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Laura Coates Live

Laura and Team Analyzes Day 9 of Trial; Suspect Charged with Murder in Israel Embassy Staff Shooting; Will Sean "Diddy" Combs Take the Stand?; Laura Coates Interviews Director Yoruba Richen. Aired 11p- 12a ET

Aired May 22, 2025 - 23:00   ET

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

[23:00:00]

PETE SEAT, FORMER WHITE HOUSE SPOKESMAN FOR PRESIDENT GEORGE W. BUSH: A few weeks ago, I -- I broke one of the sacred rules of the nightcap. I went 42 seconds instead of 30 seconds.

ABBY PHILLIP, CNN ANCHOR AND SENIOR POLITICAL CORRESPONDENT: All right --

SEAT: Very short today. Two words. Emma Watson. That's --

(LAUGHTER)

PHILLIP: Yeah. So, none of the you all wants somebody to pack and unpack the dishwasher.

All right, before we go, I want to mention that Montel has a new book out and it is called "The Sailing of the Intrepid." It is out right now. You could go get it in stores.

MONTEL WILLIAMS, TALK SHOW HOST, ACTIVIST, AUTHOR: Anywhere you can buy a book right now. I'm actually doing a signing on the "Intrepid" this coming Sunday.

PHILLIP: All right, if you're in New York City. Everyone, thank you very much. Thanks for watching "NewsNight." You can catch me on your favorite social media. In the meantime, "Laura Coates Live" starts right now.

LAURA COATES, CNN HOST AND SENIOR LEGAL ANALYST: Good evening. Welcome to the special edition of "Laura Coates Live: Diddy on Trial." And day nine was a wild one in the criminal case against Sean Combs. The prosecution called rapper Kid Cudi to the stand, and he said Diddy was like some sort of Marvel supervillain when they finally came face to face. In just a moment, my legal experts and court insiders will break down what he and four other witnesses told the jury today alone.

And if any of it is advancing the prosecution's racketeering case, the big bombshells? Kid Cudi said that he believes Diddy broke into his Hollywood home and was behind the torching of his Porsche after finding out that Cudi was dating Cassie Ventura.

A makeup artist who worked for Diddy and Cassie testified that she saw signs of abuse and let Cassie stay in her own home after one violent encounter.

And the manager of a hotel in Beverly Hills revealed records showing Diddy routinely trashed his hotel rooms.

Now about that Kid Cudi testimony, it was fiery figuratively and, of course, literally. He told the court that he started dating Cassie around 2011. And in December of that year, Cassie told him, Diddy had found out about us.

The same day, he said that he got a call from a Diddy employee who told him that Diddy was at his house. So, Cudi, he went home, and he called Diddy on the way. He said it went something like this: I said MF-er, you in my house? And he was like, what's up? I was like, MF, are you in my house? And he said, I just want to talk to you. I was like, I'm on my way over right now. He was like, I'm here.

Now when Cudi got home, no one actually was there, but he says security cameras had been moved angled away from where they were originally pointed before he left his home. Gifts from Chanel that he had in his for his family on a kitchen counter, they've been opened. And his dog could normally roam free around the house, was suddenly locked in the bathroom.

And you fast forward to January 2012, Cudi testified that this happened: His dog watcher called to tell him that his Porsche was on fire. The jury, well, they saw these images, and Cudi said it looked like the top had been cut open and a Molotov cocktail was dropped inside. The prosecutor asked, what was your reaction to your car being set on fire? Cudi said, what the F?

Now he testified he met with Diddy at a member's only club the next day. He walked into the room, Diddy was alone, and he said he saw this: It was one wall was all windows and Sean Combs was standing there staring out the window with his hands behind his back like a Marvel supervillain.

They ended up talking about Cudi's relationship with Cassie and how neither of them seemed to know that the other was actually dating her at the same time. Diddy denied any involvement in blowing up his car or setting it on flame.

Now the witness called after Kid Cudi is someone I've actually spoken with on this very show, makeup artist Mylah Morales, who worked for Diddy and Cassie. Now she testified about an incident at a hotel in 2010 where she saw Cassie right after Diddy -- Diddy had beaten her up. Well, what she told the jury matches what she told me last year during her first interview.

(BEGIN VIDEO CLIP)

MYLAH MORALES, FORMER MAKEUP ARTIST FOR DIDDY AND CASSIE: Once she came out of the room, she was badly, you know, beaten.

COATES: Oh, my God. What it -- what did her physical appearance look like?

MORALES: I mean, it was knots on -- her knots on her head, black eye, busted lip, but a lot of knots all over her head.

(END VIDEO CLIP)

COATES: Morales said that she let Cassie stay at her home for a few days after that. Then came a hotel manager in Beverly Hills. I told you it was a packed day in the courtroom. The jury saw notes from Diddy's record at the hotel, and one said this: Always spills candle wax on everything and uses excessive amounts of oil, place the room out of order upon departure for deep cleaning.

[23:05:03]

Leading us off tonight is CNN's Kara Scannell, who has been in court every day of this trial. Kara, despite Kid Cudi indicating that Diddy was behind the Molotov cocktail that he says set fire to his Porsche, he also noted he had found peace with an apology that he received from Diddy a few years later. What happened?

KARA SCANNELL, CNN CORRESPONDENT: Yes, so, after the Molotov cocktail incident, Kid Cudi said that he reached out to Combs and because Combs had been trying to get in contact with him and he wanted to settle things. So, he said that they agreed to meet at the Soho house. This was in January of 2012.

And he said he walked into the room and Combs was standing in front of glass windows with his hands behind his back, which Kid Cudi said made him look like a Marvel superhero villain, and said that he then had this meeting with him where they discussed Ventura, them dating, and he said that they shook hands at the end. And he said to Combs in that moment, what about my car? And Combs said, I don't know what you're talking about. And so, Kid Cudi testified that he thought Combs was lying.

Then it was three years later, in 2015, he runs into Combs at the Soho House. He said Combs is there with his daughter. He pulls him aside and he says, you know, I apologize for everything that went on. And so, Kid Cudi said that he made peace with that because he didn't think he would even get any kind of apology and he just moved on.

So, after his testimony today, he went to Instagram and he posted a story thanking people for supporting him.

(BEGIN VIDEO CLIP)

SCOTT "KID CUDI" MESCUDI, RAPPER: I just want to say thank you so much, man. People been hitting me up the past week, just checking in, and even today, and I just -- it really means a lot to me, man. This is a stressful situation. I'm glad it's behind me.

(END VIDEO CLIP)

SCANNELL: So there, that's what he -- his last message was to his fans. He wasn't on the stand that long but certainly something that the prosecution that would be important for their racketeering conspiracy part of this case. Laura? COATES: You know, hearing him testify in person was really something. I think everyone was waiting to figure out what he would contribute to the overall prosecution's case. He is a prosecution witness. He was crossed by the defense.

But one of the things that they were able to get during that cross- examination from Diddy's defense counsel, he described in court feeling played by Cassie, that she, one, was actually dating him while dating Cudi, also that she returned to him and was back together with him during that Soho meeting, and that she had also played Diddy. Tell me about that.

SCANNELL: Yeah. So, this was during cross-examination. The lawyer for Combs, Brian Steele, is asking Kid Cudi about his relationship with Ventura and saying, you were in communication with her basically every day in some form or another for most of 2011. And Kid Cudi says, yes, they were. He -- you know, they -- they only started kind of getting romantically dating later, but they had this relationship. And his understanding from Ventura was that she was no longer involved with Combs.

So, then, Brian Steele says to him, you know, the person who played you is the same person who played Sean, it's Ms. Ventura, true? And Kid Cudi says, true.

And, you know, this all goes to part of Combs's defense, which is that Cassie Ventura was not coerced or controlled by Combs, that she was making her own decisions. And so, this is something that his team is going to seize on to -- to show that she was involved with someone else. She could have left this relationship, but she went back to Combs. Of course, the prosecution has a different theory, but this testimony was something that they did try to jump on today.

COATES: Did Kid Cudi and Diddy interact at all?

SCANNELL: You know, it's interesting. Kid Cudi walked in to the courtroom. It was kind of a moment because everyone was waiting for him. His name has been discussed for days. You know, he's wearing a leather jacket. He's got a dangling earring. He walks down the center aisle. There are rows on both sides. And Combs is facing forward. He doesn't see him. And then when Cudi crosses kind of this threshold, you see Combs look over to him, but at that point, there was no eye contact because Kid Cudi had already passed.

When Kid Cudi was on the witness stand, most of his attention was really focused on the lawyers asking him the questions. I didn't see him really make any effort to make eye contact with Combs. And then when he was leaving the witness stand, Combs seemed involved in talking to his attorneys. So, it didn't seem like there was any interaction between these two former boyfriends of Ventura.

COATES: Kara Scannell, thank you so much.

With me now, my all-star legal panel. I have former AUSA Gene Rossi, trial attorney and legal analyst Monique Pressley, represented Bill Cosby in the past, and former federal prosecutor Alyse Adamson also here.

Let's unpack this all. Alyse, let me begin with you. Listen. Having Kid Cuddy testify, everyone was leaning in. They were very much engaged. It talked about his Porsche being set on fire, this love triangle that Diddy and Cudi were unaware of, apparently.

[23:10:00]

But does it move the needle on the RICO racketeering case?

ALYSE ADAMSON, FORMER FEDERAL PROSECUTOR: Laura, I think it absolutely does because if you read in the indictment, the arson is one of the predicate offenses for the racketeering activities that the government must prove. And that's just -- that's a crime that has to have been committed at the direction of this corrupt enterprise. And that's what they're getting at this arson. And so, they were laying a very strong foundation.

The defense on cross, well, they tried to make it seem like Kid Cudi had no idea who had blown up his car. And that's true. He wasn't there. But they completely ignored the fact that Cassie had just testified that Sean Combs has, in fact, threatened to blow up Kid Cudi's car.

And so, there is that link there that prosecutors drew out very early, and I think that was a huge score for the prosecution.

COATES: Do you agree?

GENE ROSSI, FORMER FEDERAL PROSECUTOR: Absolutely. Well, of course, Alyse said it, so I agree.

(LAUGHTER)

You said --

COATES: I love a prosecutor, defense attorney having the same viewpoint.

ROSSI: You said be conversational. The reason I like this witness, and it follows up to what Alyse just said, I look at an indictment. And when I'm a prosecutor, I'm always thinking about what are the elements of this -- of this charging document.

And for RICO, you need an enterprise. And it's easy to prove the enterprise. It's a who is -- his business, his enter -- his empire. You need to connect this arson to the enterprise because he's using at least one or two associates to help him break into Cudi's home, and inferentially, by circumstantial evidence, he torched the Porche -- the Porsche with the Molotov cocktail. So, you're -- you're connecting the arson to his use of the enterprise.

COATES: Hmm.

ROSSI: It's sort of like "The Sopranos." You can't just separate them. And I think they -- they connected one key dot by the arson by connecting it to the enterprise because he's using employees to help him out, and he has the motive to do it.

COATES: Well, Monique, do you see it the same way? Because on the one hand, I think he's pulling about the -- I mean, it's called Bad Boy Enterprise. Right? And, of course, his whole umbrella of entities is included, whether it's liquor or clothing or lifestyle, etcetera.

It sounds like he's suggesting that because that enterprise exists and then an arson occurred, the enterprise works to actually commit just those crimes.

MONIQUE PRESSLEY, TRIAL ATTORNEY: I mean -- and -- and it's very much like "The Sopranos" right now because it's fiction. Like, there's no actual evidence of it that has been entered in at trial. I was wondering as I was reading it, where was the other crime's exception? Like, how is it working in here when you've got a witness on the stand who says that some other witness said that their car is going to get blown up? Do I know who blew up my car? No. Was it there when my car was blown up? No. Was I aware that the DNA for the person that was found in the car was a female, not a male? No.

I mean, maybe it's -- maybe it's the defense attorney in me, but I do believe that if you're charged with crimes, then the high standard for a criminal trial is beyond a reasonable doubt.

And in the land of, you know, wishes, hopes, and dreams, we could say he's using his enterprise like having a business, which isn't against the law, and we've got these employees. Who are they, by the way? Who are helping him to do what? Exactly, none of that is in evidence at this point.

COATES: There was a moment, too, when they did suggest, you know, objections. No one has actually been charged for the crime of the car. And I wondered how that was going to hit with the jury because, again, they're trying to connect dots of what, ultimately, they'll be asked to do. RICO, sex trafficking and, of course, prostitution. Do you think that there is a risk that the prosecution has not connected the dots at this stage yet?

ADAMSON: I think they're connecting them. As my teenage daughter might say, we got to let them cook. Right? This is the Southern District Of New York. They have a very high conviction rate. I do agree with you, Monique, that they haven't completely connected them all, but I think they're laying that foundation.

And remember, this is racketeering conspiracy. All they need to prove is that Combs entered into an agreement for this predicate act or this arson to have been committed. And they haven't. This is like week two. They have six more weeks. They're probably going to call more employees to finish connecting those dots, because I agree with you, if they don't, they're not going to get it. But I find it --

COATES: That's six more weeks of thinking. I mean, I had to tell you, six more weeks of trying to do -- what -- what they're doing would be surprising. I mean, that might include, obviously, the defense case as well. But then you have what the prosecution -- the prosecution, as we know, has the burden approved. Their order of witness isn't who they're calling. They've called a L.A. hotel manager to talk about the rooms being trashed. Obviously, "freak-offs" aftermath. They've got the makeup artist who is talking about this violence and what she has seen. You had a number of people talking about domestic violence.

The defense day one opening statement, he's a domestic abuser, we own that, he's not the other things.

[23:14:58]

What does the makeup artist or the L.A. hotel employee, how does that move the needle, you think?

ROSSI: Well, can I just add a rebuttal to what the great professor just said?

COATES: No.

ROSSI: No?

(LAUGHTER)

ROSSI: Alyse brought up a point that Cassie Ventura mentioned that Combs had threatened to commit arson on her car. Okay? So, Cudi may not have directly seen Combs do the dirty deed, but it corroborates what Cassie said. Point number one. Now, let's go to what you asked about --

COATES: But wait. Before you do it, now we can take a little dip for a second. Let's -- let's -- let's say that --

ROSSI: Yeah.

COATES: -- Combs, in fact, did commit the arson, and he had denied --

ROSSI: Okay.

COATES: Let's say he did so.

ROSSI: Yep.

COATES: Does it help the prosecution that now it looks as though there is a tangible result of his insane jealousy? But is it enough to show that a criminal enterprise has helped to facilitate sex trafficking and the like?

ROSSI: Yes. If -- if you have a business, it could be a legitimate business, and his was for most purposes.

COATES: Uh-hmm.

ROSSI: If you are using that business, employees, independent contractors, friends, associates to do a pattern of criminal acts to threaten people so that you can engage in sex trafficking or just the Mann Act, if you're using those employees --

COATES: The Mann Act is traveling across state --

ROSSI: Yeah.

COATES: -- sexual purposes.

ROSSI: And you don't need force, a fraud or coercion. If you're using your business, whether it's a lumber business, a farm, or Combs' enterprise, and you're using it commit a pattern of related acts to commit sex trafficking, Mann Act, then that's RICO. You have satisfied RICO.

COATES: Hmm.

ROSSI: I want to just say this. I've done -- I've done a fair number of trials. And -- too many. But the first day, the first week, the second week of a trial, if it's going to go eight to 12 weeks, it -- it's the slow cooker thing, you know, the crock pot. You have to have a series of witnesses that connect the dots, and I think they're doing that.

COATES: Well, the only way to have a good crock pot meal is to season it well.

(LAUGHTER)

And I'm not sure if the salt and pepper is there right now.

ROSSI: I like salt and pepper.

COATES: We're just going to make sure. We got to have a lot more on there. But really quick, Monique, one of the things that they were trying to suggest was that both men were salty. You know --

ROSSI: Yeah.

COATES: Both men were salty about the fact that they were being played by Cassie Ventura. That runs directly counter to the image the prosecution wants the jury to have of somebody who is helpless, who feels trapped, and could not possibly have ever been able to leave Diddy Combs without severe repercussions, violence or revenge porn.

He describes that she -- he played them, that for a year, they were uninterrupted in the ability to communicate and be together. What might that do to a jury who is trying to balance who they heard from the stand and who was described by Kid Cudi?

PRESSLEY: They're going to be looking at it and trying to figure out whether the person who they were looking at that day is the same as the person who's being described a decade earlier or not and what it means.

What's off the table is whether she was abused or not. As we talked about earlier this week, to me, the domestic violence has been proven, and they've seen it with their own eyes. Now what they're going to assume about that, whether they accept this Hughes testimony or not, which to be is, like, a pupil issue, number one, because --

COATES: That's the psychologist who talked about the general patterns of what someone might do if they are abused.

PRESSLEY: Utterly completely useless. She has never met with and assessed and evaluated Ms. Ventura. So, why is she even on the stand? But that's just me. So, we can't use her.

But what they're going to look at and say is, okay, well, at some point, she had some agency. And at some point, she was making some decisions. What decisions was she making? And was this really a horrible love story, a horrible violent relationship as opposed to a criminal enterprise?

And that's why I said, you know, these are two good prosecutors. I'm not prepared to say that that's what I'm seeing.

COATES: You know what? Later in the show, we're going to be talking to Johnny Depp's attorney --

ROSSI: Ben Chew.

COATES: -- who -- Ben Chew, who actually also has a little familiarity with the person that you say may have had a useless testimony. I'm talking about that psychologist. I'll be curious to pick his brain. Everyone, thank you so much.

ROSSI: Thank you.

COATES: We'll have much more on the trial later this hour. But first, the very latest on that shocking shooting in Washington, D.C. that broke on air last night. Two Israeli embassy staffers gunned down by a man who then shouted, free Palestine. That man is now charged with murder, and police says that he's confessing to it all. What the investigation is revealing, next.

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(COMMERCIAL BREAK)

COATES: Breaking last night during our show, in fact, an unconscionable tragedy outside an event at the Capitol Jewish Museum right here in Washington, D.C., really a few blocks away.

Two young Israeli embassy staffers who were about to get engaged were gunned down by Elias Rodriguez from Chicago, leaving friends, leaving coworkers, leaving families reeling.

(BEGIN VIDEO CLIP)

YECHIEL LEITER, ISRAELI AMBASSADOR TO THE U.S.: Yaron's office was just a few doors down from mine. Sarah come in every morning with a smile, with her red hair blazing, and the sun rising.

[23:25:01]

So, we miss them very much, and it is real trauma that we're in.

NOA GINOSAR, FRIEND AND WORK SUPERVISOR OF SHOOTING VICTIM YARON LISCHINSKY: They had the same positive energy, the same calm and quiet, but desire to -- to do good things and to do important things and to live a -- a life of purpose.

(END VIDEO CLIP)

COATES: A few hours ago, the Justice Department charged the shooter with federal murder charges for cutting short the lives of Yaron Lischinsky and Sarah Milgram. The DOJ says it is investigating this murder as both an act of terrorism and a hate crime. Police say the suspect told them he committed the heinous act for Gaza. Now, as we've learned today, the event the couple was attending was focused on humanitarian aid efforts to Gaza.

With me now, former chief of Homeland Security and Intelligence for the government in Washington, D.C., Donell Harvin, and Rabbi Hyim Shafi -- Shafner, excuse me, of Kesher Israel, the Georgetown synagogue.

Gentlemen, thank you both for being here. Rabbi, let me begin with you because you live in this area, and it's a hot skip and a jump from where we are right now, which means it's close to all these major agencies and entities. What have you heard from the community of people around here?

RABBI HYIM SHAFNER, KESHER ISRAEL, THE GEORGETOWN SYNAGOGUE: Yeah, I was at a -- I was at a vigil tonight at the White House, you know, in front of it at 8 p.m. And I -- and I said to people, I said, you know, how are your friends feeling? How are you feeling? I talked to my congregants.

People are worried. People are afraid. Somebody from our congregation called my wife this morning and said, should I send my child to preschool today or not? You know, it's at the JCC, and I'm worried. So, you know, what does it -- what does it mean to be in a country built on religious freedom and be afraid?

COATES: That fear is so impactful all across the nation, not just when it happens in some place like Washington, D.C., but it has a ripple effect. And I know the investigators are looking, Donell, at the suspect's digital foot footprint as well, a possible manifesto that has been circulating on the web.

Could you just describe a little bit about how his internet activity and digital footprint might aid the government's understanding of what he is alleged to have done?

DONELL HARVIN, FORMER CHIEF OF HOMELAND SECURITY AND INTELLIGENCE, DISTRICT OF COLUMBIA: Well, the first thing I'll say is that lone actors are always the most difficult to detect and interdict. That said --

COATES: Why is that? HARVIN: That said -- because there's no network to interrupt. There are no communications between other individuals. Often these lone actors will reach out to somebody for weapons or some type of tactics to assist them. When they're operating by themselves, they're really operating under the radar unless they have what we call leakage, which is where they may be online and they'll post something against the community or they'll say they want to do something which, apparently, this individual did.

If it's that's done with enough time and people have the wherewithal online to report that to law enforcement, then that's an opportunity to interdict them. But often, we see these individuals post these things and then go immediately out and -- and mobilize to violence.

COATES: He traveled to right here for a work conference. He had a legally purchased firearm on his hand that he actually declared in his checked bag. No criminal records. Does that worry you about copycats or worry you about the ability to prevent something like this?

HARVIN: We -- unfortunately, we've known this for the last few years. The last two DHS homeland threat assessments that have been issued by Homeland Security have stated that crimes against the Jewish community are on the rise. And so long as the conflict in Gaza continues, the Jewish community needs to protect themselves against things like this.

COATES: Rabbi, antisemitism is increasingly -- it seems a tale as old as time. But the numbers have escalated certainly since what Donnell has described. But how has the rise of antisemitism, particularly in the last several years, contributed to the feeling of not feeling safe and being able to be among the world?

SHAFNER: Yeah, you know, if -- if you had told me 20 years ago that you wouldn't walk into a house of worship, a synagogue without police, I wouldn't have believed it. But today, it's true. You know, I have congregants who walk around the city and worry, you know, should I -- should I wear my kippah? Should I wear my Jewish star? Am I -- I -- I feel that way sometimes. You know, it feels dangerous.

COATES: What do you tell them?

SHAFNER: You know, on the one hand, you want to be proud. You want to be able to be an American who's proud of your individual religious life. On the other hand, I understand it. I understand the fear. It's real.

COATES: Do you have a sense that there's anything that can be done through legal action? Hate crime prosecution, investigations that would make people feel safer? I see from your facial expression, it doesn't seem to be.

SHAFNER: Well, as you pointed out, antisemitism has always been there. It rises and it falls. If it's rising, we have to ask ourselves why. You know, it's -- it's a bit of a trope to say Jews were a canary in the coal mine, but if this is happening, we have to ask ourselves, where -- where is it coming from?

[23:30:02]

What does it mean to live in a culture where people are divided, where people hate each other, where that's feeling like it is part of the matrix here? And so, a lone actor, right, they might just tune into that. And -- and -- and we have to somehow create, you know, a different kind of culture, I think.

COATES: Where does that start?

SHAFNER: Well, it starts from all of us, you know? It starts from all of us trying to understand people who are different. We -- we all know that people of -- you know, different politics than our own. Right? We -- instead of thinking, oh, they have a different way of seeing the world, we think, oh, I hate them, I got to get rid of them.

COATES: Hmm.

SHAFNER: We talk about this all the time. But it -- it -- it enters the hearts of human beings. It's -- it's -- it's -- we have to be responsible for American culture. Jews are just a tiny percentage of the world and of America, and -- and we all have to come together to realize that hatred is not just -- we can't just, you know, blame what's happening in Israel today or this or that.

We have to realize that this is -- it's -- it's -- this is the sensitive moment. We have to take this as instruction to build a different kind of society.

COATES: Quickly.

HARVIN: I just want to buttress what the rabbi said. Jews make up about 2% of the U.S. population. But last year, they were targeted almost 70% in the hate-related -- hate crimes related to the FBI standards.

Jewish and antisemitism, hate-related crimes have risen almost a thousand percent in the last decade. And so, really, less talk, more action needs to happen in order to protect these communities.

COATES: When will it end? Donell Harvin, Rabbi Shafner, thank you both.

Still ahead tonight, it's one of the big questions that is looming over the criminal trial against Sean "Diddy" Combs. Will he take the stand? My next guest successfully represented Johnny Depp in that blockbuster defamation trial where we saw many similar themes of alleged domestic abuse emerge. So, what does he think Diddy and his legal team should do? He's here in studio to share with us, next.

(COMMERCIAL BREAK)

[23:35:00]

(COMMERCIAL BREAK)

COATES: Well, let's get some perspective now on what it was actually like inside that courtroom as rapper Kid Cudi took the stand today. Christine Cornell, who has been our eyes and our ears inside the courtroom, keeping a very close eye on all the testimony to bring you these sketches you've been seeing all night and throughout the trial. Christine, how is Diddy behaving during Kid Cudi's testimony?

CHRISTINE CORNELL, COURTROOM SKETCH ARTIST: You know, I -- I was just watching and listening.

COATES: Uh-hmm.

CORNELL: I actually did see Kid Cudi glance at him once. Now I can tell you that, you know, it's the luck of the draw whether or not you catch such a thing. But I do notice that a lot of witnesses don't engage with Puff. And he looked at him once.

COATES: Describe that glance. What kind of glance was it?

CORNELL: It was a connecting glance. You know? I mean, these two -- what did he -- he refer to Combs as, his homie? That's why they had to get together and straighten this out. You know, mano a mano. I love it that he said he was going to go fight him. I'm going, oh, yeah.

COATES: That was the moment he was describing. Just so -- as I said, that was the moment he was describing, realizing that Diddy was at his home once he had discovered that he and Cassie Ventura were dating, and he was waiting for him.

CORNELL: Right.

COATES: And then while going back to his home, Cudi said he's going to try to confront him. He was not there, ended up calling the police instead.

Christine, I want to know about George Kaplan. That was the former assistant that testified today. And he seemed to be --

CORNELL: Yeah.

COATES: -- really professionally in awe of Diddy and his experience in spite of --

CORNELL: Right.

COATES: -- his decision to leave because he says he witnessed violence against women. At one point, he called him an icon and called him a "god among men," said he still wishes Diddy a happy birthday every year. What was Diddy's reaction to this kind of testimony that was really, really effusive towards him?

CORNELL: He was soaking it up. He was smiling. He was nodding vigorously. He was really digging the flattery. It was quite impressive and over the top, the flattery, frankly, you know. But the one little funny little twist that I didn't see Diddy react to was when Kaplan said, I invited him to my wedding, but I never heard from him.

COATES: Didn't react to that.

CORNELL: He didn't react to that, but he -- he reacted to oh, yes, you do wish me happy birthday.

COATES: Christine Cornell, thank you so much.

CORNELL: Okay, ma'am.

COATES: So, what's the key to defending a celebrity client in a high- profile case like this one? Let's ask my next guest who successfully represented Johnny Depp in his defamation suit against his former wife, Amber Heard. Benjamin Chew joins me now. So many questions about this whole trial and what people are thinking.

[23:40:00]

But I want to know what your assessment is. Which side, do you think, has the upper hand right now?

BENJAMIN CHEW, CO-LEAD COUNSEL FOR JOHNNY DEPP IN HIS DEFAMATION TRIAL: I think the prosecution is doing well. I think they were wise to start out with the tape that the rest of us have all seen because I think that gets the jury less thinking about Diddy for all of his success and his celebrity and start seeing him in an unfavorable light. So, they're prepared for what the prosecution is going to do next, which is to build the building, the edifice of their case, which I think they're doing well.

COATES: The racketeering and RICO charge, having to define that enterprise and connect it to crimes, is often a challenge for any prosecution team. Will it be more so here with such an expansive scope of businesses?

CHEW: I think they're -- again, I think they're -- they're building the case very carefully, and I think they're establishing the elements. As -- as you pointed out, this is a very long trial, so a lot of us are eager to kind of get to the end, but I think they're methodically going through and establishing the elements.

For example, I think they've already established all the requisite elements for transportation for purposes of prostitution. I think we've seen that with the male sex workers who've already testified. So that part of the case is almost done.

COATES: We'll see about any, obviously, corroborating documents to support the payment structure. A lot of it was in cash as well. We also heard yesterday from forensic psychologist and clinical psychologist, Dr. Dawn Hughes, who also testified at the Johnny Depp- Amber Heard trial. What was your assessment of her testimony?

CHEW: I did not think her testimony was very persuasive. That's my personal opinion. For the same reason, I don't think it was persuasive in the -- in the trial you just referred to, in the Depp trial, because she had no direct experience. No -- she did not examine Cassie Ventura. And I think that's a real weakness in her case because she's opining about someone she has never met and she has never examined. So, I think -- I think that hurts her. I think the cross-examination of her was effective, establishing that she had always and only represented alleged victims, never had taken the other side. I think that also shows that she was biased and had the appearance of a hired gun, whether that was true or not.

COATES: Important to think about how they would assess it. Early on, you suggested that Diddy may need to testify. Should he?

CHEW: Well, the common wisdom, the standard wisdom, as you know, is not to testify, particularly where is here. He has 80 civil suits against him. All of that comes in in cross-examination.

However, I will be in the minority and say he may testify because I think just some of the testimony that's come in, I think the video that we've all seen is -- is so damaging. I think he may want to take a chance and explain how sorry he is, how contrite he is, how he was a different person then.

This is many years ago. So, I -- I think that -- that could help, but that's going to be an ultimate decision. I also think that the outcome of this case may turn on closing arguments and how each side, prosecution and defense, frames this issue.

COATES: We had a little bit of a preview of what a potential testimony from Diddy might look like. He issued an apology of sorts following the disclosure of that hotel video. Listen to what he had to say, a piece of it.

(BEGIN VIDEO CLIP)

SEAN "DIDDY" COMBS, RAPPER, RECORD PRODUCER, RECORD EXECUTIVE: My behavior on that video is inexcusable. I take full responsibility for my actions in that video. Disgusted. I was disgusted then when I did it. I'm disgusted now, but I'm committed to be a better man each and every day. I'm not asking for forgiveness. I'm truly sorry.

(END VIDEO CLIP)

COATES: Say, he strikes that same tone in his testimony, will it be enough?

CHEW: It might be. I -- I think he's got to be -- some of those words seemed a little practiced. I -- others have criticized the apology. I don't think it was that bad. I think he's going to have to be more expansive.

And there's always -- how much do you actually look into the eyes of the jurors? It's generally not too good an idea to do that. Some jurors find it intimidating. But just a little bit of a look over there might be helpful.

I think he has to be more fulsome in his explanation and talk more about Cassie and how he -- it's not just what he's doing and taking responsibility, it's what he did to her and how he recognizes that.

COATES: Have to distinguish between being a domestic abuser and a racketeer as well. Right? Ben Chew, great to have you.

CHEW: Thank you so much.

COATES: The prosecution is taking through its witness list with many more still to go. So what parts of the story do they still need to tell, and which witnesses might help them do that? My next guest might have some idea. She is the filmmaker behind "The Fall of Diddy" documentary featuring major interviews with all the key players, and she is standing by with her perspective, next.

[23:45:04]

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COATES: Sean "Diddy" Combs faces a lifetime behind bars if he is convicted. It's a far cry from his lavish life in the spotlight. But his celebrity status also left behind a trail of evidence for investigators and the public.

[23:50:00]

The discovery I.D. docuseries, "The Fall of Diddy," highlighting some of those allegations months before his trial began. Some stories sound eerily similar to the testimony that has been heard in court.

(BEGIN VIDEO CLIP)

ROGER BONDS, FORMER BODYGUARD FOR SEAN "DIDDY" COMBS: We went to a big party on sunset. And when I was waiting outside, I've seen Cassie come out first, and then I've seen Puff come out, and he was walking fast. And then all of a sudden, I just seen him out of nowhere just punch her. And then they started fighting there. I tried to, at first, say, get inside the car. Are you crazy? Are you crazy? And then he said, no, no, no, and he started kicking her.

(END VIDEO CLIP)

COATES: Now Combs has denied all the allegations and has pleaded not guilty to the federal charges. Joining me now, the co-director of "The Fall of Diddy," Yoruba Richen. So glad that you are here.

And this has really been a compelling moment, to reflect back on what your docuseries has said and, of course, the testimony that has emerged at trial. You've heard from some of Combs's employees and accusers. So, you've heard some of these stories before. But what has stood out to you nearly now two weeks into trial testimony?

YORUBA RICHEN, DIRECTOR, "THE FALL OF DIDDY": Well, thank you for -- for having me, Laura. I think what is -- what we're seeing, you know, with this testimony at the trial is really filling in a lot of information and details that we didn't have. I mean, this is the first time we've had Cassie speak at length after her law -- filing the lawsuit, and it's definitely filling in more information about her experiences with Combs in that relationship. This is the first time we've heard Kid Cudi speak.

COATES: Uh-hmm.

RICHEN: So, it is filling in a lot of the things that we heard that people alleged, but hearing it from, you know, from the -- the mouths of the folks who experienced these events with Combs.

COATES: You know, you mentioned before just how afraid people were in the documentary, afraid to come forward. Are you surprised at how many former staff members of Combs have even testified so far, let alone people who allegedly had these sexual encounters?

RICHEN: Well, what we found in making the documentary is that as more of these events unfolded, you know, Cassie's lawsuit, the raid of Combs's house, the video of him assaulting Cassie, the apology, the arrest, that -- that prompted more and more people to come forward.

It happened in our film. We had more people contact us and wanting to talk because seeing, you know, these events unfold, I think there was a safety in numbers that folks felt, and there was a desire to be part of holding Combs accountable.

COATES: You were actually -- the timeline is important here, I think. You were actually filming when CNN obtained the 2016 hotel security video that shows Combs dragging and kicking Ventura. What did you think of her testimony last week as you talked about how it filled in some of those gaps from her perspective?

RICHEN: Well, I mean, when we first saw that video, when -- when -- when the world first saw that video, it was shocking. It's one of the, you know, most shocking pieces of footage I've ever seen. And hearing the testimony, it -- she is, you know, again, saying in her own words what happened. And, again, it's shocking and it's upsetting.

And I -- I have to say, Cassie and the other folks who've come forward with these allegations, you know, are really showing a bravery to -- to testify and to, you know, attempt to have Combs be held accountable. It's very hard, and it's very courageous of these folks to do so, as they did so in our film, and as we're seeing in court.

COATES: Thank you for not underestimating the bravery of anyone who comes forward when they have been victimized. You know, you spoke to several people who had their own stories of alleged attacks from Combs, and he has denied all of them. But you said there have been signs for decades. Why do you think he was able to hide this for so long? I mean, people talk about inner circles, but this was outer enablers if that's the case.

RICHEN: Well, you know, I think we've seen in our society, in our culture that people who have been -- who have had, you know, abusive behavior or alleged abusive behavior for many, many years are able through their power, through their -- through intimidation are able to skate accountability.

[23:55:03]

Combs is not the only one. And I think that that is something that, you know, that we have seen. And I think it is money and power and fear that allows people to do that. Celebrity as well, whether it's, you know, celebrity in culture, in politics, what have you. So, I think this is something that is, you know, endemic in our culture.

COATES: What you describe really confirms that this trial is more than just about the individual players involved. Yoruba Richen, thank you so much.

RICHEN: Thank you for having me, Laura.

COATES: You can listen to much of our trial coverage on my brand-new CNN podcast, "Trial by Jury." You can listen to -- listen to it on cnn.com or wherever you get your podcast.

I want to thank you all for watching. "Anderson Cooper 360" is next.

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