Combs

R&B artist Cassie Ventura’s movie premiere was days away in March 2016 when her then-boyfriend Sean “Diddy” Combs texted her asking what she was doing.

She already felt “trapped” in a cycle of physical and sexual abuse by him, she told a New York federal jury this week, outlining 11 years of alleged beatings, sexual blackmail and a rape.

She claimed Combs threatened to leak videos of her sexual encounters with numerous male sex workers while drug-intoxicated and glistening with baby oil as he watched and orchestrated the events, known as freak-offs.

“If I pleased him with a freak-off, then my premiere would run smoothly,” she said, according to reporting from inside the Manhattan courtroom from the Associated Press.

What happened next could end up being the beginning of the end of Combs’ public life.

Video footage from that March 2016 night shows Combs punching and kicking Ventura as she cowers and tries to protect herself in front of an L.A. hotel elevator bank. He then drags her down the hall by her hooded sweatshirt toward their hotel room. A second angle from another camera captures Combs throwing a vase toward her. She suffered bruising to her eye, a fat lip, and a bruise that prosecutors showed was still visible during the movie premiere two days later. She donned sunglasses and heavy makeup on the red carpet.

Ventura’s testimony is at the center of the federal trial accusing Combs of racketeering conspiracy, sex trafficking, and transportation for prostitution.

Sweeping allegations

The federal indictment alleges that Combs and his associates lured female victims, often under the pretense of a romantic relationship. Combs then allegedly used force, threats of force, coercion and controlled substances to get women to engage in sex acts with male prostitutes while he occasionally watched in gatherings that Combs referred to as “freak-offs.” Combs gave the women ketamine, ecstasy and GHB to “keep them obedient and compliant” during the performances.

The freak-offs, which prosecutors say sometimes lasted for days, were elaborately produced sex performances that Combs arranged, directed, masturbated during, and often recorded, according to the indictment. Prosecutors allege in a detention memo filed in court that the freak-offs occurred regularly from at least 2009 through 2023 and that the hotel rooms where they were staged often sustained significant damage.

Combs’ alleged “criminal enterprise” threatened and abused women and utilized members of his enterprise to engage in sex trafficking, forced labor, interstate transportation for purposes of prostitution, coercion and enticement to engage in prostitution, narcotics offenses, kidnapping, arson, bribery and obstruction of justice, prosecutors said. In bringing so-called RICO charges, prosecutors in opening statements said Combs was helped by cadre of company employees, security staff and aides. They allegedly helped organize the crime and “freak-offs” and then covered up the incidents. Thus far, Combs is the only one facing criminal charges related to the investigation.

Combs’ attorney this week said her client was far from perfect but that the charges were overblown.

“Sean Combs is a complicated man. But this is not a complicated case. This case is about love, jealousy, infidelity and money,” Combs’ lawyer Teny Geragos told jurors. “There has been a tremendous amount of noise around this case over the past year. It is time to cancel that noise.”

How Ventura and Combs met

Jurors heard that Ventura was 19 when she met the 37-year-old Combs in 2005, and she signed a 10-year contract with his Bad Boy Records label. About two years later, he had Britney Spears come to her 21st birthday party, where Ventura and Combs kissed and their relationship began, she said. She testified that the freak-offs became a way of life, and she even stepped away from her own birthday party for one.

Cassie Ventura, left, and Sean “Diddy” Combs arrive at the Los Angeles premiere of “Can’t Stop, Won’t Stop: A Bad Boy Story” at the Writers Guild Theater on June 21, 2017, in Beverly Hills.

(Chris Pizzello / Invision / AP)

Combs, she told jurors, required her to let a male sex worker urinate in her mouth. That man and others were paid thousands of dollars to have sex repeatedly for 36 to 48 hours, she told the jury.

On the stand, Ventura identified 13 male sex workers through photos presented by prosecutors that she said Combs’ had her recruit for the freak-offs. Hers and Combs’ relationship would end on a day in 2018 when she met him for dinner and he raped her on her living room floor, she testified.

Violence

During four days of testimony, Ventura, who is eight and a half months pregnant, described being raped, beaten at least six times, most severely in 2009.

In the 2009 attack, she testified that Combs was “stomping” on her face after he discovered she was dating rapper Kid Cudi. Kid Cudi, whose real name is Scott Mescudi, had his car torched a short time afterward. Prosecutors allege in court papers that Combs ordered it.

Legal analysis

Legal experts say the testimony is designed to build the federal case against Combs, even if on the surface it does not appear directly related to the charges he’s facing.

“Why is the government talking about rape and assault when the charges are RICO and sex trafficking?” said former federal prosecutor Neama Rahmani. Well, he said, “what separates sex trafficking from consensual sex between adults — which the defense is arguing — is force, fraud or coercion.”

“Ventura’s testimony that she was given drugs to the point of throwing up … and forced to have sex when she was menstruating or had a UTI is evidence of coercion,” he said.

Rahmani said that Ventura’s portrayal of Combs as a gun-brandishing mogul who beat her on multiple occasions, tracked her movements and sent a security team to find her is evidence of force.

Then there were the alleged threats. She recounted that during a commercial flight in 2013, Combs pulled out his laptop and began playing a freak-off recording as they sat together. She said Combs told her that he was going to embarrass her and release them.

“I feared for my career. I feared for my family. It’s just embarrassing. It’s horrible and disgusting. No one should do that to anyone,” Ventura said.

Authorities raid Sean “Diddy” Combs’ Los Angeles home as part of an ongoing sex trafficking investigation

(Eric Thayer / Associated Press)

Rahmani said the racketeering charge against Combs requires prosecutors to prove the existence of a criminal enterprise.

“People typically think of the mob, street gangs, or drug cartels, but any loose association of two or more people is enough like Combs’ entourage,” the former federal prosecutor said. They must show two or more predicate acts over 10 years.

“That is why the evidence of bribery, kidnapping, obstruction, witness tampering and prostitution is important,” he said.

LAPD officer testimony

Israel Florez, a hotel security guard who confronted Combs in 2016, now a Los Angeles Police officer, testified Combs flashed a bundle of cash at him — something he believed was an attempted bribe. He rejected it, he said.

Combs’ defense is seeking to paint Ventura as participating in the behavior, recruiting and paying sex partners, acquiring narcotics and texting to push for freak-offs that were part of a swingers’ lifestyle. She is one of four alleged victims in the case, with jurors expected to hear from at least three of them.

On Thursday, defense attorney Anne Estevao had Ventura read a series of loving texts to Combs and got Ventura to testify she’d watched Combs have sex with another woman on multiple occasions. To support the swingers’ defense, the lawyer produced a 2009 text where the singer declared, “I’m always ready to freak off.”

Ventura sued Combs in the fall of 2023, accusing him of years of physical and sexual abuse, triggering a cascade of lawsuits and allegations by others who say they’re victims of Combs and eventually, a raid by Homeland Security on his L.A. and Miami homes and his arrest. Ventura acknowledged Wednesday that she got a $20-million settlement within days of filing her lawsuit.

Combs attorney pushes back

During opening statements in a Manhattan federal courtroom, Geragos, one of Combs’ defense attorneys, drew a distinction for jurors between the violence they would hear testimony about and the charges Combs was facing, saying “domestic violence is not sex trafficking.”

She said the video of Ventura’s assault in the hotel was indefensible, but that the singer “made a choice” to stay with Combs for 11 years.

After the attack, a friend called police to Ventura’s home, she testified. But when officers arrived, she did not identify Combs as the culprit.

The prosecutor asked her why she did not talk. “In that moment, I didn’t want to hurt him that way. I wasn’t ready,” she replied.

On Thursday, the defense cross-examining Ventura sought to change the narrative using dozens of text messages between Combs and Ventura. In a July 2013 text message exchange, Comb’s defense lawyer noted that Cassie raised the idea of having a “freak-off,” writing to Combs: “Wish we could’ve FO’d before you left.”

Using the text message exchanges, the defense lawyer highlighted Ventura’s admitted jealousy over the attention he gave other women.

“You’re making me look like a side piece and that is not what I thought I was,” Cassie told Combs in a 2013 text message.

Estevao tried to recast the hotel incident as the result of the two taking a “bad batch” of the psychedelic stimulant MDMA during a “freak-off” before the hotel beating.

During her testimony this week, Ventura testified that Combs allegedly overdosed on opioids while partying at the Playboy Mansion in 2012. While she wasn’t there, she said, he told her about it.

Ventura’s testimony ended on Friday.

The Associated Press contributed court testimony for this analysis.

Amid all of Casandra Ventura’s troubling testimony this week about life with Sean “Diddy” Combs and his “freak-off” fetish, don’t be troubled thinking about what might have happened between Combs and Justin Bieber, who was launched into the mogul’s circle when he was a teen.

Despite persistent speculation as footage of the two together has surfaced, Team Bieber said Thursday that nothing happened. Move along, nothing to see here.

The speculation comes at a time when Bieber has been worrying fans with photos showing him smoking — a shot posted Thursday had the self-declared former substance abuser sitting with a bong quite obviously in his lap — and “It’s a cult” rumors about the church he has been attending, Churchome in Beverly Hills. (Churchome pastor Judah Smith denies those rumors, by the way.) Bieber’s decision in recent years to sell his catalog for $200 million is said to have been motivated by the pop star allegedly finding himself completely broke despite generating many millions for himself and others while touring.

The new dad’s marriage is rumored to be in trouble as well, though on Friday the Biebs tagged wife Hailey in an Instagram story showing a male lion lovingly caressing a female lion with its nose and teeth.

Combs, of course, is on trial on charges of sex trafficking, racketeering and more. This week in court has seen dramatic testimony from Combs’ former girlfriend Cassie.

But back to Bieber, who was discovered by Scooter Braun in 2008 and quickly signed to a label run by Braun and Usher. Usher was a Combs protégé who was sent by record executive and producer L.A. Reid to live with the mogul in the ’90s and maybe learn a few things. The “Yeah” singer was 15 when he moved to New York. Combs became Usher’s legal guardian.

Reid wrote in his 2016 tell-all memoir “Sing to Me,” via Rolling Stone, “‘Will you take this kid and teach him your swagger?’ I said. ‘Can you just give him some of your flavor?’ And so I sent Usher to New York for what I called the ‘Puffy Flavor Camp.’”

He added, “I was turning him over to the wildest party guy in the country at an age when I still needed to get his mother’s permission, but he went to New York for almost a year. I didn’t know whether I was being irresponsible or having an epiphany.”

Usher would tell Howard Stern in 2016 that he “got a chance to see some things” while living with Combs.

“I went there to see the lifestyle, and I saw it. I don’t know if I could indulge and understand what I was even looking at,” he said on Stern’s show. “I had curiosity of my own. I just didn’t understand it. It was pretty wild. It was crazy.”

Usher said he was mostly focused on making music at the time, no matter what “curious” things might have gone on around him.

So when Bieber and Usher connected, could a Combs meet be far behind?

Sean “Diddy” Combs, from left, Justin Bieber and Rick Ross at a Ciroc vodka party in Atlanta in early 2014, when Bieber was 19.

(Prince Williams / FilmMagic via Getty Images)

Combs and the “Baby” singer made news with an interview on Jimmy Kimmel’s show after the “Justin Bieber’s 48 Hrs with Diddy” video was posted on YouTube in November 2009.

In the video, Combs showed Bieber a silver Lamborghini and told him, “The keys is yours, you know, when you hit 16.” That was after Bieber pitched driving it right away with Combs in the passenger seat, because he had his permit. After staring at the kid for a moment, Combs simply said, “No.” Then he promised him the mansion when he turned 18. Combs didn’t have legal guardianship of Bieber like he did with Usher, he said, but they would be together for the next 48 hours.

“He knows better than to talk about the things that he’s done with big brother Puff on national television,” Combs said later in the Kimmel interview, adding, “Everything ain’t for everybody.” That was after he described Bieber as “a little brother” and “one of the greatest kids you could ever know” who could always call up and ask him for industry advice.

The two would continue to cross paths, including at parties for Combs’ vodka Ciroc, a brand the embattled mogul cut ties with in January 2024.

Bieber’s camp released a statement Thursday asserting that nothing untoward ever happened between the two.

“Although Justin is not among Sean Combs’ victims, there are individuals who were genuinely harmed by him,” a spokesperson for Bieber told TMZ. “Shifting focus away from this reality detracts from the justice these victims rightfully deserve.”

The Times was unable to reach a Bieber representative Friday.

NEW YORK — R&B singer Cassie was forced under cross-examination Thursday to read aloud explicit messages with her former boyfriend Sean “Diddy” Combs, some of which expressed enthusiasm for sex with other men at Combs’ behest that she previously testified she “hated doing.”

Lawyers for Combs are seeking to show the jury that Cassie was a willing participant in his sexual lifestyle and say that, while he could be violent, nothing he did amounted to a criminal enterprise. Combs has pleaded not guilty to federal sex trafficking and racketeering charges.

Prosecutors say he exploited his status as a powerful music executive to violently force Cassie and other women to take part in these drug-fueled encounters with sex workers, called “freak-offs,” which sometimes lasted days. He’s also accused of using his entourage and employees to facilitate illegal activities, including prostitution-related transportation and coercion, which is a key element of the federal charges.

Messages between Combs and Cassie — both romantic and lurid — were the focus of the fourth day of testimony in a Manhattan courtroom. Defense attorney Anna Estevao read what Combs wrote, while Cassie recited her own messages.

Cassie, whose legal name is Casandra Ventura, read messages to Combs containing graphic details about what she wanted to do during the freak-offs. At one point, she asked for a short break from the readings, which Judge Arun Subramanian granted.

In August 2009, Combs asked when she wanted the next encounter to be, and she replied “I’m always ready to freak off.” Two days later, Cassie sent an explicit message and he replied in eager anticipation. She responded: “Me Too, I just want it to be uncontrollable.” Combs’ lawyers have insisted that all the sex at the freak-offs was consensual.

Later that year, however, she also sent Combs messages that she was frustrated with the state of their relationship and needed something more from him than sex.

While reading their more affectionate conversations, Cassie testified that Combs was charismatic, a larger-than-life personality.

“I had fallen in love with him and cared about him very much,” Cassie said. Estevao spoke gently during the cross-examination, which had such a friendly tone at times that the lawyer and witness seemed like two friends chatting.

Cassie, however, did complain once that jurors weren’t hearing the full context of the messages the defense was highlighting, saying, “There’s a lot we skipped over.”

A packed courtroom watches Cassie’s testimony

As the messages were read, Combs appeared relaxed at the defense table, sitting back with his hands folded and his legs crossed. The courtroom was packed with family and friends of Combs, journalists, and a row of spectator seats occupied by Cassie’s supporters including her husband.

The 38-year-old Cassie — who is in the third trimester of pregnancy with her third child — has been composed on the witness stand. She cried several times during the previous two days of questions by the prosecution, but for the most part has remained matter-of-fact as she spoke about the most sensitive subjects.

The Associated Press does not typically name people who say they have been sexually abused unless they come forward publicly, as Cassie has.

During a break, Combs stood at the defense table, huddling with his lawyers, holding a pack of Post-It notes in one hand and a pen in the other. At one point, he turned to the gallery and acknowledged a few reporters who were studying his demeanor. “How you doing?” he asked.

Combs’ daughters were not in the courtroom Thursday as the explicit messages were read and shown to the jury.

Jurors leaned forward in their seats to follow along as the messages were displayed on monitors in front of them in the jury box. One woman shook her head as a particularly explicit message was shown. A man stared intently at the screen, pressing his thumb to his chin. Other jurors appeared curious and quizzical, some looking at Cassie or jotting notes.

Cassie rejects ‘swingers’ label

Cassie’s testimony on cross-examination was in contrast to Wednesday, when she described the violence and shame that accompanied her “hundreds” of encounters with male sex workers during her relationship with Combs, which lasted from 2007 to 2018.

While prosecutors have focused on Combs’ desire to see Cassie having sex with other men, she testified that she sometimes watched Combs have sex with other women. She said Combs described it as part of a “swingers lifestyle.”

Estevao asked Cassie directly whether she thought freak-offs were related to that lifestyle.

“In a sexual way,” Cassie responded, before adding: “They’re very different.”

Cassie said Tuesday that Combs was obsessed with a form of voyeurism where “he was controlling the whole situation.” The freak-offs took place in private, often in dark hotel rooms, unlike Combs’ very public parties that attracted A-list celebrities.

She testified she sometimes took IV fluids to recover from the encounters, and eventually developed an opioid addiction because it made her “feel numb” afterward.

When questioned by Estevao, Cassie agreed that Combs once communicated to drug dealers in Los Angeles to stop delivering drugs to her, and he suggested she get treatment. Cassie said Combs wanted her to do drugs with him only, not friends.

Cassie’s lawsuit sparked case against Combs

Cassie testified Wednesday that Combs raped her when she broke up with him in 2018, and had locked in a life of abuse by threatening to release videos of her during the freak-offs.

She sued Combs in 2023, accusing him of years of physical and sexual abuse. Within hours, the suit was settled for $20 million — a figure Cassie disclosed for the first time Wednesday — but dozens of similar legal claims followed from other women. It also touched off a law enforcement investigation into Combs that has culminated in this trial.

Combs, 55, has been jailed since September. He faces at least 15 years in prison if convicted.

Sisak and Neumeister write for the Associated Press. The AP’s Julie Walker in New York and Dave Collins in Hartford, Conn., contributed to this report.

May 15 (UPI) — Former longtime girlfriend Cassie Ventura faced cross-examination from Sean “Diddy” Combs’ attorneys during court proceedings on Thursday.

Defense attorneys asked Ventura if she heard “after the fact” about an alleged incident in which Combs, 55, is accused of throwing one of Ventura’s friends into patio furniture while on a balcony.

Ventura said she witnessed it and did not hear about it later.

Combs’ attorneys also asked how taking too much ketamine affected her.

She said it caused her to “disassociate” and made her feel like “you’re not there.”

‘Get-high’ partners

Ventura confirmed she and Combs referred to each other as “get-high partners” and that she was addicted to opiates that a friend supplied to her while she was Combs’ girlfriend.

She said Combs was unhappy about her opiate addiction and called it hypocritical of him.

Ventura also confirmed she tried cocaine and many other drugs with a friend.

Combs told her to stop doing drugs with her friends, but her drug use only was a problem when she wasn’t doing them with Combs.

She said he only wanted her to do drugs with him and would get “explosive” if she did drugs when he did not know about it.

Combs’ attorneys also asked if Combs in 2016 told Los Angeles drug dealers to stop selling drugs to Ventura while he was trying to get her to stop using drugs.

She said he made the request at some time but did not know during which year.

Injured friend’s payout

An attorney also asked if Ventura witnessed Combs allegedly throwing a wooden clothes hanger at one of her friends.

She said she was in the bathroom at the time, heard the commotion and saw her friend was injured when she emerged from the bathroom.

The incident occurred while she was dating the man with whom she now is married, but Combs was unaware of the relationship at the time, Ventura testified.

The friend who was injured later demanded payment for the incident, which Ventura said she paid because she felt responsible.

Documented expressions of love

Combs’ attorneys also showed text messages and emails in which Combs and Ventura expressed their love for one another and she wanted him to give her more attention.

The defense attorneys have accused Ventura of trying to get revenge on Combs and said she wants money.

They say the sex acts were consensual acts among adults.

Ventura was Combs’ girlfriend for about 11 years and during the first two days of his trial testified about ongoing physical abuse and medical problems she experienced due to what she called forced participation in sex “freak offs” that she says Combs organized.

She said Combs, 55, recorded the sex acts on video, used the tapes to blackmail her and others, and provided drugs during orgies and atother times.

Combs is charged with one count of racketeering conspiracy; two counts of transportation to engage in prostitution; and two counts of sex trafficking by force, fraud or coercion.

He has pleaded not guilty to the five felony charges that could put him in prison for life if he is found guilty on all of them.

The trial is being held in the U.S. District Court for Southern New York in the Manhattan federal courthouse in New York City.