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Rudy Giuliani Hot-Tempered When Someone Attacks His Boss; Whistleblower Complaint About President Trump Involves Ukraine; Trudeau Says He Does Not Know How Many Times He Has Worn Blackface In His Life; Democratic Donor, Ed Buck Faces Federal Charge For Allegedly Providing Lethal Dose Of Meth. Aired 11p-12a ET

Aired September 19, 2019 - 23:00   ET



DON LEMON, CNN HOST: And Attorney General Bill Barr under fire for advising the acting DNI not to share the whistleblower's complaint. Is he asking like the president's personal attorney instead of the chief law enforcement of the United States? We're going to talk about that.

Also, Justin Trudeau's growing blackface scandal. The Canadian prime minister now saying he does not know how many times he's worn blackface in his life.

And worthy Democratic donor Ed Buck facing a federal charge for allegedly providing meth to a young man who died of an overdose. We'll get into all of that this hour.

But let's get to our breaking news right now. CNN's Kaitlan Collins and Evan Perez join me from Washington. Good evening to both of you. Evan, there are a lot of new developments tonight on this whistleblower story. Take us through the latest reporting please.

EVAN PEREZ, CNN SENIOR JUSTICE CORRESPONDENT: Well, Don, the biggest new information comes from the Washington Post, which is reporting that whatever it was that really raised concerns for this allege whistleblower to come forward to the inspector general had to do with some communication, some events that had to do with Ukraine.

And of course, one, at least part of this appeared to be some communication involving the president. So, at this point we still don't know a lot of great detail about exactly the details of what exactly raised these concerns. What did the president say? What were these communications that were going on with this foreign leader?

But we now know that at least it had to do with Ukraine. And we separately also know that, you know, we know that the Trump administration has been holding up until recently about $250 million in aid. And so that's one of the things that questions of being raised about the timing of all this.

You know that the president spoke to the president of Ukraine in late July. And this whistleblower comes forward on August 12. So, again the timing here is a very big concern and one of the reasons why there's so many questions that still remain. LEMON: Evan, I got another question for you. Rudy Giuliani was on CNN

just a short time ago. What did he say about the president speaking with Ukraine's president?

PEREZ: Well, that's right. One of the big questions that remains is exactly what went on in that conversation. We know there was read out of the conversation that the White House put out. But what else might have been said perhaps that is what has caused this whistleblower to come forward.

Take a listen to what Rudy Giuliani said. Whatever was said in this conversation between the two presidents.


CHRIS CUOMO, CNN HOST: Will you finally answer my question now that we're 12 minutes in? Did the president --


RUDY GIULIANI, PRESIDENT TRUMP'S LAWYER: Do we really believe -- do we really believe he didn't know his son was under investigation?

CUOMO: Why don't you answer the question?

GIULIANI: What's the question? What's the question?

CUOMO: Thank you. Did the president talk to the Ukrainian president about what he wanted done with Joe Biden and what he wanted done with Paul Manafort?

GIULIANI: I have no idea, I never asked him that, I don't know if he did and I wouldn't care if he did. He had every right to do it as president of the United States. He had every right to say to the Ukrainian president, we have two outstanding allegations of massive corruption --


CUOMO: Did he asked you to do what you were doing?

GIULIANI: No, I did what I did on my own and then I told him about it afterwards --

CUOMO: Really?

GIULIANI: -- because I'm his lawyer.


PEREZ: And Don, that's one of the big questions that arises from this is, was the president -- was the president asking essentially for help from the Ukraine -- from the Ukrainian government perhaps to damage the Biden presidential campaign come 2020. We don't know. Obviously, that's what's the big thing that overhangs. And what Rudy Giuliani is avoiding answering in his answer to Chris Cuomo in the last hour. LEMON: Yes. So Kaitlan, we do know that there was a call between

President Trump and Ukraine's president. But we don't know if that is what's involved in this promise. Right? That's being reported. But there are interesting differences in the read out between Ukraine version and the White House version. What's going on here?

KAITLAN COLLINS, CNN WHITE HOUSE CORRESPONDENT: Yes, big differences. And we're not sure how Ukraine fits into this allegation. But if you look at the last time that the president that we know of spoke with the Ukrainian president we got two very different read outs from the White House and from Ukraine.

In Ukraine's read out it says, that the president was, quote, convinced the new Ukrainian government will be able to quickly improve the image of Ukraine, complete investigation of corruption issues which inhibited the interaction between Ukraine and the U.S.

Now we should note that the White House version was much shorter and didn't make any mention of that. Instead only talking about improving the relationship between the United States and Ukraine.

And while we're still figuring out how they fit into this allegation we should note that because of statements like this because of what Rudy Giuliani and the president's allies have been saying, there were already questions about the president's interactions with Ukraine long before this whistleblower's complaint.

LEMON: Kaitlan, nothing new from the president about this latest reporting but he addressed his whistleblower complaint on Twitter this morning.

COLLINS: Yes. It took him a little bit longer than we expected it would. But the president pushed back on Twitter, essentially saying that this is his style and how he communicates with world leaders.


He said that it's a fake news stories that it never ends. He said, every time he speaks on the phone to a foreign leader, he says, I quote, "I understand there may be many people listening from various U.S. agencies not to mention those from that country itself. No problem."

He said that "Knowing all of this is anybody dumb enough to believe I would say something inappropriate with a foreign leader along such a potentially heavily populated call? I would only do what is right anyway and only what is good for the USA."

But Don, we should note that, yes, typically when the president does make a call with a foreign leader it starts out in the situation room then the leaders are patched together on a secure line.

But with President Trump in office, he's developed this habit, sources have told me, where essentially, he will give out his personal cell phone number to some of his leaders that he's developed a personal relationship with. And sometimes he calls them at night when he's back in the residence.

There's not a lot of staff around. And it's not on that secure line. It's typically done through the president's cell phone not through the situation. So, there are instances where there aren't a lot of people on the president's calls.

LEMON: Boy. Thank you, both. I appreciate it.

Let's bring in Asha Rangappa, Juliette Kayyem, and Matthew Rosenberg.

Good evening. You heard all of that. You guys heard all of that. So, let's discuss now. Juliette, the Washington Post reporting that Rudy Giuliani's interview raised a lot of questions about the president's and the White House's interaction with Ukraine. Give me your take away, please.

JULIETTE KAYYEM, CNN NATIONAL SECURITY ANALYST: I think we're sort of missing the take away. Rudy Giuliani is Rudy Giuliani. I think my take away from today was another letter that the I.G. for the ODNI sent to Congress. And in that letter, it then becomes clear that this is not some, you know, Trump just trying to get policy change.

In that letter that was disclosed today the I.G. again says that this is an issue of grave concern which we should interpret tot being it is not a policy issue; it is not just someone who heard something passing in the hallway. But then adds this piece. Which is, it is also something that most significant and important of the ODNI's duty.

In other words, it relates to sort of American democracy. And the ability, if it is the Ukraine, the ability of our elections to be free and pristine from foreign influence.

And so, I think that letter along with the Washington Post reporting I'm tying it to the Ukraine. It suggests that this cuts to the core of our Democratic process and is not going away for the White House no matter how much they release election security funding or anything that they're going to do in the next couple days to try to get ahead of this story.

LEMON: Listen, Asha, a lot of people asking does the president have a right, the president have the right. Listen, he has a lot of leeway when it comes to dealing with foreign leaders, there's no doubt.

But you point out that his article two powers don't extend to offering quid pro quo. And if this it true then this is an abuse of power. Is it?

ASHA RANGAPPA, CNN LEGAL & NATIONAL SECURITY ANALYST: Absolutely. He can't use his article two powers for personal gain. And, you know, if there ends up being any indication that he offered something which is in his presidential authority in order to receive something that would benefit him personally, for example, in election. Then that is a problem.

There's a reason that the framers of the Constitution included bribery as an impeachable defense. They didn't want self-dealing. But, Don, here's the other thing. We literally just finished an

investigation about foreign interference in an election.

LEMON: Right.

RANGAPPA: Like, hello? OK. And what -- and you know, what ends --

KAYYEM: What was it called? What was it called?

RANGAPPA: It started with an M.

LEMON: Mueller.

RANGAPPA: The Mueller report as my daughter calls it. But you know, here, if there was the quid pro quo, if this foreign government is essentially digging up dirt that's going to help him, it is a thing of value.

LEMON: Right.

RANGAPPA: And the value is, you know, whatever aid or whatever he's willing to give that is an election, a federal election campaign violation. Which we've already been through. We've done this.

LEMON: But also found out that even if the president has committed crimes, then he can't -- may not be prosecuted for this. But it is troubling. I don't know, I'm not an attorney, but --

RANGAPPA: And I'll just add here, Don, is that, you know, in the Mueller report one of the big factors that the campaign finance violations weren't able to do prosecuted is a lack of knowledge on the part of the participants. That they didn't understand it.

LEMON: That's not --

RANGAPPA: That's not the case anymore.

LEMON: That's not the case. OK. So listen, Matthew, you have some new reporting I understand tonight from the New York Times. What can you tell us about it?

MATTHEW ROSENBERG, CNN NATIONAL SECURITY ANALYST: Look, this is set up basically, you know, sorry, excuse me, we understand that, you know, this was -- this was multiple, multitude of kind of interactions. It wasn't just one interaction. And the testimony today from the I.G. behind closed doors in Congress laid out what a tapestry of interactions.


And so, we're looking at more than one and more than just possibly Ukraine. We still don't know. But, you know, we're in this kind of bizarre point with the story here too. Where we know there's a complaint. We know people are taking it seriously. We know the president is involved. We don't know whose made the complaint. We're still unclear on the details. And you know, that does affect a lot of what we can say about it at this point.

LEMON: Yes. Juliette, listen, the president and Rudy Giuliani have both spoken before about their interest in Biden and Ukraine. This has been fairly out in the open. Is it a stretch that there could have been some conversations behind the scenes?

KAYYEM: Well, there's no behind the scenes when you're president of the United States. Giuliani is his personal attorney. He has no -- he doesn't represent me. He has no confirmed position. He's not even in the staff of the White House. So, he's sort of, this weird free agent.

But people know that he's speaks for the president. So, if Giuliani says something, everyone is going to know that -- you know, it's going to know that that is the same as if Don Jr. said something, that the president wants it.

So, there's the -- when you're the president you don't get alternative processes. That's the benefit, you know, that is basically it's a privilege to be president but you don't get to side deal. And that's essentially what appears to be happening across the world as we're seeing from Saudi Arabia to -- name -- to Mexico or wherever else Trump is putting his money.

So, it's just important that we realize there's no second Trump. There's no personal Trump when you're president of the United States. And I think that's key in this instance because when he's on a phone call saying, you know, I'm going to withhold a certain amount of money because I don't like Biden.

He is speaking not as someone who is, not as a private citizen who is running for office in 2020. He's speaking as a president of the United States. It is -- it is I'll just quote the I.G. - of grave concern. Now you can put a name behind it. It's illegal, it's impeachable. Let the lawyers decide that. But it's of grave concern that we and Congress should know about.

LEMON: Where does this go from here? Will we ever -- will we ever find out the truth, Asha?

RANGAPPA: I think that what is going to end up happening is that this is going to have to be litigated. My suspicion is that the White House is going to hang their hat on the constitutional article two argument they have essentially sort of unfettered discretion to have confidential conversations with foreign leaders and Congress is going to say no. We have oversight authority if that may break the law.

And when you have that kind of clash and they're unable to work it out on their own and the White House has continued to stonewall Congress on a number of other fronts, it ends up being up to the court to delineate where one power ends and another begins. And that may take some time.

LEMON: Listen, it was incredible risk for the whistleblower to come forward given the DNI and the DOJ how they handled it. What do you think happens next? I'll give you the final word, Matthew. ROSENBERG: You know, I think Asha is right. It's going to go on. I

think also you have an intelligence community full of people who feel that they have been disrespected by the president. And this includes the very senior officials as well.

You know, this is a situation where there are people who are incentivized to leak who do look inside and say, look, we got a process that's broke -- process that's broken. This is how you're supposed to do it. This is how the system is supposed to work. It's not working. The press are the safety valve, you know. And that's how this stuff gets out, that's how it eventually becomes public.

LEMON: Thank you, all. I appreciate it.

A fiery Rudy Giuliani tried to defend his boss, the president, on CNN TONIGHT. But did he make matters worse? Well, you're going to hear more of what he said. And that's next.



LEMON: The president's personal attorney -- personal attorney spending nearly half an hour obfuscating, spinning and avoiding questions from Chris tonight on the show before us.

While Rudy Giuliani initially denied asking Ukraine to investigate former Vice President Joe Biden, he then admitted doing just that just seconds later.

We have to talk about it. Frank Bruni is here, Ryan Lizza, and Rick Wilson. Rick is the author of "Everything Trump Touches Dies."

Good evening, one and all. Frank, Rudy Giuliani told Chris tonight that he didn't know what the president did. But, if he did do it, it was OK, and what Rudy did he did on his own. And he told the president about it afterwards. I'm sorry. What did we learn from this?

FRANK BRUNI, CNN CONTRIBUTOR: Well, I mean, we learned that Rudy Giuliani will say anything and mount any argument in his loyalty to the president which I don't quite understand. I don't quite understand a lot of this loyalty to the president.

But it's sort of absurd. Because we don't know what the president did, but regardless of what he did, it's OK. Now what we think he's talking about is the sort of -- is the sort of tit-for-tar aid in return for investigating Biden's son or something.

If that is the case, if that's the way these dots connect, absolutely that's wrong. I mean, we've just -- we've gone through a whole chapter of American history where you're been looking at foreign meddling in an election on whether that was solicited and whether there was collusion and all that sort of stuff.

And now we're looking at the possibility -- possibility --

LEMON: Right.

BRUNI: -- that the president invited it to happen again on his behalf even as the rest of this, you know, was kind of coming to a head. It boggles the mind. I don't know how to react to that, Don.

LEMON: Join the club. Rick, listen, I want to bring you in. Because Rudy Giuliani he contradicted himself multiple times. Shouted personal insults at Chris, at the network, and on and on. Here's more and then we'll talk about it.


CUOMO: You don't know what happened.


GIULIANI: I know what happened.

CUOMO: How do you know when I don't know?

GIULIANI: You know what? You are just repeating. You are just repeating spin. The prosecutor --

CUOMO: But you don't?

GIULIANI: -- the prosecutor -- and you want to cover some ridiculous charge that I urged the Ukrainian government to investigate corruption. Well, I did. And I'm proud of it.


CUOMO: It's not a ridiculous allegation. You just admitted it.


GIULIANI: All I can tell you is if what is reported is true, it doesn't make a damn. It doesn't make any difference. If the president of the United States said to the president of Ukraine, investigate the corruption in your country that has a bearing on our 2016 election. Isn't that what he's supposed to do?


LEMON: OK. Would he be that freaked out if there was nothing to the story?

RICK WILSON, REPUBLICAN STRATEGIST: You know, I've known Rudy a pretty long time. I've been around the block with Rudy since 1997. He's pretty amped up tonight. That was a pretty high intensity Rudy moment. And I will say the gem that came out of that essentially that we need to dredge up a little Watergate reference here, is he's basically saying if the president does it, it's not illegal.

LEMON: It's not illegal.

WILSON: Now as much as some people are fans of the unitary executive theory. There are things that are illegal, there are still things that are inappropriate. There are still unethical. There are still thigs that are immoral. And what Rudy described is in fact that behavior.

And you know, the fact that he admitted that he was pressuring the Ukrainians, you know, shows that this -- I hesitate to use this word because I'm not an attorney. It sounds like almost a conspiracy by Rudy's and Don's people to pressure the Ukrainians. You know, a high low game. Rudy goes over to ask the questions, Don makes the phone calls.


LEMON: Donald.

WILSON: I just -- I think we've delve into something tonight --

LEMON: Donald, Donald.

WILSON: -- that is pretty ugly.

LEMON: Donald. Donald.

WILSON: Wee little Donny.

LEMON: Don't say Don. All right.

Listen, Ryan, Chris is very fair to Rudy who was throwing out a lot of accusations. And then there was this. Here it is.


CUOMO: I'm sure they buy --


GIULIANI: They buy (Inaudible) that you are in the tank of the Democratic Party.

CUOMO: -- everything you're saying right now has nothing to do with distracting from what this president's problem might be

GIULIANI: I am not distracting.

CUOMO: You've been doing it for over a year and a half, OK?

GIULIANI: What I am pointing out -- I haven't been doing that.

CUOMO: Then hell, you have it. You've been distracting --

GIULIANI: What I'm doing is I'm pointing out how unfair you are and how you tried to frame the president.


CUOMO: -- from the truth for a year and a half and I hope you enjoy it because this president got the benefit of something you built up for decades. Your credibility.

GIULIANI: I'll put my credibility on the line --


CUOMO: And you put it on the line for him. Good choice.


LEMON: Wow. What's your reaction to that?

RYAN LIZZA, CNN SENIOR POLITICAL ANALYST: You know, I think in most of Rudy's appearances when he's defending the president on something is usually a debate as to whether he is just sort of mad, and I don't mean angry. I mean mad. And you know, flailing around and there's really no strategy behind what he's saying and, or is there a method to the madness and is he setting the stage for the arguments that they know they are going to need to make when facts come out.

So, if you remember in the Stormy Daniels case. Before all the facts of that case came out Rudy Giuliani was on air saying if the president did x, y, and z, what's the big deal? And that was before we knew that he had indeed done x, y, and z.

And so, the clip you played before this one, Don, that seems like the same play book. Saying, so what if he called the president of the Ukraine and said this. So that's --


LEMON: Does that mean, in your mind that he did it?

LIZZA: It's actually Rudy just touting off. You know, imagine the O.J. book, you know. If I did it. I -- so he's either giving us, you know, a clue to the coming defense and, you know, famous method of spin is to get those facts out ahead of time so it seems like it's old news. Or he's just, you know, completely just, you know, freelancing and this is not anything that's strategic.

But I don't know. It looks awfully like what he did on the Stormy -- in the Stormy Case. Getting ahead of what seems to be the coming story.

LEMON: OK. Frank, are you ready this? This is from Rudy Giuliani. Let's put it up. "A president telling a pres-elect of a well-known corrupt country he better investigate corruption that affects U.S. is doing his job. Maybe if Obama did that the Biden family wouldn't have bilked millions from Ukraine and billions from China, being covered up by a corrupt media."

By the way, there's no evidence of that. There's no credible -- but go -- I have no idea what that means. But go on.

BRUNI: But this is just insane. Because in the tweet he is seems to be confirming or at least suggesting that in fact what was going on was saying investigate Hunter Biden. LEMON: Yes.

BRUNI: Right before an election in which his most fierce some opponent might be Joe Biden.

Rudy Giuliani has sort of lost his mind here if he thinks that he's actually kind of pressing a persuasive case. I tell you when you pull back from this and when you watch that Chris interview with Rudy and the way he's behaving, it is perverse and it's just inexplicable that a president who least deserves this kind of loyalty, you know, and this kind of circling of the wagon and all that, gets it time and again.


And it's not just from Giuliani. He's the one making a fool of himself with Chris Cuomo there. But you know, Bill Barr protecting the president. He's seen -- and the Justice Department apparently has a role in all of this not telling, you know, the House Democrats what they want to know, the director of national intelligence.

Why are so many people willing to shelve their ethics and tick their necks so far out for this president of all people. It is one of the greatest perversions of this chapter of history.

LEMON: I think there's a tear in the universe. It's not just like Mercury in retrograde. I think there's like some space time continue on that it's like --

BRUNI: It's all a dream.

LEMON: It's all -- when are we going to wake up? Like is this like --


WILSON: It's the wrong time line.

LEMON: When is this episode of Dallas going to come to an end? When is it, you know, a dream who shot J.R.? Thank you all.

LIZZA: Thanks, Don.

LEMON: We'll be right back.

WILSON: Thanks, Don.



LEMON: President Trump's lawyer, Rudy Giuliani, giving a breathless contradictory and confusing defense of his boss tonight over reports that a whistleblower complaint about the president involves Ukraine.

And Attorney General William Barr now facing questions after sources tell CNN the Justice Department was involved in telling the acting DNI not to share that whistleblower's complaint.

Let's discuss now, Elie Honig, Harry Litman. Good evening, gentlemen. Good to see both of you. Harry, it has been a while. I'm going to start with you because I haven't seen you in a while.

So, President Trump's lawyer really all over the place tonight on these reports, the whistleblower complaint involves Ukraine. Did he make the situation even worse? What do you think?



LITMAN: So, yes. Look, there are these grand constitutional arguments that they're throwing around. But we have a really simple statutory scheme that has never been violated. It says the inspector general determines if you have this complaint. If you do, you transfer it over to Congress, to the Intelligence Committee, not to everybody in the country, to the Intelligence Community, which always looks at sensitive information and that's the basic oversight we have.

Now, has the president's lawyers made it worse? I do think we're coming into some sort of rough focus of what's happened and it may well be some kind -- what would be wrong with this Ukraine deal? Basically, it would be Trump trading something that belongs to the United States people, say the $250 billion in loans, for something that he wants for himself, not the country. Yeah, that would be wrong.

And I think it's getting, you know, clear enough and every day there's a drip, drip, drip. I actually think it may well not play out in the courts. There may well be an accommodation where they give the substance of this to Schiff, if not the letter of it, because I think Trump and company are getting clobbered every day in the news and it does get worse.

LEMON: Interesting. Listen, Elie, Giuliani flip-flopped tonight on saying whether he investigated Joe Biden. It is not the first time he's gone against his own words. Here he is. This is him talking to Fox News about the Stormy Daniels payment and then contradicting himself the very next morning. Watch this.


RUDY GIULIANI, ATTORNEY TO PRESIDENT DONALD TRUMP, FORMER NEW YORK CITY MAYOR: Having something to do with paying some Stormy Daniels woman 130,000? I mean, which is going to turn out to be perfectly legal. That money was not campaign money. Sorry, I'm giving you a fact now that you don't know. It's not campaign money. No campaign finance violation.

SEAN HANNITY, FOX NEWS HOST (voice-over): They funneled it through a law firm?

GIULIANI: Funnelled through a law firm and the president repaid it.

HANNITY (voice-over): Oh. I didn't know that. He did.

GIULIANI: He didn't know the details of this until we knew the details of it, which was a couple of weeks ago. Maybe not even a couple of weeks, 10 days ago.






LEMON: Is there a method to this madness?

HONIG: I don't know. Rudy tonight had like a Jack Nicholson, Colonel Jessup. You're damn right, I ordered the code red. The second time, Chris Cuomo --

LEMON: I did.

HONIG: Yes, I did. I mean, it's the Rudy three steps. Step one, deny it. Step two, admit it. Step three, yeah, it happened but it was OK, what's wrong with it?

I think we saw all three steps play out tonight. It is terrible lawyering. It's a shame to see from Rudy Giuliani who was -- look, he was the U.S. attorney for the Southern District of New York where I worked a couple of decades before. He was a legend. Now, he's a joke.

LEMON: You said it's -- so legally, you're talking about he's terrible lawyer. You said legally, having said that. But is it a good PR strategy, something good, something bad, and then something good?

HONIG: I don't know.

LEMON: No, yes, no.

HONIG: I don't -- I'm not going to say it's a good strategy.


HONIG: I know it worked kind of more or less with Stormy Daniels because Trump managed to fall between the cracks, aided quite a bit by the DOJ policy against indicting a sitting president. But the fact that it worked once I don't think makes it a good strategy. That is not -- young potential lawyers and law students at home, don't do this at home.

LEMON: Yeah.


LEMON: Don't do this. Don't try this on your own. Is that what you're saying?

HONIG: Yeah.

LEMON: Listen, the attorney general, Harry, William Barr, is under fire for advising the acting spy chief not to share this whistleblower complaint. You backed Barr when he was originally appointed attorney general but then took great issue with how he handled the Mueller report. Is this another example of Barr acting as the president's personal attorney?

LITMAN: Yeah, I got to say, you know, he's gone over to maybe not the other side but Trump's personal side. So for something like this, who are you going to call? Bill Barr. They will call on the OLC to produce some kind of tenuous opinion that will at least buy time.


LITMAN: Yes, you know, I do think it's of appease. Normally -- I wouldn't say normally -- universally, the DOJ wouldn't be involved here. Probably the White House had something to do with pushing the DNI to get the opinion and to arm them with something at least plausible that they can point to.

Sad to say, but the basic MO go to Bill Barr's Justice Department, get something you can say however outrageous about executive power to at least freeze the line backers. We have seen that before. This doesn't seem different given that the statutory scheme is so clear here and there's really no valid defense nor has there ever been any kind of attempt to resist this.

LEMON: I got to run. Thant's got to be the last word. Thank you, gentlemen. I appreciate it.


LEMON: Justin Trudeau. Blackface. Once, twice, three times? Maybe more.




LEMON: Canadian Prime Minister Justin Trudeau under fire as more images of him in blackface and brownface rock his reelection campaign. Trudeau apologized when the first photo surfaced showing his face and hands covered in dark makeup at an Arabian night's party in 2001.

Similar photo emerged from his time in high school, an appearance in blackface that he admitted to last night, wearing dark makeup and singing "Day Oh" as part of a talent show.

Now, a third instance has been uncovered, a video of him in blackface from the early 1990s. Trudeau says that he doesn't know how many times he's worn blackface in his life. Let's discuss now. Wajahat Ali is here, Tim Wise as well, the author of "White Like Me."

Gentlemen, good evening. Thank you both for joining. Last night, Trudeau, Wajahat, -- Trudeau said that there was only one other instance of him in blackface. But we have now seen a third. Listen to his follow-up apology today and then we'll talk.


JUSTIN TRUDEAU, PRIME MINISTER OF CANADA: This is something that I deeply, deeply regret. Darkening your face regardless of the context of the circumstances is always unacceptable because of the racist history of blackface.


LEMON: He seemed upfront about, you know, right away and contrite, but does that new video discredit him? What do you think of that?

WAJAHAT ALI, CNN CONTRIBUTOR: I don't think it discredits him but wearing blackface once is a one-time too many. For those of you who are wondering what to wear as a costume in October --

LEMON: Not that.

ALI: -- do not wear blackface. Thank you for coming to my TED Talk. That was free. Listen, this is a history of blackface, brownface, yellowface, has been used to dehumanize and ridicule and mock the other. That's what people need to understand. This is not just as being politically correct. This is not just as being race hustlers playing the race card and, you know, being reactionary. No.

There is a history here of using this type of makeup to dehumanize people of color in America and in Canada. I mean, I will give you one example, "The Birth of a Nation" in 1950, a movie that was a phenomenon, a racist movie that brought back the clan, used blackface. Look at the depiction of African Americans, as clowns, as unruly, as savages.

"Breakfast at Tiffany's," Mickey Rooney in yellowface with big teeth and slant eyes, right? An object of ridicule and mockery.

And so when Justin Trudeau, a grown man, wears blackface at the age of 30 as a teacher and also apparently did at the age of 21 -- Don, I am old enough to remember I was about 20 years old in 2001 at UC Berkeley, even then, I knew wearing blackface and brownface was a bad idea.

What I really want from him, I appreciate his contrition. I appreciate his apology. The question we should be asking is why did he not know this was wrong and how come nobody else told him? That, the answer to that question will bring this to a conversation this country doesn't want.

LEMON: Yeah. Tim, you know why. Tim, I'm sure. Go on. Take it away. TIM WISE, AUTHOR: Well, I don't believe that he didn't know it was wrong. I think the bigger problem with these incidents is that it's not just sometimes overt racism. Sometimes it is. We see these incidents on college campuses, for example, where folks have ghetto parties on MLK Day and they put on blackface. That's pretty blatant. There's no subtlety there.

I don't think that's what Trudeau is guilty of. I don't think that's what a lot of cases are. But what they are about is white folks, whether it is in Canada, the U.S. or in Europe where these things have also happened, who have so little regard for the life experiences and the history facing black and brown folks, that they just sort of -- they sort of know it's wrong, they sort of know it's more than just transgressive, they know it's more than just edgy, they know it's offensive.

At the end of the day, they go, yeah, but you know, it's Halloween or it's a party. Here's the message that I think folks need to understand. It's one that I understood by the time I was five but maybe my parents are better than some parents. The lesson is this: Blackness is not a costume. Indigenous Americans. They're not characters to be played either.

You don't just put on someone's hair or makeup or skin color as a costume. These are people with lived experiences and whether you are doing it to intentionally denigrate or you are doing it because you have the privilege of being stone cold ignorant to the reality of other people's lives and still be called educated, whichever one of those it is, is a problem. We got to do better. I mean, the contrition is necessary.


WISE: But we as a culture better ask why it is that white folks in North America and around the world are allowed to be this stupid and still be considered leaders, still be considered intelligent, still be considered educated enough to graduate high school, let alone college. It's unbelievable to me.

LEMON: Listen, Wajahat, you both mentioned contrition. You can appreciate the contrition which I said last night and also condemned the act which I said last night. Conservative media taking out of context just saying that I praised him. What I was saying is it's actually refreshing to hear someone apologize when they did something wrong because that never happens lately here in the United States.

But also condemn what Justin Trudeau did at same time. And he did acknowledge, which many people don't, his white privilege, right? He didn't make excuses for it. But, does that really change anything?

ALI: No, he admitted his privilege, but it reflects also that ignorance is itself a privilege, right? He didn't know he said. So you have to take a step further. This is an election year. We see the rise of white nationalism in North America and Europe. If you really want to tackle this, Don, we have to have a conversation in this country about something we never talk about. Ready? White supremacy. Until you get to the systemic racism that causes something like blackface to occur again and again and again and for worldly intelligent people like Justin Trudeau, a liberal, who wears blackface as a grown man and doesn't understand why this is harmful, this will keep happening. That's the conversation this country needs. We want to get to reconciliation without truth. We got to tackle truth. It is going to be uncomfortable.

LEMON: Wajahat, listen, I have to go here, but can you just -- please, I want you to talk about -- your daughter has liver cancer. She is in need of a donor. How -- if you don't mind talking about it, how is that going, the search, and how is she going?

ALI: Yeah. Thank you so much for asking. My Nusayaba, my warrior princess just turned three. She was diagnosed with stage four liver cancer in April, hepatoblastoma. It only affects one percent of kids. It is so rare. She finished her ninth chemo. She's a brave little warrior. She is smiling today. She had her (INAUDIBLE). She had recovered since the last chemo. She's doing well.

We're still searching for a perfect match. Over 500 people have applied to be liver donors. Thank you to the CNN family. I just want to tell everyone who is watching right now, I never asked anyone at CNN, but all the hosts and the producers went out of their way, even your producers today went out of their way to say how can we help, how is she doing, we are rooting for her.

And so let's just hope. If you send thoughts and prayers, send me your thoughts and prayers. I do believe in God. We will take all the prayers. She is looking for one match, just one match right now. Let us just hope she gets a liver donor.

LEMON: We communicate, we text, we e-mail. You didn't even tell me.

ALI: I did not.

LEMON: Yeah, I know. You owe me a text too because --


ALI: I have been busy, man.

LEMON: I know you have been busy.

ALI: Blackface, cancer, you know, Rudy Giuliani. This is America.

LEMON: I got to run. We wish you the best. Anything we can do. Thank you. Thank you as well, Tim. We'll be right back.

WISE: You bet. You bet.



(COMMERCIAL BREAK) LEMON: A major democratic donor is facing a host of charges and many people wonder why it didn't come sooner. Stephanie Elam has the story.


UNIDENTIFIED MALE: We had so many naysayers tell us that we would never see this day. Buck will never be arrested. And this is just a small step towards victory for my brother, for Timothy Dean.

STEPHANIE ELAM, CNN CORRESPONDENT (voice-over): Wearing a blue suicide prevention smock, Ed Buck, a well-known democratic donor, stood in court to face charges brought by the Los Angeles County District Attorney's Office, including felony battery, administering methamphetamine, and maintaining a drug house.

Narcotics paraphernalia found inside his apartment, including meth and 24 hypodermic needles, officials say. In federal custody, charged with providing methamphetamine that led to a man's death. The federal law is offering tougher sentences.

The Los Angeles D.A. says a 37-year-old man was given a large dose of methamphetamine by Buck in Buck's apartment in early September. Fearing he was overdosing, the man, who was living with Buck at the time, left to get medical attention. But on Septemeber 11th, he received two more large doses of meth, also allegedly administered by Buck. The man eventually fled to a nearby gas station and called 911. The man did overdose but survived.

JACKIE LACEY, LOS ANGELES COUNTY DISTRICT ATTORNEY: The surviving victim's statements gave us the break we needed. It gave legally sufficient evidence to establish the charged crimes and prove the case beyond a reasonable doubt in state court.

SEYMOUR AMSTER, ATTORNEY FOR ED BUCK: We will fight this case vigorously, but I'm not so sure legitimately there was ever enough evidence to ever cause this case to be filed until recently.

CROWD: Arrest Ed Buck!

ELAM (voice-over): The outrage surrounding Ed Buck has been boiling for years, after two men died in his apartment in similar circumstances in less than 18 months. On July 27th, 2017, Gemmel Moore was found dead of an accidental meth overdose. But the D.A.'s office, claiming insufficient evidence, declined to press charges.

Timothy Dean also died in Buck's apartment on January 7th of this year, also of an accidental meth overdose. Why it is Moore's death that is the crux of the federal charges against Buck, today, the U.S. attorney revealed there are many more men that say they were victimized by him.

NICK HANNA, U.S. ATTORNEY: Investigators have located 10 additional victims, nine of whom said Mr. Buck administered drugs to them or strongly encouraged them to ingest narcotics as part of agreements to be compensated for sexual services.


ELAM (voice-over): Handcuffed and slumped over in the back of a police cruiser, Buck was taken away outside of his West Hollywood apartment Tuesday. It's a strikingly different posture for the LGBTQ activist and prominent donor who has contributed more than $120,000 to democratic heavyweights since the early 90s. That is according to the Center for Responsive Politics.

JASMYNE CANNICK, FAMILY SPOKESPERSON: For the past two years and 53 days, we had a lot of people telling us that nothing was ever going to happen to Ed Buck because he was this white, gay man who had a lot of money and a lot of influence in Los Angeles.

ELAM (voice-over): It's a sentiment others have long held, that Buck's power and privilege had kept him safe. But the D.A. pushes back on that.

LACEY: We have done and we will continue to do everything legally possible to put this depraved sexual predator away.


ELAM: If convicted, Buck faces up to life in prison. Also outstanding is the wrongful death lawsuit filed by Gemmel Moore's mother against Buck in February. Don?

LEMON: Stephanie, thank you so much. And thank you for watching. Our conch continues.