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Bad Rap: The Case Against Diddy

The Trial: Prosecutors Go for the Big Fish

Fri, 23 May 2025

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Brian recaps key moments in court this week, including Kid Cudi taking the stand. Then, a conversation with former prosecutor Moira Penza who won a conviction in the high profile RICO and sex trafficking case against Keith Raniere of NXIVM. Diddy faces those charges as well, and two of the defense attorneys Penza went up against in that 2019 trial are now representing him. If you have questions about the case, leave us a voicemail at 929-388-1249. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Chapter 1: What key moments occurred in court this week?

38.067 - 55.072 Brian Buckmeyer

We heard from two special agents from Homeland Security Investigations, two former assistants who worked for Sean Combs, a makeup artist, and perhaps the most anticipated witness this week, Scott Muscadie, better known as rapper Kid Cudi, who once dated Cassie Ventura.

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Chapter 2: Who took the stand during the trial?

56.519 - 80.61 Brian Buckmeyer

In her civil lawsuit, Cassie alleged that Combs threatened to blow up Kid Cudi's car after finding out that she and Kid Cudi were dating. Well, Thursday, we finally heard Kid Cudi's version of that story. Kid Cudi walked towards the witness stand, wearing a black leather jacket opened with a white t-shirt underneath, blue jeans, and crisp white sneakers.

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Chapter 3: What were Kid Cudi's allegations against Sean Combs?

81.311 - 104.936 Brian Buckmeyer

A cross earring dangling from his right ear. He testified about a break-in at his home in December of 2011. While he was with Cassie, he says he got a call from an assistant to Sean Combs, who allegedly told him Combs was in his house. Kid Cudi told the jury he returned home to find his gifts that he had bought for his family had been opened and its dog locked in the bathroom.

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106.221 - 129.326 Brian Buckmeyer

After the New Year, he testified he got a call that his Porsche was on fire in his driveway. Jurors saw photos of the blackened interior and the charred, melted driver's seat. Kid Cudi said a Molotov cocktail was dropped into the car through a hole cut in the roof. Arson is one of the underlying acts included in the racketeering conspiracy count Combs is facing.

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130.046 - 141.336 Brian Buckmeyer

And Cassie Ventura previously testified that Combs had threatened to have Kid Cudi's car blown up. Kid Cudi testified that he reached out to Sean Combs to kind of squash the beef.

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142.257 - 162.57 Brian Buckmeyer

He met Combs at the Soho House of Los Angeles, where he walked into a room with just Combs standing there, staring out of a window with his arms behind his back, looking like, as Kid Cudi testified, some kind of a Marvel supervillain. That line got a laugh from the jury.

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163.536 - 189.726 Brian Buckmeyer

Although Cassie testified she started seeing Kid Cudi when she and Combs' relationship was in a rough patch, Kid Cudi testified that Cassie told him they had been split up. On cross-examination, the defense said both Kid Cudi and Combs were played by the same woman. The person who played you, the person who played Sean, was Miss Ventura, true? One of the lawyers asked. Yeah, Kid Cudi replied.

194.198 - 208.296 Brian Buckmeyer

And this week, the jury saw other photos too, including pictures of baby oil, lingerie, platform heels, and sex toys. You'll recall Diddy's Los Angeles and Miami homes were raided by federal agents back in 2024.

209.898 - 230.02 Brian Buckmeyer

Special Agent Gerard Gannon testified that the feds recovered the parts of two AR-15 assault-style rifles with defaced serial numbers only feet from where Combs allegedly stored supplies for freak-offs. Prosecutors have argued that the threat of violence allowed Combs to coerce his alleged victims to participate in freak-offs.

231.221 - 248.679 Brian Buckmeyer

Jurors also saw baggies of colorful pills and other drugs allegedly found in Combs' home, including marijuana, powders, and other drugs that prosecutors have alleged were used to make participants compliant during freak-offs and would allow them to perform well past the point of exhaustion.

250.751 - 275.531 Brian Buckmeyer

Thursday afternoon, a makeup artist who worked with Diddy and Cassie testified that she saw Cassie with a swollen eye and busted lip and knots on her head after the Grammys in 2010. Altogether, this week, it felt like the prosecution was really beginning to build support for its racketeering conspiracy charges. This is Bad Rap, the case against Diddy.

Chapter 4: How does the prosecution plan to prove sex trafficking?

1136.303 - 1144.33 Brian Buckmeyer

So sometimes people ask me in just a layperson's term, and so I'm going to ask you in this term. Sure. Is it sometimes that you're just going after the big fish and you let the little fish go?

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1144.35 - 1167.445 Moira Penza

I think that's totally fair. And I think that's the way that the system should work. I think that prosecutorial discretion is a very important part of the system. And certainly there can be cases where for a variety of reasons, maybe because somebody was such a victim him or herself that you choose not to prosecute them.

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1172.029 - 1181.356 Brian Buckmeyer

Just ahead, former prosecutor Moira Penza has faced some of Combs' defense team in court before. And she says they're making some new moves in the Combs trial.

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1281.529 - 1303.915 Brian Buckmeyer

And I'm back with Moira Penza, a former federal prosecutor who's brought charges similar to what Sean Combs is facing. Perhaps her most high-profile case was the prosecution of Keith Raniere, the former NXIVM leader who was convicted of crimes including racketeering and sex trafficking in 2019. I asked Moira if she sees any parallels between the two cases.

Chapter 5: What is the significance of RICO charges in this case?

1494.614 - 1517.307 Moira Penza

In the Naxiom case, there was a little bit of that. And of course, the sex crimes themselves are inherently violent. But this sort of brutal physical violence is something that we didn't have in my case, but that you do have in this case and that I think is very powerful evidence for the prosecutors.

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1518.2 - 1535.39 Brian Buckmeyer

You've got a little bit of inside baseball here because you've gone up against Mark Ignifilo and Tenny Garagos. And now the SDNY is going up against who I would describe as the lead defense attorneys at Sean Combs. So what can we expect of their style? What can we expect of the way they're going to cross-examine?

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1535.79 - 1542.954 Brian Buckmeyer

What can we expect of the closing arguments that the defense is likely going to bring up since you know their style of defense?

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1544.275 - 1561.955 Moira Penza

Mark and Tenny were the team in the NXIVM case, so I know them well. Ms. Garagos did not have as much of a stand-up role during the NXIVM trial. I certainly think she's a talented lawyer. And I do think optically it was...

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1562.996 - 1594.562 Moira Penza

a good decision on the part of the defense team to have a young woman who was a contemporary of the prosecution team standing up and showing that she was on the defendant's side and advocating for the defendant. So I think to Mark and Tenny's credit, I don't think they're necessarily following the same playbook that I saw in their defense of Keith Raniere.

1594.722 - 1621.731 Moira Penza

And I think that reflects, you know, probably their own evolution in how to defend these cases. But also, I think likely, I think Mr. Combs is maybe more willing to allow them to take certain approaches like... accepting responsibility for being a bad boyfriend for domestic abuse.

1622.271 - 1643.979 Moira Penza

So I think right now, where I think we're going to see closing arguments go is really a bookend of what we saw in opening. I think we're going to see the defense say, We've heard a lot of stuff you might not like, jury, but it's not the crimes that the government has charged.

1644.359 - 1656.905 Moira Penza

And I think in that respect, it will be a little bit more matter of fact than we might have seen in the NXIVM case, where I think Mark...

1657.885 - 1685.784 Moira Penza

made more of an effort to try and paint Keith Raniere as actually a good man with good intentions, as opposed to here where I think they realize it will be a more effective strategy to admit that Mr. Combs is a deeply flawed individual and just try and get the jury to stay focused on the narrow issue of, are these crimes actually proven?

Chapter 6: How is the defense strategy shaping up?

1794.734 - 1826.122 Moira Penza

And what Dr. Hughes does is not talking about the specifics of the case at all can explain why this sort of victim behavior and the psychology of it and why we can see that and put it into terms that are understandable for a jury. And then the jury can apply what they've heard from Dr. Hughes to what they've heard the victim say. And then it may be a lot more understandable.

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1826.562 - 1852.963 Moira Penza

So, for example, Dr. Hughes talks about the fact that there's often love in these long-term relationships where there's abuse. But there's these trauma bonds that keep people coming back, even in situations where a lay person who, you know, thankfully has not experienced this sort of behavior thinks, why didn't she just leave? The door was open. Yeah. She had family. She could have gotten help.

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1853.583 - 1876.111 Moira Penza

And Dr. Cuse can explain how difficult that can be in a situation where you've been abused repeatedly, especially where you have an individual who is extremely famous, who has enormous power over your career. And that can be really helpful for the jury in answering some questions that they might have.

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1876.587 - 1889.331 Brian Buckmeyer

So the interesting thing that I found with this case, which also happened in Keith Raniere's case, was that the defense had the argument of some of this was consensual or all of this was consensual as a way of defending their case.

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1890.632 - 1900.175 Brian Buckmeyer

What kind of difficulties does that create for the government in terms of trying to prove their case that either consent didn't happen or it doesn't matter in the context of these allegations?

1901.812 - 1931.918 Moira Penza

I don't think that consent is a real challenge in this case because of the level of physical violence that you have and because of the coercive elements, the threats of blackmail. It's something that is a challenge for the government, but certainly something that can be overcome. And I think it's just something for the government to address head on. But this isn't a he said, she said case.

1931.998 - 1955.231 Moira Penza

It's really going to come down to the legal standard. I think the government is going to be able to show how... Regardless of what Ms. Ventura may have said on any occasion or what the text messages say, that the elements of sex trafficking are met, that's what we're going to hear the government say about these alleged crimes.

1955.791 - 1965.337 Brian Buckmeyer

How do you prepare alleged victims to testify in court, considering all of what's going to happen in the direct examination, showing up to court, and especially the cross-examination?

1966.325 - 1991.659 Moira Penza

I think that's one of the most challenging aspects of being a prosecutor because you are really asking these alleged victims to relive some of the most traumatizing events of their life. And What I like to do is remind our victims back when I was a prosecutor that this individual doesn't have power over you anymore.

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