• If you’re a certain age, Sean’ Diddy’ Combs was inescapable during some really formative years of your music-listening habits. The entertainment mogul and producer showed up in music videos, hosted a reality show, and had a clothing line. His label Bad Boy Records helped launch the careers of iconic names in Hip-Hop and R&B, like Mary J. Blige, Usher and Notorious B.I.G. Now, he’s standing trial on federal sex trafficking and racketeering charges, and faces the possibility of spending the rest of his life in prison, if convicted. Anne Branigin, a staff writer for The Washington Post has been covering the trial from the Manhattan courthouse. She joins us to talk about the latest developments in the case and what’s still to come.
• And in headlines: The U.S. government officially accepted a $400 million Boeing 747 from Qatar, President Donald Trump lectured the president of South Africa about a ‘white genocide’ in his country that’s not happening, and Virginia Democratic Rep. Gerry Connolly passed away at 75 after a battle with esophageal cancer.

• Follow Anne for more coverage of the trial – www.washingtonpost.com/people/anne-branigin/
• Subscribe to the What A Day Newsletter – https://tinyurl.com/3kk4nyz8
• What A Day – YouTube – https://www.youtube.com/@whatadaypodcast

Follow us on Instagram – https://www.instagram.com/crookedmedia/

 

TRANSCRIPT

 

Jane Coaston: It’s Thursday, May 22nd. I’m Jane Coaston, and this is What a Day, the show asking if Elon Musk knows what it means to step away from politics. Sure, he said he’d back off from political funding, but he was on Capitol Hill on Wednesday, and President Donald Trump said he was behind the Afrikaner’s refugee plan. 

 

[clip of President Donald Trump] I don’t want to get Elon involved, that’s all I have to do, get him into another thing. But Elon happens to be from South Africa, this is what Elon wanted. 

 

Jane Coaston: This is what Elon wanted. Maybe step away means something different for chainsaw enthusiasts. [music break] On today’s show, President Donald Trump, I mean, excuse me, I need to correct myself, the United States government officially accepts a 400 million dollar Qatari Boeing 747. And Trump lectures the President of South Africa with fake news about a white genocide in South Africa. But first, we’re taking a break from the literal and figurative hot mess that is our nation’s capital and the knuckleheads running the government to talk about the federal sex trafficking and racketeering trial of Sean Combs, AKA Diddy. And a warning to our listeners, we’re gonna talk a lot about sex, abuse, and violence in this episode. Some people might find the subject difficult, or if you’ve got kids around you, maybe this isn’t the best time to listen. If you’re of a certain age, as in you remember watching TRL on MTV, the music mogul and producer was a kind of inescapable phenomenon during some really formative years of your music listening habits. He showed up in music videos. He was the host of the reality show, Making the Band, about creating a boy band, and then a girl band. He had a clothing line, Sean John. His label, Bad Boy Records, helped launch the careers of iconic names in hip-hop and R&B, like Janelle Monae, Mary J. Blige, Usher, and Notorious B.I.G. Heck, we even heard about his celebrity-strewn white parties. And now, he faces the possibility of spending the rest of his life in prison. Federal prosecutors allege Diddy, quote, “abused, threatened, and coerced women and others around him to fulfill his sexual desires, protect his reputation, and conceal his conduct.” They also say he created a, quote, “criminal enterprise through his business empire in order to make that possible.” It’s a big case. The judge overseeing it says the trial could take eight weeks. We’re at the tail end of week two of testimony, which means there’s still a long way to go and a lot of evidence still to come. On Wednesday, jurors heard from Diddy’s former assistant who described obtaining drugs for the rap producer. They also heard from a psychologist who discussed the impact of domestic violence and sexual abuse on victims. That tied into earlier testimony from the singer, Cassandra Ventura, Diddy’s former longtime girlfriend, who alleged in detailed graphic testimony the ways she says Diddy was both sexually and physically abusive. This isn’t just a story about celebrity. It’s about the wielding of power and fame as a cudgel, one aimed particularly at young women. So to discuss the Diddy trial further, I talked to Anne Branigin, staff writer for the Washington Post Style Section. She’s been covering the trial from the Manhattan Courthouse where it’s taking place. Anne, welcome to What a Day. 

 

Anne Branigin: Hi, thank you for having me. 

 

Jane Coaston: So this trial is about to wrap up its second week of testimony. What’s the mood been like in the courthouse? 

 

Anne Branigin: The mood has been pretty intense, and we’re going through a lot of witnesses very quickly. Um. There hasn’t been a boring day so far in this trial, which is pretty, I think, incredible. 

 

Jane Coaston: Yeah, no, having covered legal proceedings before, that’s kind of surprising. Now, the primary witness in this case is a singer, Cassandra Ventura, better known as Cassie. She dated Combs for about a decade and her testimony about the alleged abuse Diddy inflicted on her was horrible and graphic. Can you walk us through some of the big moments from her four days of testimony? 

 

Anne Branigin: Right well, we got her testimony very early in the trial, which is kind of unusual to have a star witness go so early when, you know, the side is presenting their case, in this case, the government, right? Um. But she was very pregnant, which is part of the reason why she took the stand so early. And so we really saw her lay out their 11-year relationship, going from meeting Sean Combs and how enamored she was with him and the lifestyle that he was introducing her to. You know, she talked about the honeymoon period at the beginning of the relationship, but she also delved into, in quite graphic detail, some of the things that would come later. And so she alleges that she was forced to participate in freak-offs. And these are the sex parties that have been talked about a lot at this point. You know we first heard about them in the lawsuit that she filed in 2023. And she also detailed a lot of the physical abuse that she says she experienced at the hands of Sean Combs. 

 

Jane Coaston: How did Diddy’s defense team try to poke holes in her testimony? 

 

Anne Branigin: Mainly through text messages. So as you can imagine, over the course of an 11 year off and on relationship, there were a lot of messages exchanged between these two. And they really homed in on a few messages, you know, ones where Sean Combs appeared to be kind of deferring to Cassie Ventura in terms of, you now, kind of following her lead on whether she wanted to to do a freak-off that evening or that week. There were texts that they shared in which she expressed how much she enjoyed them, right? And to be clear, just to place this in time, these are texts that she sent when she would have been about you know 22, 23. So well over a decade ago at this point. So that’s been the defense’s kind of tactic in terms of chipping away a really essential part of this story, which is the idea that there was force and coercion. 

 

Jane Coaston: And without getting into too much graphic detail, can you tell us more about these freak offs and how the prosecution says they play into this case? 

 

Anne Branigin: Well baby oil has been mentioned just about every day of this trial so far. Um. So what we know about the freak-offs is that these were held in hotels, that they involved Cassie Ventura, some other alleged female victims from whom we will hear later on in the trial, and that they typically involved a male escort, right, who would participate specifically with the woman while Sean Combs would watch in a corner. And the important detail here, the prosecution believes, is how much he directed these events and how they were really tailored to his preferences. So that’s where the baby oil comes in. He apparently would, with regularity, tell them to slather more and more baby oil on themselves. He was very um involved in terms of the lighting of these rooms you know, he had very specific demands in terms of snacks and drugs provided. So that’s what the prosecution is laying out to kind of corroborate the argument that Combs is really driving these these sex acts. 

 

Jane Coaston: And there was also video footage from a hotel security camera played in court, CNN had obtained and aired the video last year it is horrifying it shows Diddy grab, shove, drag, and kick Cassie while they were at a hotel in 2016. That seems to be especially damning in so many ways but the case isn’t specifically about abuse it’s about sex trafficking and racketeering so how has the government been making its case for those charges that are bigger in scope than hortifying domestic violence and sex acts?

 

Anne Branigin: I’m so glad you brought that up, right, and because that’s a big part of what the defense’s position is, right? They are not dodging the fact that physical abuse happened. They are not dodging the fact that Combs did assault Cassie in the hotel that day. But their line is that this is not a domestic violence trial. It is, as you said, a sex trafficking and racketeering trial. So, essential to the sex trafficking charge is trying to establish that you took part in a commercial sex act under force, fraud, or coercion. And so that’s why we see the emphasis on physical abuse, right, and why we have other witnesses corroborating the fact that Sean Combs was violent, that he would get violent with little provocation. It’s because they want to establish that these are the reasons why Cassie Ventura might have participated in sex acts that she did not actually want to participate in. Another [?]–

 

Jane Coaston: And would be texting in a way that might seem like she was into it, but she may have been coerced into doing so and feel frightened. 

 

Anne Branigin: Exactly. And another element that comes up, too, is the fact that these acts were videotaped. And something that she said in her testimony was that that would be used as sort of leverage against her as blackmail, so that if she left him, he would threaten to release those videos. Something that also came up is the amount of financial control he had over her. And that’s not just in the fact that he owned and, you know, paid the rent on her homes, but that Combs was her boss, right? She was a bad boy artist and bad boy is the label that he founded. And so her career was really in his hands. And so those are the things that the prosecution has stressed in order to try to make those connections. 

 

Jane Coaston: Cassie wrapped her testimony on Friday. Who are some of the other notable witnesses we’ve seen at this point in the trial? 

 

Anne Branigin: We have seen some very colorful testimony, I’ll say. So we’ve heard from law enforcement agents. We’ve um heard from a couple of the men who participated in these sex acts, you know, a male exotic dancer who goes by the nickname, the Punisher, and yes. 

 

Jane Coaston: Okay. 

 

Anne Branigin: Um, we also heard from Cassie Ventura’s mother, who shared to me some really striking testimony about how Combs demanded $20,000 from her because he said that was money he spent on Cassie Ventura and he wanted to be reimbursed because she had been with another man. 

 

Jane Coaston: Yeah, I read a little bit about that testimony and, you know, the person she had been with was the rapper Kid Cudi, whose real name is Scott Mascuti, who’s expected to testify today. He briefly dated Cassie while she was involved with Diddy and his car exploded after, he alleges, a heated argument with Combs in which Combs threatened to blow up his car. What can we expect from his testimony? 

 

Anne Branigin: So he’s definitely gonna be asked about that event because it’s mentioned in the federal indictment, you know part of the racketeering charge is arson. And arson relates directly back to that very specific act of his car exploding. So he won’t be on the stand for very long today because they have a lengthy list of witnesses that they wanna get through um before the Memorial Day weekend break. But we can definitely expect him to give us some more detail about what happened there. 

 

Jane Coaston: As someone who’s been catching updates on TV and in the news, the evidence presented so far would seem to be especially damning for Diddy, one of the most influential people in the music industry. I was talking to one of my colleagues about how like, if you’re around our age, there was a period of us being teenagers where like he was kind of inescapable, like either through his fashion or his music, or just like being a famous person. Even if he’s acquitted of these charges, what kind of reputational damage has this trial inflicted? 

 

Anne Branigin: I’ve been thinking about that a lot because, you know, the jury has a job of looking at this very sort of narrow and specific scope of the alleged crimes of behavior. But this has fundamentally, I think, reshaped his legacy in a way that I think we’re still going to be reckoning with once the trial is done, no matter what the outcome is, right? We know a lot about this man now that we perhaps did not want to know. And I mean, like you, you know, his music was a big part of my childhood. And maybe it’s because the news is everywhere right now. Maybe it’s of the level of detail that we know. But it’s hard to listen to that music now without thinking about some of these things. 

 

Jane Coaston: Anne, thank you so much for joining me 

 

Anne Branigin: Thank you for having me, I really appreciate it. 

 

Jane Coaston: That was my conversation with Anne Branigin, who’s been covering Diddy’s trial for the Washington Post. We’ll link to her coverage in our show notes. We’ll get to more of the news in a moment, but if you like the show, make sure to subscribe, leave a five-star review on Apple Podcasts, watch us on YouTube, and share with your friends. More to come after some ads. [music break]

 

[AD BREAK]

 

Jane Coaston: Here’s what else we’re following today. 

 

[sung] Headlines. 

 

[clip of President Donald Trump] What a group of golfers South Africa’s had. 

 

[clip of Cyril Ramaphosa] Yes, yes. 

 

[clip of President Donald Trump] I don’t know. There must be something in the water, right? 

 

[clip of Cyril Ramaphosa] Yes. 

 

[clip of President Donald Trump] Something good? These two guys are unbelievable. 

 

[clip of Cyril Ramaphosa] It’s the water, the water–

 

Jane Coaston: President Donald Trump met with South African President Cyril Ramaphosa in the Oval Office on Wednesday. After the two initially exchanged pleasantries and discussed golf, Ramaphosa brought two South African golf legends to the meeting. Smart. President Trump moved on to another favorite topic of his, misinformation. 

 

[clip of President Donald Trump] Look, these are articles over the last few days. A death of people. Death, death, death. Horrible death. White South Africans are fleeing because of the violence and racist laws. 

 

Jane Coaston: More specifically, Trump harped on the idea that there is a so-called white genocide happening in South Africa. This is false. A South African judge dismissed this in February as non-existent. Just weeks earlier, President Trump issued an executive action allowing Afrikaners to resettle in the U.S. So far, 59 white Afrikaners have arrived in the US as refugees. When a reporter from NBC News asked why it was appropriate for the United States to take in white Afrikaner refugees when other groups like Afghans, Venezuelans, and Haitians have had their protective status revoked, Trump called the network truly fake news. Later on in the meeting, he called for an investigation into NBC’s parent company, Comcast. Free speech is alive and well in the Trump White House. At another point during the meeting the lights in the Oval Office dimmed as Trump played a video purporting to show violence against white Afrikaners and mass burial sites for white farmers. President Ramaphosa wondered aloud where exactly the mass graves were located. 

 

[clip of President Donald Trump] Those people were all killed. 

 

[clip of Cyril Ramaphosa] Have they told you where that is, Mr. President? 

 

[clip of President Donald Trump] No. 

 

[clip of Cyril Ramaphosa] I’d like to know where that is, because this I’ve never seen. 

 

Jane Coaston: After pausing, Trump answered, it’s in South Africa, but according to Barron’s, one of the photos depicted a grave located in the Democratic Republic of Congo, which is a different country. The Trump administration received another judicial rebuke Wednesday, another one. US District Judge Brian E. Murphy in Boston called an emergency meeting to discuss reports that immigrants were being sent to South Sudan in violation of a previous court order. Judge Murphy cited that the previous order barred immigrants from being deported to countries they’re not from without a meaningful opportunity to object on the basis of safety. He warned everyone involved an illegal deportation risks criminal contempt. According to the Council on Foreign Relations, South Sudan is suffering from one of the worst humanitarian crises in the world. Department of Homeland Security officials said eight immigrants were deported Tuesday. They claim that the migrants, who are from Cuba, Laos, Mexico, Myanmar, Vietnam and South Sudan, are criminals. During a press briefing Wednesday, DHS spokesperson Tricia McLaughlin slammed what she calls activist judges. 

 

[clip of Tricia McLaughlin] It is absolutely absurd for a district judge to try to dictate the foreign policy and national security of the United States of America. 

 

Jane Coaston: Well I think it’s absolutely absurd for the United States government to send Laotians and Mexicans to South Sudan, so agree to disagree, Trish. Anyway, McLaughlin would not confirm a final destination for the migrants. 

 

[clip of Hakeem Jeffries] Thank you so much, and thank you so much for the moment of silence and the kind words of remembrance on behalf of our dear colleague, Gerry Connolly. 

 

Jane Coaston: House Minority Leader Hakeem Jeffries paid homage to his late colleague, Democratic Representative Gerry Connolly. Connolly had represented Virginia’s 11th district since 2009. He died on Wednesday after battling esophageal cancer. He was 75. Connolly was widely known for his fiery spirit, along with his business and infrastructure efforts in northern Virginia. Over the course of his career, Connolly expanded the Metro’s silver line from the DC suburbs to Dulles Airport. Here he is during its opening ceremony 10 years ago. 

 

[clip of Gerry Connolly] This is going to transform this court into something a lot more livable, a lot environmentally friendly, a lot commercially successful, and is gonna make a difference to generations. 

 

Jane Coaston: Late last year, Connolly announced his illness and said he would fight his disease. In April, however, he announced that his treatment had been unsuccessful, that he would not seek reelection in 2026, and that he step down from his leadership position on the House Oversight Committee. Last December, one month after announcing his cancer, Connolly beat out Representative Alexandria Ocasio-Cortez to become the ranking member of the House Oversight Committee. Connolly’s death is the third of a Democratic lawmaker since November’s elections. Defense Secretary Pete Hegseth accepted a Boeing 747 from Qatar on Wednesday, which is a weird thing to say, right? In a statement, Chief Pentagon spokesman Sean Parnell said the Secretary complied with all federal rules and regulations in accepting the jet. Parnell also said that the Department of Defense will make sure it’s safe for a President of the United States to fly in, to transport the President. Some Republicans and Democrats alike have criticized the gift, saying accepting it violates the Constitution. But President Trump has continued to defend the gift because of course he has. In a Truth Social post last week, Trump said, quote, “Why should our military, and therefore our taxpayers, be forced to pay hundreds of millions of dollars when they can get it for free?” Ah yes, there’s the businessmen we know. And taxpayers will be paying to refurbish the plane, so really it’s only free for one person. Trump was asked about the jet during his Oval Office meeting with South African President Ramaphosa. Ramaphosa piped in. 

 

[clip of Cyril Ramaphosa] I’m sorry I don’t have a plane to give you. 

 

[clip of President Donald Trump] I wish you did, I’d take it. [laughter] I would take it. If your country offered the United States Air Force a plane, I would take it.

 

Jane Coaston: Of course you would. Shocking, but not surprising. And that’s the news. [music break] Before we go, Project 2025 is no longer a warning, it’s a reality. Four months into Trump’s second term, Republicans have already begun executing their 900 plus page plan to transform America into a Christian nationalist state. We’re seeing it in real time, attacks on bodily autonomy, the targeting of immigrants, the erasure of history, and cuts to programs millions rely on. On today’s episode of Assembly Required, Stacey Abrams sits down with Atlantic staff writer, David A. Graham, author of The Project, How Project 2025 is reshaping America. To unpack the radical ideology and what we can do to fight back before it’s too late. Tune in to this important episode of Assembly Required on YouTube or listen wherever you get your podcasts. [music break] That’s all for today. If you like the show, make sure you subscribe, leave a review, let me be the liberal Joe Rogan, and tell your friends to listen. And if you’re into reading and not just about how seriously, I also can fill three hours with MMA, World War II, and discussions about aliens, like me, What a Day is also a nightly newsletter. Check it out and subscribe at Crooked.com/subscribe. I’m Jane Coaston. And alternatively, we could come up with additional ideas besides that one. [music break] What a Day is a production of Crooked Media. It’s recorded and mixed by Desmond Taylor. Our associate producers are Raven Yamamoto and Emily Fohr. Our producer is Michell Eloy. We had production help today from Johanna Case, Joseph Dutra, Greg Walters, and Julia Claire. Our senior producer is Erica Morrison, and our executive producer is Adriene Hill. Our theme music is by Colin Gilliard and Kashaka. Our production staff is proudly unionized with the Writers Guild of America East. [music break]

 

[AD BREAK]