Sean “Diddy” Combs is facing five federal charges—including racketeering conspiracy, sex trafficking, and transportation to engage in prostitution—accusations that could carry a life sentence if he’s convicted.
His trial began last week in New York, offering an early look at how each side plans to argue a case expected to span two months. Prosecutors allege that Combs led a criminal enterprise that used drugs, violence, and manipulation to coerce women into sex acts, often across state lines, with his staff allegedly coordinating the travel and covering the expenses.
Week one centered on testimony from Cassie Ventura, Combs’ longtime ex-girlfriend, who described a relationship shaped by coercive control, physical abuse, and orchestrated sex acts known as “Freak Offs.”
The defense countered by portraying the relationship as consensual. They acknowledged Combs may have been violent at times, but argued that those incidents fall short of sex trafficking or racketeering. They also questioned Ventura’s credibility and motivations, pointing to her $20 million civil settlement.
Below, we broke down everything that happened during week one of the trial—day by day. Find recaps of testimony that reveal previously unknown details about “Freak Offs,” the infamous 2016 hotel surveillance video, Kid Cudi’s involvement, and the relationship between Ventura and Combs.
Day One: Opening Arguments and Eyewitnesses
The case centers around Combs’ alleged role in a sex trafficking operation involving at least three women—Cassie Ventura, “Jane,” and a former employee known as “Mia.” Jury selection concluded on May 12, finalizing a panel of 12 jurors and 6 alternates. While some acknowledged seeing media coverage or the 2016 surveillance footage of Combs assaulting Ventura, all affirmed they could remain impartial.
The Defense Pushes Back
Defense attorney Teny Geragos didn’t deny Combs’ past violence but argued the sex trafficking charges are unfounded. She claimed the relationships were consensual, describing Combs as a “complicated man” with an unconventional lifestyle, not a criminal.
“Yes, he loved baby oil,” she told jurors. “Is that a federal crime? No.”
First Witnesses Take the Stand
The prosecution’s first witness, hotel security guard Israel Florez, described seeing Ventura shortly after the 2016 hotel incident—visibly shaken with a swollen eye, allegedly trying to flee. He claimed Combs offered him a cash bribe to stay silent, though under cross-examination, he admitted some details, like the eye injury, weren’t in his original report.
Male escort Daniel Phillip followed, testifying he was paid thousands between 2012 and 2014 to have sex with Ventura while Combs watched. What started consensually, he said, turned abusive. He recounted Combs allegedly dragging Ventura by her hair and screaming at her before slapping her.
“It was going through my mind that if I tried to do something, I might lose my life,” Phillip said. During cross-examination, the defense tried to portray the acts as consensual. Phillip confirmed Ventura paid him and was neither drunk nor high, but when asked if she was fully in control of her actions, he replied, “I cannot say that.”
Day Two: Cassie Takes the Stand
On the second day of the trial, Cassie Ventura began her highly anticipated testimony, laying out years of alleged abuse, control, and coercion by Sean “Diddy” Combs, with whom she had an on-and-off relationship from 2006 to 2018.
Before testimony began, Combs’ legal team attempted to have Ventura seated before the jury entered, arguing her visible pregnancy could draw sympathy. The judge denied the motion. They also asked to restrict her husband, Alex Fine, from the courtroom due to past threats directed at Combs. That motion was also denied, with the exception of any rape-related testimony.
A Relationship Built on Control
Ventura testified that their relationship started platonically when she was 19 and became romantic after her 21st birthday. At the time, Combs was 17 years older and held total control over her career. “He was a fun guy who also happened to have my career in his hands,” she said.
Combs allegedly dictated nearly every aspect of her life—from who she could speak to, to how she dressed, and even what nail styles she wore. He told her to call him “Pop Pop,” a name she originally used for her grandfather. It soon became a symbol of the intense power imbalance between them.
Violence, Mood Swings, and Drugs
Ventura said many arguments turned violent. “He would smash me in my head, knock me over, drag me, kick me, stomp me in the head if I was down,” she testified. If she didn’t answer his calls, Combs would blow up her phone or send staff to track her down.
She also testified that Combs provided her with ecstasy and cocaine, which she used to disassociate. Later in the relationship, she became “heavily dependent on opiates.”
Inside the “Freak Offs”
Ventura detailed the “Freak Offs”—multi-day sexual encounters that Combs allegedly arranged with other men and women. The first time he proposed voyeuristic sex, she was “shocked,” but didn’t feel she could say no. By 22, she began participating in Freak Offs to “make him happy,” and said they were often the only time she felt close to him.
The encounters, she said, could last for days. Combs allegedly directed every aspect—from who participated to where it happened and how it looked. Ventura was often responsible for coordinating dancers or escorts, using aliases, and sending photos to Combs for approval. He had strict physical requirements and allegedly told her to confirm the escorts weren’t undercover cops.
She also testified that escorts were flown out for these events in multiple states, and that travel was sometimes arranged by her or a travel agent working with Combs’ team. Prosecutors argue this pattern of cross-state logistics is key to proving the federal sex trafficking charges against him.
Among the more disturbing claims:
- Combs allegedly urinated on Ventura, or demanded others do so.
- One hotel room was so damaged after a Freak Off it had to be redecorated.
- In one incident, Combs filled an inflatable pool with baby oil and made Ventura reapply it throughout the night.
The 2016 Surveillance Footage
Ventura also addressed the now-infamous 2016 altercation at the InterContinental Hotel—the one caught on surveillance video that was shown to jurors multiple times. She said the fight started when she tried to leave a Freak Off early, and Combs allegedly assaulted her. “I felt disgusting. I was humiliated,” she said. “I didn’t have the words at the time to explain how horrible I really felt.”
Day Three: Cassie’s Testimony Continues
Cassie Ventura returned to the stand for her most intense testimony yet. She detailed specific instances of alleged physical and sexual abuse, including the 2011 incident with Kid Cudi, and how Combs reportedly used sex tapes, fear, and violence to trap her in a decade-long cycle of trauma.
The Freak Off Videos
Ventura told jurors that Combs recorded their “Freak Offs” and used the footage as leverage to control her.
- He allegedly replayed videos to intimidate her after fights.
- When she tried to resist participating, he’d threaten to leak them.
- On a flight back from Cannes, after accusing her of stealing drugs, Combs allegedly played videos she thought were deleted—then pressured her into another Freak Off that night.
“He told me he’d embarrass me, ruin my career. I felt like it was the one thing he thought I was good at,” she testified. Text messages shown in court included Ventura begging Combs to delete the files. She said she feared losing everything if the videos ever went public.
Jurors were shown binders of still images from the videos—one female juror clutched her chest; another male juror looked away.
Trauma, Rehab, and a Mental Health Spiral
Ventura broke down in tears as she described attending rehab and trauma therapy in 2023. She said she was suicidal and tried to walk into traffic, but her husband stopped her. “I didn’t want to be alive anymore,” she testified. She said she was addicted to opiates throughout her relationship with Combs, attempted rehab five or six times, and has been sober since 2022.
She testified that she preferred taking ketamine during Freak Offs because it was the most dissociative drug, and she used opiates, IV fluids, and massages to recover afterward. She suffered chronic UTIs, gastrointestinal issues, and once had mouth sores from the combination of drug use and oral sex.
One particularly traumatic memory she testified about is from 2018. Their romantic relationship had already ended, but she agreed to have dinner with Combs for what she thought was a “closure conversation.” She was seeing her now-husband at the time. Combs drove her home, she recalled, “And then he raped me in my living room,” she said on the stand after a long pause. “I just remember crying and saying ‘no,’ but it was very fast,” she testified.
The Threat Against Kid Cudi
In 2011, Combs became enraged when he discovered Ventura was dating Kid Cudi during a Freak Off. He allegedly lunged at her with a wine opener between his fingers after reading some emails that exposed the relationship. She managed to escape the hotel where they were having the Freak Off and called Cudi on a burner phone to pick her up.
Afterwards:
- Combs threatened to release Freak Off videos he had of Ventura as retaliation to humiliate her.
- He allegedly told Ventura he wanted to blow up Cudi’s car.
- At some point, Cudi’s Porsche blew up in his driveway.
After the incident, the three met at Soho House. When Cudi asked what happened to his car, Ventura says Combs coldly replied: “What vehicle?” The relationship ended shortly after. “There was too much danger,” she said in court. “Too much uncertainty if we kept seeing each other.”
The Night That Made a Bodyguard Cry
In 2015, Ventura said Combs assaulted her in a Las Vegas hotel while a party was going on in the next room. “He punched me, kicked me—I was trying to run away and made it into the bathroom,” she told the jury. Combs’ security and management team eventually stepped in to stop the attack. She described how she had “black eyes” and “golf-ball size knots on her forehead. She said that one of Combs’ security guards started to cry when he saw her injuries.
After, she stayed at Combs’ house for nearly a week to recover. One of his sons was there at the same time, and when Combs saw her face over FaceTime, he allegedly told her to put on more makeup so his son wouldn’t see the bruises.
The $20 Million Settlement
Ventura testified that she asked Combs to buy the rights to a memoir she wrote for $30 million. He declined. She filed a civil lawsuit in 2023 and settled within 24 hours for $20 million. This was the first time the settlement amount had been publicly confirmed.
Day Four: The Defense Questions Cassie
Cassie Ventura returned to the stand for her third straight day of testimony—but this time, under cross-examination by Sean Diddy Combs’s defense team, who tried to flip the script. Their strategy? Paint the relationship as complicated, consensual, and far from the sex trafficking allegations at the heart of this federal case.
Texts, Consent, and “Just Words”
The jury was shown years of messages between Ventura and Combs—some sexually explicit, some affectionate, and many centered around the now-infamous “Freak Offs.” In one 2017 message, Ventura wrote, “I love our [Freak Offs] when we both want it.” But in court, she clarified: “Those were just words at that point.”
She testified that although their early relationship involved “open communication,” things quickly shifted. “I needed to feel safe,” she texted in 2009 after one encounter left her feeling “dirty and grimy.” She also told the court that saying yes didn’t always mean she was comfortable—it meant she was trying to avoid conflict, threats, or worse.
Combs’ Drug Dependency
Ventura testified that drug use was constant throughout their relationship. The two frequently took ecstasy, ketamine, and opiates like Norco together—but if she ever used drugs without him, it would trigger explosions of rage. “If we weren’t getting high, or if I wasn’t doing it with him, it was a problem.”
The defense tried to frame Combs’ volatility as drug-related, even walking the jury through an incident where he overdosed on opiates after a Playboy Mansion party in 2012. Ventura said he admitted to taking “a very strong opiate” that night before she took him to the hospital.
Mutual Infidelity and Jealousy
Ventura clarified previously unknown details about her relationship with Kid Cudi. She said the two began dating in 2011 while she and Combs were “on a break,” but that didn’t make things any safer. She got a burner phone to communicate with Cudi, fearing that if Combs found out, he’d retaliate. “I thought it would be way too dangerous to tell him,” she testified.
Combs eventually found out about the relationship during a Freak Off, which Ventura had previously detailed during day three of the trial. She said that she was still having “Freak Offs” with Combs while they were on a break because “it was a job.”
Even after their relationship ended, Combs would bring up Cudi in arguments—often using it as a deflection when Ventura confronted him about other women. “He brought it up quite a bit,” she said.
When the defense pressed Ventura about jealousy, she admitted she had “some jealousy of Ms. Porter,” referring to Kim Porter, the mother of three of Combs’ children. Ventura said it hurt when he’d spend holidays with Porter and their family. She also testified about a woman named “Gina,” who became a recurring source of tension in 2014. When asked if she got angry upon seeing social media posts of Combs with other girlfriends, she said she “was jealous of certain situations,” particularly in 2013 when she wanted to be his main girlfriend.
The defense has tried to paint these arguments as proof of mutual infidelity and a complicated, toxic dynamic—one where both parties were jealous, drug-fueled, and volatile. But Ventura pushed back on the idea that this was just your average messy relationship, and said fear shaped a lot of her decisions, which is why she participated in Freak Offs even when they were on breaks.
Day Five: Cassie’s Testimony Wraps, More Witnesses Take the Stand
After nearly 20 hours on the stand, Cassie Ventura’s testimony officially wrapped on day five of Sean Diddy Combs’ federal criminal trial—and it ended on an emotional note. After she stepped down, two more witnesses took the stand, each delivering new details that prosecutors hope will connect the dots in their RICO case against Combs.
“I Had a Whole Other Job—Basically a Sex Worker”
In one of the most explosive moments, Ventura said that the “Freak Offs” Combs allegedly forced her to participate in weren’t just random sexual encounters—they functioned like a second career. “I had a whole other job,” she said on the stand, clarifying: “Basically a sex worker.” The judge later struck that comment from the record, but the jury heard it regardless.
She also explained how the Freak Offs derailed her music career. Signed to a 10-album deal with Combs’ label, she only released one. “I couldn’t do many of the things I wanted to,” she testified. In the defense’s redirect, they pointed to a 2012 text thread where she turned down a music video appearance with Common because “Puff said no.”
The $20M and $10M Hotel Settlement
In a final redirect, prosecutors asked Ventura if she’d give up the $20 million civil settlement she received from Combs if it meant she never had to endure the Freak Offs. She broke down on the stand.
“I’d give that money back if I never had to have ‘Freak Offs,’” she said through tears. “I would have had agency and autonomy… I wouldn’t have had to work so hard to get it back.”
The defense questioned Ventura about another settlement. She revealed—for the first time—that she reached a separate $10 million settlement with the InterContinental Hotel, where the 2016 assault was caught on tape, just last month.
Homeland Agent Takes the Stand
Yasin Binda, a special agent from Homeland Security’s human trafficking division, was the next witness called by the prosecution. She was the one who handled Combs’ 2024 arrest—and searched his Park Hyatt hotel suite in Manhattan. Binda’s testimony detailed what was found during the search.
Photos from the search were shown to the jury, including:
- Two Ziploc bags filled with baby oil and Astroglide lubricant
- Medication bottle labeled “Frank Black,” Binda said it was identified as clonazepam
- Two bags of pink powder that tested positive for ketamine and MDMA
- $9,000 in cash
Danity Kane’s Dawn Richard Testifies
Then came a face familiar to anyone who watched Making the Band: Dawn Richard, a former member of Danity Kane who worked for Combs from 2004 to 2011. Testifying under oath, she told the jury she saw Ventura “being attacked by Combs” back in 2009. According to Richard, it started over eggs. Cassie was in the kitchen cooking when Combs stormed in screaming about where his food was.
“He proceeded to come over to her and took the skillet with the eggs in it and tried to hit her over the head with it, and she fell to the ground,” she said. Ventura dropped to the ground, partially in anticipation of the hit, and “went into the fetal position,” said Richard.
Combs then dragged Ventura upstairs by her hair, and Richard recalled hearing “glass breaking and yelling.” When asked why she didn’t intervene or call the police, Richard said she was “scared to do anything in fear of what that might mean for me, too.”
The next day, Combs allegedly locked Richard and another woman in a studio, told them what they saw was “passion” between lovers, and warned: “Where he comes from, people go missing if they talk.” Then he handed them flowers.
