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Don Lemon Tonight

Trump Caves On His Own Family Separation Policy; President Trump Slams McCain For Healthcare Vote Bloomberg To Spend $80 Million On The Midterms; Airlines Asked Federal Government Not To Fly Separated Children On Their Planes; American CEOs Call Out Trump's 'heartless, cruel' Border Policy; President Trump Says Melania Went Through A Pretty Big Thing. Aired 11-12a ET

Aired June 20, 2018 - 23:00   ET

THIS IS A RUSH TRANSCRIPT. THIS COPY MAY NOT BE IN ITS FINAL FORM AND MAY BE UPDATED.

[23:00:00]

DON LEMON, CNN TONIGHT NEWS SHOW HOST: This is "CNN Tonight." I'm Don Lemon. It is 11:00 p.m. here on the East Coast. Live with all the new developments for you right now.

President Trump caving on his own immigration policy, how own policy. After holding crying children hostage to gain political advantage. Only caving when there were too many heart breaking pictures to sweep under the rug, too many defenseless children begging for their mothers and fathers.

(BEGIN AUDIO CLIP)

(CHILDREN CRYING)

(END AUDIO CLIP)

LEMON: The President and his administration completely contradicting everything that they have told us about their own zero-tolerance policy. Their hands were not tied, as they claimed. They didn't have to wait for Congress to do something, and they can't blame the Democrats for a brutal policy that is 100 percent of their own making, but the fact remains more than 2,000 children have already been separated from their parents.

Some of them are being held thousands of miles from the border, and the administration can't really say whether the President's executive order will do anything at all for them. A mess.

I want to bring in now CNN political commentators, David Swerdlick of the Washington Post and Matt Lewis, for the Daily Beast, also CNN political commentator Dan Pfeifer, a former senior adviser to President Obama, his new book is "Yes we still can" in parenthesis, politics in the age of Obama, Twitter and Trump.

Thank you all for joining us and nice book cover. We'll talk about that. SO today the President said anybody with a heart would feel very strongly about this, but yesterday he said that you have to take away the children in order to prosecute the parents. Dan, what changed?

DAN PFEIFFER, CNN POLITICAL COMMENTATOR: The only thing I can imagine changed is the only thing that affects Trump. He saw bad television coverage about himself. There's nothing in Trump's history today, his presidency has only been a year and a half and it feels like 10 years that suggests that compassion or empathy is any sort of motivating factor to him. In a way he talks immigrant in his tweets today saying they're infesting the country, suggests that this is really a strategic retreat more than some sort of compassion move on his part.

LEMON: Matt, did somebody get to him? Do you think they were looking at polls and statistics and the feedback and the images and said, oh, this one maybe --

MATT LEWIS, CNN POLITICAL COMMENTATOR: I think he is right. It's the images. I don't think -- I mean who knows, right? Maybe there are really sophisticated in the polling and the focus group, but I think it is TV. You know, I think Donald Trump watches TV, and he makes decisions based on his gut, how he feels the narrative and story line is going. Maybe there are people doing sophisticated, you know, political analysis work. I don't think he would listen to them, I think it is worth on television and at some point he makes the call and then people scurry and they reverse engineer what they've been saying as recently as an hour earlier and have to find a way to make that jive with reality.

LEMON: David, remember though when the reporting was earlier in the week -- in the coming of the weekend as well, that the President was upset with the media, because he thought the media was cherry picking the images to make him look bad? Do you remember that? So --

DAVID SWERDLICK, CNN POLITICAL COMMENTATOR: Yes, Don, I do remember that. And I agree with Dan and Matt that the President wants this to look good for his image. And so when he thinks the images aren't showing him both simultaneously as a strong man and also as the benevolent daddy figure, he gets upset, because he wants to be seen as both of those things at the same time. What he has not appreciated in his year and a half as President, is that there are certain situations, this one being one, when you are talking about kids, where you can't be Robin Hood and the sheriff of Nottingham at the same time. You have to pick one. And he wanted both and when he realized as Dan said, that this one is going to be a loser for him, he made that strategic retreat.

Even though polls CNN SRS poll from earlier in the week showed that almost six in ten Republicans favored mishandling on immigration, in spite of two thirds of Americans overall disfavoring it. The bottom line is the President wants that good coverage. He wants to be seen as a hero, not as a cruel person even though he was implementing a cruel policy.

[23:05:12] LEMON: Yes. So, Dan, I want to take you to a rally tonight in Duluth, Minnesota, through the magic of television where the President really did focus much on immigration, but he did talk about the ways that he views himself and his critics. Here it is.

(BEGIN VIDEO CLIP)

DONALD TRUMP, PRESIDENT OF THE UNITED STATES: You ever notice they always call the other side, and they do this often, the elite, the elite. Why are they elite? I have a much better apartment than they do. I'm smarter than they are. I'm richer than they are. I became President and they didn't. And I'm representing the greatest, smartest most loyal, best people on earth. The deplorables --

(END VIDEO CLIP)

LEMON: So what's interesting is that that elite term is something that you use, you know, right as a buzzword. Was it created by conservatives -- his Party created that word elites. And now he is saying I'm above the elites. So what is he saying? Democrats, the media, Obama and people who support Obama and Hillary? Is that what he is saying?

PFEIFFER: I never know exactly what Donald Trump is saying, but it's worth noting that Donald Trump is an Ivy League educated billionaire by his own definition. We don't know for sure if (inaudible) tax returns, he is president of United States. I hate to break it to him, but he is one of these elites to which he so decries. But what it tells you is -- what Donald Trump -- some people are the heroes in the run stories. Everything they see, they see mostly hero.

Donald Trump sees himself as the victim. He does-- in every time it's why are these people mean to me, why are they picking on me? And it's just this deep, gnawing insecurity that fuels policy decisions, which is a very alarming way to think about how our government operates.

LEMON: It's interesting, because I wonder, -- I wish all of those people could see the circles that Trump fronts and very wealthy -- I'm sure they have an idea.

PFEIFFER: He has a gold toilet. He is elite.

LEMON: Yes.

LEWIS: But Don, you know, if you're going into a big game you want an elite quarterback. If you're going to the hospital you want that elite surgeon. The American people want this elite President.

LEMON: And he went to an elite school. Yes, you know, oh, well. American exceptionalism, I guess that doesn't matter anymore. So now listen, the President also blamed John McCain for the collapse of the health care repeal that they were trying to get done. He didn't mention him by name, but it was clear who he was referring to. Watch this.

(BEGIN VIDEO CLIP)

TRUMP: We had a gentleman late into the morning hours go thumbs down. That was not a good thing he did, that was not a good thing for our people, for our country, whether you're Democrat or Republican. And everybody said, oh, good, we have his vote, we have everybody's vote. We were going in for a routine repeal and replace, and he went thumbs down. Not nice.

(END VIDEO CLIP)

LEMON: So Jeff Zeleny is reporting tonight that one woman shouted out he is a war hero, and Megan McCain responded on Twitter tonight and she said, and it never stops being gross. Amen. Why does this President still feel the need to attack John McCain, a war hero, a long time public servant who is fighting for his life right now from brain cancer?

LEWIS: It's just, you know, petty, thin-skinned. And he becomes obsessed with things. Remember he was obsessed with the crowd size at the inauguration. He just couldn't let it go. I mean, the first time it was ridiculous, but months later he would bring it up. And I think this is similar, you know? That was a defeat. The health care bill, you know, failing to, you know, repeal and replace, that is a strike against his -- you know, against Donald Trump's mark and he can't let it go. Every things OK, they ended up passing tax reform. They got rid of the individual mandate. He can claim victory, but he can't let it go. And so not only does he attack as you mentioned a war hero, and the party standing bearer, not that many years ago, but also a guy, you know, battling brain cancer. It's totally unseemly, but it just shows you the childish behavior of Donald Trump.

LEMON: What do you think, David?

SWERDLICK: Yes. I think that is right. When you're only in it for your own aggrandizement, which all indications suggests that is a lot of what President, if not completely what President Trump has been about since he embarked on this, then it is hard to let go the idea that there is going to be people including those within your own party who sometimes are going to take a stand that goes against what you're trying to do, because they have their own political believes or they have their own constituency that they're trying to serve. And I think that is the case here with Senator McCain, right.

[23:10:10] Senator McCain, is a major political figure in his own right. Even though he is a Republican like the President, he doesn't have to agree with him on everything. Most politician and I don't want people, everybody out there on Twitter, you can spare me if I'm telling you, you know, that the President is inexperienced. I'm not saying it's an excuse. I'm simply saying someone who had been in the City Council, in the state legislator, in Congress, whatever before this would understand that sometimes you win some, sometimes you lose some. President Trump has only prior to being President been in zero- sum me, me, me situations. These idea that you're on a team sport now is foreign to him.

LEMON: Dan, let's talk about your new book. It is titled "Yes, we still can" and this your former boss, President Obama responded on these immigration crisis on Facebook, and a Facebook post on refugee, Dan. Here's what he wrote. He said whether our families crossed the Atlantic, the Pacific or the Rio Grande, we're only here because this country welcomed them in and taught them to be an American is about something more than what we look like, how like, how our last names sound or the way we worship.

You say yes, we still can, but I mean, who is going to lead the Democrats through all of this, if we still can?

PFEIFFER: We don't know yet who is going to be Democrats, but I wrote this book as to way to look at the Obama presidency, the prism of his battles against these forces that I think, ended up creating Trump. The rise of propaganda like Fox News, the birther conspiracy, the changes in media. And when I came looked at that, I think there are lessons Democrats can learn.

That if we do those things we can have a policy much more like Obama's than Trumpism. It's a conditional hope. Because it is not inevitable that we will get pass this moment, but if we can do it if we work and we think and we are smart about it. And I don't know who the right Democrat is, but people shouldn't listen to me. I was wrong about 2016. People should -- look at all the candidates. If 100 of them run, I hope they all run and let them go out there and make their case. And we will see the one who matters, we don't know what the -- elections is a matching of a person and a moment. We don't know what the moments is going to look like, so it's dumb to tell you who the person is right now.

LEMON: So, here -- I find interesting now, people usually talk to me about something that has happened in this administration. The biggest question I get now is so who's going to run? Who are the Democrats going to put up in 2020? Who do you think? Who do you think? I don't know. I mean --

PFEIFFER: In 2006 when they were thinking about who was going to run in 2008, no one mentioned Barack Obama's name two years before the election, they didn't think he would do it. And he end up in one on one, but everyone who asks me who's going to run in 2020, I say what do you do in 2018, because that is the election we need to win and we need to win it right now.

LEMON: Right. OK. I got to run, but I will tell you-- here's what they say next, do you think it'll be Bloomberg, do you think it'll be Biden? That is the next question. I don't know and then sometimes there is --

SWERDLICK: Don, the Democrat's strongest candidates are the women. Warren, Gellibrand and Harris.

LEMON: You think so?

SWERDLICK: I think so.

LEMON: You think they can win?

SWERDLICK: I'm not sure which one, but I think the Democratic women Senators are the strongest people on their best.

LEMON: I'm getting in time trouble. Here is the other thing that people say, all right, people are going to get mad, but that is why I am being honest. It has to be a man and it has to be a white man to beat Trump.

SWERDLICK: Disagree.

PFEIFFER: That is (inaudible).

LEMON: I hear that from all Democrats. I'm just saying. I am not saying that, but that is what I am hearing. Thank you. Stand by for his book, again it is called "Yes we can, politics in the age of Obama." -- "Yes, we still can.

PFEIFFER: You can find it.

LEMON: When we come back the President saying his wife Melania and daughter Ivanka feel very strongly about migrant families being separated at the border, but did they change the President's mind? ,

[23:15:00] (COMMERCIAL BREAK)

LEMON: President Trump doing a 180 today on his policy separating families at the border, but should some of the credit for that go to his wife, Melania? Maybe his daughter, Ivanka? I want to bring in now Emily Jane Fox, senior reporter for Vanity Fair, she is the author of Born Trump, inside America's first family, Born Trump inside of America's first family, Emily Jane Fox. Go out and buy this book.

EMILY JANE FOX, SENIOR REPORTER, VANITY FAIR: Please.

LEMON: I am really happy to have you back on the show.

FOX: Thank you.

LEMON: I am very anxious to talk about that and the book. Look, can we do some news of the day? I want to talk about the President and what we heard from him when he signed this executive order. Here it is.

(BEGIN VIDEO CLIP)

TRUMP: Ivanka feels very strongly, my wife feels very strongly about it. I feel very strongly about it. I think anybody with a heart would feel very strongly about it. We don't like to see families separated. At the same time we don't want people coming into our country illegally. These takes care of the problem.

(END VIDEO CLIP)

LEMON: Did Ivanka and/or Melania have anything to do with changing the policy? Should they get any credit for it or this is purely him.

FOX: I'm sure they did voice their opinions and it's hard to have any other opinion than this is horrible and this should stop right now, but I have to say Ivanka, according to reports from this network, sat down with her father yesterday to show him pictures. This is happening long before yesterday. The only difference was that Ivanka was catching heat yesterday and people were calling her out for not saying anything. So it's hard to give her credit for something she had weeks and weeks to sit down with her father to talk about and either chose not to or was ineffective in her talking to her father. So perhaps they may help him pushing it over the line, but there is so much political pressure on him, I tend to believe that that is what really, really got to change his mind.

LEMON: Yes. But they will -- no doubt want the P.R. for the good decision.

FOX: This is what happens every time. this is straight -- it's interesting that the first lady is now taking a little bit of the Ivanka strategy, but every single time there's a controversial issue somehow right when it's happening a story is out in the press and it's happened to me before in my reporting on Ivanka over the last three years, that she behind the scenes was lobbying for the better choice. And unfortunately, a lot of times that lobbying never pans out.

LEMON: Sometimes lobbying for the better choice means going in front of the microphones and saying I completely disagree with my father on this, or I'm working to change his mind or I am not going to stay.

FOX: I am not going to stay.

LEMON: Right.

FOX: How about that? That is really standing up for a core principle.

[23:20:0] So, it makes the question, is she there because she really believes she is effective and believe in something or is she there for another reason?

LEMON: Well, I think we know the answer to that. And the first lady, too, saying we're a nation of laws, but we also have to have a heart. It's kind of like, you know, it's having it both ways.

FOX: It is word salad.

LEMON: Yes. So, listen, he said another surprising -- speaking to the first lady, about -- he spoke about the surgery, last month, here it is.

(BEGIN VIDEO CLIP)

TRUMP: She is doing great. She went through a pretty big thing, but she came out -- I mean, she is really -- great doctors at Walter Reed Medical Center. She is doing fantastic. She is all 100 percent.

(END VIDEO CLIP)

LEMON: Sounds more serious than we had originally been told.

FOX: People who are closer to the first lady have expressed to me that perhaps we don't know the full picture, and this is something that is a hallmark of our first lady, that she is incredibly private. And what's interesting to me is that, it's been her husband who's spilled the beans on anything we know about her health. This is something she has kept very close to her closest friends, closest advisers, but her husband has been the one out there talking about it.

LEMON: I want to get in two things, make sure we get this quick if you can. Michael Cohen putting a statement out today basically going against what this administration did. How significant is that saying I can't stand for this zero-tolerance policy?

FOX: I don't know that we should read into it, anything related to his legal case, which I know is easy to do. Michael Cohen is going to resign from the RNC. From my reporting this is something he is basically been waiting to pull the trigger on for weeks if not months. And so, I think he was deeply impacted by these images as we all were. And so it was time for him to resign, and this was a good way to get some possibly good P.R. right now.

LEMON: OK. A little bit from your book and this is about Don Jr. You said, Donald Trump have never understood Don Jr. passion for hunting. He was certainly never going to share it, so when on the campaign trail then Governor Terry Branstad invited Donald to his state for a hunting trip, an activity that would appeal to the candidate's base, he sent Don Jr. in his stead. Don, you can finally do something useful for me, he told his son. That is pretty -- you can finally do something.

FOX: What every loving parent says to their child. It just speaks to the dynamic that he has with his children and really the way the President speaks to everybody. His children are not immune to the disparaging disrespectful way that he is speaking to people.

LEMON: Are they that close? I wonder how often they speak. Because remember during the separation and then divorce from Ivanka, they were estranged. It's no secret. How close were they?

FOX: Sure. You know, there was a fracture in the relationship after the divorce which happened when Don Jr. just turned 12 years old. And he was very angry with his father, he sort of rebelled, had a lost year and after he graduated from college he wasn't sure he wanted to go work for his father. But once he made a decision to go back and work in the Trump organization he was full in. And you saw him on the campaign trail nonstop. That was his whole thing for a year and a half.

LEMON: There's so much in here, I want to get one thing in. So Jared wanted to run the campaign? He didn't think Kellyanne Conway could do it?

FOX: So this is pre-Kellyanne Conway. There is a lot of people around him.

LEMON: People with experience.

FOX: None of them had any experience. This is the first time for everybody, but he is thought of by a lot of people as de facto campaign manager and knew it would be a good thing to get a woman in and then Kellyanne Conway appeared.

LEMON: What does that say about him?

FOX: It says that he has a lot of confidence in his ability to do things that he may have not have a lot of expertise in.

LEMON: Always a pleasure.

FOX: Thank you so much.

LEMON: isn't it so nice to be back on?

FOX: Oh, great. Lovely.

LEMON: Thank you. By the way the book is called Born Trump, inside America's first family, Emily Jane Fox, go out and buy and it is gold. That is very smart, that you did that with the book. The book is gold.

FOX: Thank you.

LEMON: I appreciate it. When we come back new video shows some of the young girls separated from their parents at the border are now right here in New York City along with over 200 other children. And the mayor had some pretty harsh words for President Trump about it.

[23:25:00] (COMMERCIAL BREAK)

LEMON: New York City's mayor finding out today that 239 children separated from their parents are being cared for at a facility right in the city. Now he is demanding that federal officials tell him how many more children may be here. CNN's Jason Carol has that story for us. Jason?

JASON CAROLL, CNN NATIONAL CORRESPONDENT: Well, Don, one city official says their priorities are trying to find out exactly how many of these children were sent from the border to New York City. And two, to try and get some sort of a plan from the federal government in terms of how to reunite these children with their families.

(BEGIN VIDEOTAPE)

CAROLL: Early Wednesday morning a camera captures a group of young girls entering an immigration foster agency in Harlem called the Cayuga Center. According to a federal source the girls were separate from their families after crossing the border. Now the City's mayor expressing outrage after his office has learned there are hundreds more just like them at this facility.

239 of them are right here right now. And this is just one of the centers in New York City. The folks here told us that since the program began over 350 children have been here. All because of the family separation policy of the Trump administration.

Mayor de Blasio says the youngest here is nine months old. Many are from Guatemala. At the facility they attend classes and receive social services during the day and go home with foster families at night. Workers telling the mayor some of the children had to be treated for lice, bedbugs and chickenpox. The mayor says some children need treatment for the mental trauma of being separated from their parents. And he is not convinced they will be reunited with their families anytime soon.

BILL DE BLASIO, NEW YORK CITY MAYOR: Well, we have to make sure they're reunited. I mean, this is -- this policy is so fundamentally broken to begin with. The kids are being sent thousands of miles away from their parents. We have to change the policy. We have to fight to change the policy.

[23:30:00]

CARROLL (on camera): Adding to the mayor's frustration, getting a sense of how many children were sent from the border to New York City. De Blasio's office said until today they had no idea 239 children were at this one facility.

(voice over): The city has six other immigration facilities where children could be held. The mayor says the federal government has instructed those facilities not to share information about children from the border coming through their doors.

Currently there are at least 16 states nationwide that have facilities for unaccompanied children, that according to an official list from Health and Human Services obtained by CNN.

New York's governor says the president's executive order ending separating families crossing the border does not address helping those 2,300 children who have already been separated from their families.

REP. ANDREW CUOMO (D), NEW YORK: This executive order is not going to do it, and using 2,000 children, pulling them out of the arms of their parents is as disgusting a process as I've ever seen. And it really says as a country, we should take a look in the mirror and are we still the United States of America?

CARROLL (on camera): So, Don, just a couple of points. The city still does not have clear numbers in terms of exactly how many children were sent from the border to the city. They are still waiting to gather that type of information. And two, they're still waiting for a plan from the federal government in terms of exactly how to reunite these children with their families.

The deputy mayor of Health and Human Services says tonight that so far, her office has received no instructions, no plan from the federal government in terms of how they are going to reunite these children with their families. Don?

(END VIDEOTAPE)

LEMON: Jason Carroll, thank you so much. When we come back, you've heard it again and again, the brutal separation of families at the border is un-American. It's not who we are. But history tells us a different story.

[23:35:00] (COMMERCIAL BREAK) LEMON: President Trump buckled today under intense pressure to put an end to the separation of families at the border. Critics insisting that taking children from their parents is un-American.

So joining me now to discuss is Michael Higginbotham. He is a professor at the University of Baltimore School of Law. He's also the author of "Ghosts of Jim Crow: Ending Racism in Post-Racial America." Also with me, Richard Reeves, professor at Annenberg School for Communication at the University of Southern California, who is author of "Infamy: The Shocking Story of the Japanese-American Internment in World War II."

I am so happy to have both of you, gentlemen, on to discuss this. So, a perfect panel of experts here. Michael, I'll begin with you. We've been covering these stories of families being separated, some in cages. We've heard some say that this isn't who we are as Americans, but history tells us a different story, doesn't it? Give us some examples.

MICHAEL HIGGINBOTHAM, PROFESSOR, UNIVERSITY OF BALTIMORE SCHOOL OF LAW: It does, Don. I mean, we have a long history of racial bias on immigration policies and practices of the country beginning with our first Congress in 1790, that passed a law that said only whites could be naturalized citizens.

And so Congress from then on embraced the racial hierarchy in our policies. It defined who was white as prohibiting Africans and Asians and American-Indians, but also prohibiting for a short period of time Southern Italians because they weren't white enough.

So there's this racial hierarchy that has existed in our policies and practices. It also exists in presidential enforcement. We've had President Hoover during the depression deported over a million Mexicans, many of whom were American citizens. It happened again in 1954, Operation Wetback it was called by Congress, and they deported another one million Mexicans, many of whom were American citizens.

So this has been going on for a long period of time. I thought it had changed, and I think many Americans look back at these practices as abhorrent and problematic. But it seems like President Trump has reaffirmed some of these practices with his recent approach on the border.

LEMON: So, Richard, to you now. The former first lady, Laura Bush, and others, have made comparisons to the Japanese interment camps seen during World War II. You wrote a book on it. What similarities or differences do you see here?

RICHARD REEVES, PROFESSOR, ANNENBERG SCHOOL FOR COMMUNICATION AT UNIVERSITY OF SOUTHERN CALIFORNIA: Well, the similarities, that our laws allow us to do pretty much whatever we want with both aliens (ph) and citizens. And 70 percent of 120,000 Japanese-Americans who were put in concentration camps, that was Franklin Delano Roosevelt's name for them, were because of public hysteria (ph).

Each time, the nation beginning back at the beginning, this was a nation founded by some very smart Anglo-Saxons, but it was built by wave after wave of immigrants from all over the world, whether it was Indians, Africans, Irish need not apply, anti-semitism. We have not accepted people who didn't seem to be like us until they were us. And they are us. It's the saving grace that we seem to be able to absorb the other.

[23:40:05] And if you're in Los Angeles, I think there is more other than us (ph). And this city couldn't run without them. The country couldn't run without them. We bring in immigrants for labor and then either when we don't need the labor or because they're different than us, go to different churches, speak different languages, we kind of try to push them out.

And that's what we were doing with the Japanese even though they were probably the most patriotic group in America. Seventy percent of those behind the machine guns and the searchlights were American citizens. And after 1924, orientals, both Chinese and Japanese, could not get American citizenship until the 1950s.

LEMON: You would think in 2018, that we would be beyond this way of thinking, Mike. I know that I had you both here for a history lesson and you're giving us good history lessons on Asians and African- Americans, on our Jewish brothers and this is on and on. But one would think by 2018, that we would not still be looking at this way, I don't mean everyone when I say we, but you understand what I'm saying.

REEVES: Well, I --

LEMON: That's for Michael. That's for Michael.

HIGGINBOTHAM: I do understand, Don, and I think it's a really important question because most Americans look back on those practices today and say they were wrong. This is about America's promise, not what we were, but what we are and what we can be. And we have been living up to that promise in some respects. But it seems like President Trump with many of the things he has done over the last year, it seems like he wants to take us back.

And, you know, I think about the Muslim ban. I think about his racist rhetoric with Charlottesville. But when I listen to those babies crying on the border, clearly something has gone wrong. And I think most Americans acknowledge that. And that's why President Trump blinked today with respect to what he tried to do.

LEMON: Well, let's hope the country's moved past that. But I've got to run. I'm out of time. Richard, thank you so much. We would love to have you back.

REEVES: Nice to be hear.

LEMON: Of course, Michael, thank you as well. Thank you, gentlemen. When we come back, Corporate America speaking out against President Trump's immigration policy as Michael Bloomberg launches a multi- million dollar plan to help Democrats in the midterms. Can he make a difference?

[23:45:00] (COMMERCIAL BREAK)0

LEMON: One of America's richest men reaching into his very deep pockets for the midterm elections to help Democrats take back the House. I want to bring in now William Cohan, a special correspondent for Vanity Fair who is a former Wall Street banker; CNN political analyst Alex Burns, national political reporter for The New York Times; and political analyst Molly Ball, national political correspondent for Time Magazine.

Welcome one and all. So, Alex, I'll start with you. Good evening, everybody. Your new piece out in The New York Times today, it is titled "Michael Bloomberg Will Spend $80 Million on the Midterms. His Goal: Flip the House for the Democrats." That cash will be a major boom for Democrats. So, what are your sources telling you?

ALEX BURNS, CNN POLITICAL ANALYST, NATIONAL POLITICAL REPORTER, NEW YORK TIMES: Look, this a really big deal and battle for control of the House. Republicans see the political environment against them. They feel dragged down by the president's unpopularity. They see this crisis at the border as just a total political fiasco for them.

But, the one thing they have felt they have had going for them so far is money, that they would be able to bring an enormous cash advantage in some of these really, really tight House races. Michael Bloomberg enters at this point with his enormous fortune, tens and tens of billions of dollars.

And for the first time, this is a guy who in the past has split his political spending between Democrats and Republican. He says he is going all in with one party and all in on one camp (ph). This is all about the House representatives.

LEMON: Well -- and we know that he is a real billionaire, because we have said -- I think you said in this program -- was that you that said there's no actual evidence that he --

BURNS: I have said that before, yes.

LEMON: So, there's no actual evidence that Donald Trump is a billionaire. We know that Michael Bloomberg is a billionaire.

BURNS: Plenty of evidence.

LEMON: Many times over.

BURNS: Absolutely.

LEMON: He does not like Donald Trump. Remember what he said at the convention in '16. Watch this.

(BEGIN VIDEO CLIP)

MICHAEL BLOOMBERG, FORMER NEW YORK CITY MAYOR, CEO, BLOOMBERG L.P.: Trump says he wants to run the nation like he's running his business. God help us.

(APPLAUSE)

BLOOMBERG: I'm a New Yorker, and I know a con when I see one.

(APPLAUSE)

BLOOMBERG: Together, let's elect a sane, competent person with international experience. A unifier who is mature enough to reach out for advice, to build consensus, and to recognize that we all have something to contribute.

(END VIDEO CLIP)

LEMON: That sounds like a declaration right there. So here's the thing. He is probably the fourth most admired billionaires of our time, Michael Bloomberg, right? Jeff Bezos, Bill Gates, Warren Buffet. He has made no secret -- none of them have made no secret of their contempt for this president. So, what does that tell you? Are you they going to be putting up all this money to go against this president?

WILLIAM COHAN, FORMER WALL STREET BANKER, SPECIAL CORRESPONDENT, THE VANITY FAIR: I hope they do. I think this is perhaps the first wave of it and it is nice that Michael Bloomberg is starting this early.

[23:50:01] He is putting a lot of money. I mean, $80 million sounds like a lot of money to me. It's obviously just a small fraction of his fortune, but I think it will make a big difference in getting Democrats elected I hope in the fall.

And if other billionaires want to join that party, I think it's great. I mean, I think CEOs are beginning to stand up for what's right in this country. It's long overdue. We can't allow this person who Michael Bloomberg described as a con man to hijack our country.

LEMON: What's interesting, though, is they are business people. Have made tons of money. He said, I know a con man when I see one. They know Donald Trump. They know him.

COHAN: And we know him, too. As New Yorkers, we know him. I mean, I think, look, here's the conflict that CEOs have. They like his tax law. They like some of his policies. They like the fact that corporate tax rate was lowered from 35 percent to 21 percent. That puts money in their pocket. It puts money in their shareholders' pocket. They like that.

But they don't like the high bait (ph) of president that he is. They don't like his immorality. They don't like his being out of control. They don't like the fact that it's 6:00 in the morning, he can sit the agenda for the day that makes everybody crazy.

CEOs need to know that they can count on a steady hand and so they can decide -- it takes a long time to decide to build plant and equipment and invest that kind of capital. You need to know a long time in advance that you are going to have a steady hand on the ship. And Donald Trump doesn't give anybody confidence.

LEMON: Yeah, they don't like his unpredictability, Molly, and probably going after personal companies, going after the NFL, going after Amazon and all of that, right?

MOLLY BALL, CNN POLITICAL ANALYST, NATIONAL POLITICAL CORRESPONDENT, TIME MAGAZINE: Yeah, but I mean, I do think that in general, Corporate America has been pretty happy with Trump. And I think that, you know, you see especially this sort of coastal elite billionaires like Bloomberg registering these kinds of objections. You're not hearing so much from, you know, proprietaries of say petroleum product company based in Wichita.

In general, they kept their mouth shut. They kept funding conservative causes if they were before. They're very happy with the tax legislation and they are not so bothered by some of the cultural stuff or they may even be wholeheartedly on board with it. So, you know, I don't think -- there have been defections from the Republican donor class.

There have -- we have seen a trickle of big name Republican donors actually come out and say, you know, for example, that they want to see the Republicans support immigration, for example. But it's a trickle. And I think for the most part, you do have a corporate class that's pretty much on board.

A steady hand, sure, they would like a steady hand. The next best thing to that is an administration that is more devoted to, you know, corporate tax cuts and deregulation than any we've seen.

COHAN: Can I interject something real quick? I'm a big fan of Molly Ball, but she is wrong about the Koch brothers who live in Wichita, have come out against Trump on his tariffs, and so there's some big Republican donors who are objecting, and they live in Wichita.

LEMON: I think she's speaking in general.

COHAN: No, I know.

LEMON: They're happy with tax policies that help --

COHAN: She's right.

LEMON: But what does this -- companies that rely on consumers, it's a bit different. Because if you look at -- look at what happened to businesses stepping forward today. American, United, Frontier, Southwest Airlines releasing statements asking government not to fly immigrant children separated from their families on airplanes and so on. You think it's different when it comes to companies that rely on consumers?

BURNS: Look, I think it's important to distinguish where individual CEOs and independently sort of activist companies get involved versus where companies with big consumer bases like Delta and American Airlines decide they need to stand up to the administration on something. It's not because they're pushing an ideological agenda. It's ultimately less about the corporation deciding to be political than it is about fearing their consumer base.

It's why a lot of the companies that have clashed with the administration, that haven't tried to sort of, you know, find accommodations or see themselves out of the fight have been companies with these sort of upscale relatively educated consumer bases that don't like the president or offended by his policies on things like immigration, on issues like transgender rights. The companies that are speaking out are mostly not just doing it out of the goodness of their hearts.

LEMON: Yeah. It's not just that, the tech world as well. Right? Silicon Valley. Look, leaders from there are calling out the immigration policy. Apple CEO Tim Cook says it was inhumane. Airbnb co-founder says it is immoral.

Microsoft described itself as dismayed and also clarified the company isn't working with the government on any project related to separating kids from their parents. Do you think that these companies are the last check maybe on the president's behavior, no?

[23:54:59] COHAN: I'm not so sure I believe that. I mean, I think this was a policy that can be universally condemned and has been. I noted today or was it yesterday when Lloyd Blankfein, the CEO of Goldman Sachs, spoke with the Economic Club of New York, he is more ambivalent on that.

LEMON: Yeah.

COHAN: But, you know, this is a guy who doesn't like to change his policies and doesn't like to admit that he loses. So I'm not sure he's going to give in to any pressure from anybody.

LEMON: I got 20 seconds, Molly. I'll give you the last word here.

BALL: Yeah, I mean, I think for Silicon Valley, it's not just about their customer base, it's also about their workforce, both the composition of their workforce and the politics of their workforce.

But I think they have to tread really carefully because a lot of people suspect that they are mostly coming into this issue not out of the goodness of their hearts but because they want more labor and they want more visas and that's their principle stake in immigration reform, not some grand moral statement.

So I think that the business community has to tread carefully on this issue lest it be perceived as merely out for its own interests.

LEMON: Thank you all. I appreciate it. That's it for us tonight. Thanks for watching. I'll see you right back here tomorrow.

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