEN: I don't think she is losing but I do agree if there is one place where Trump will appeal to middle class voters, it is a perception that he has some business skills he can bring to the country which is why it is so important for Hillary Clinton to continue to educate people and her surrogates on the fact that he is actually never been for the little guy. That he's always taken and not given that when he's had an opportunity to bring people up, what he's done is taken his own money and left everyone else high and dry.

So those are -- but those are the issues that people care about.

LEMON: We'll continue -- we'll going to have to continue this in another show. Jason, I wanted to give you the last word but Hilary, take your time. So I have to go.

MADDEN: Filibuster, Democratic filibuster.

LEMON: Thank you, everyone. That's it for -- I'll see you right back here tomorrow night. Thanks for watching.