Sean Combs trial: Inside Bad Boy empire of threats, violence and bribes

At its height, Sean “Diddy” Combs’ Bad Boy Entertainment was a show business powerhouse, mixing music, video, fashion, liquor and style into a business that made Combs a billionaire.

Combs won praise for his visionary growth and brand management.

But federal prosecutors have another word for Bad Boy: a racketeering enterprise.

The federal trial in New York City includes an allegation that Combs was involved in mob family-style racketeering with coercion, kidnapping, threats and beatings done to cover up a pattern of sexual assaults, sex trafficking and prostitution.

The mogul has publicly and defiantly maintained his innocence even before his arrest last September.

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, prosecutors say.

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 a cadre of company employees, security staff and aides. They allegedly helped organize the freak-offs and then covered up the incidents. Thus far, Combs is the only one facing criminal charges related to the investigation.

Have prosecutors made the case?

What the prosecution has presented

Prosecutors have so far called nearly 30 witnesses to the stand in Manhattan and are expected to finish up with witnesses this week.

They include three women who described graphic sexual assaults, including a woman the defense acknowledged was the key witness, Combs’ onetime lover, Casandra “Cassie” Ventura. It was Ventura’s lawsuit in 2023 that set off the unraveling of the Combs enterprise with its details of sex, violence and freak-offs.

His last former girlfriend, referred to only as Jane in court, described how the freak-offs and coerced sex continued despite the lawsuit and a raid by Homeland Security Investigations until his arrest.

She texted Combs pages of Ventura’s lawsuit immediately after it was filed.

“I’ve been crying for three days and am under stress from reading all of this. I keep having nightmares about forced nights and all the times I felt like I couldn’t say no. I feel like I’m reading my own sexual trauma,” she wrote, according to Legal Affairs and Trials.

On another occasion, she said she texted his chief of staff about the threats he made, writing, “He just threatened me about my sex tapes that he has of me on two phones. He said that he would expose me and send them to my child’s father.”

Jane is one of three women whose testimony is at the center of the trial, the others being Ventura and a former employee testifying under the pseudonym Mia, who also testified she was sexually assaulted.

Was Bad Boy a criminal enterprise?

Under the Racketeer Influenced and Corrupt Organizations Act, known as RICO, there are 35 specific offenses, including kidnapping, murder, bribery and extortion, and federal prosecutors need to show a pattern involving at least two overt acts as part of a criminal enterprise.

Neama Rahmani, a former federal prosecutor, said that to prove RICO, the prosecution must show the existence of not just criminal activity but an actual 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, she said.

They also have to show a pattern of racketeering or two or more RICO predicate acts over a 10-year period.

That’s why the evidence of bribery, kidnapping, obstruction, witness tampering and prostitution is important to the prosecution’s case, she said.

It will be up to jurors to determine if federal prosecutors proved the RICO charge.

R&B singer Ventura, who had a long relationship with Combs, was an early key witness in the prosecution’s case.

Ventura testified she felt “trapped” in a cycle of physical and sexual abuse by him, and that the relationship involved 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 freak-offs.

One of those freak-offs led to an infamous hotel beating, Ventura testified. 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 a movie premiere two days later, where she donned sunglasses and heavy makeup on the red carpet.

A cover-up then ensued, according to prosecutors. Ventura stated that the police visited her apartment. She answered a few of their questions, but told the jury she still wanted to protect Combs at the time.

“I would not say who I was talking about,” she told the jury. “In that moment, I did not want to hurt him in that way. There was too much going on. It was a lot.”

Eddie Garcia, the InterContinental Hotel security guard, testified that Combs gave him a brown paper bag containing $100,000 in cash for the video.

Garcia said after his supervisor agreed to sell the video recording, he met with Combs, Combs’ chief of staff Kristina Khorram and a bodyguard. After Garcia raised concerns about the police, he said Combs called Ventura on FaceTime, handed him the phone and told Ventura to tell Garcia that she also wanted the video “to go away.” After that, Garcia said he took the money and split it with co-workers.

Capricorn Clark, a former assistant to Combs, recalled a 2011 violent incident with Combs.

Clark told jurors Combs forced her from her apartment at gunpoint to go with him to musician Kid Cudi’s home in December 2011. Once there, Combs and Clark entered the empty house, and then Cudi, whose real name is Scott Mescudi, showed up. To avoid getting law enforcement involved, Clark testified, Combs ordered her to call Ventura, who was at that time Combs’ ex-girlfirend, and said they need to convince Cudi not to snitch to the cops. “If you guys don’t convince him of that, I’ll kill all you m—,” Clark quoted Combs saying.

Cudi testified that his Porsche was later firebombed in his driveway with a Molotov cocktail.

Ventura wasn’t Combs’ only alleged sex crime victim. Mia, an assistant testifying under that name, described years of sexual abuse, rape and threats. Combs, she said, first sexually assaulted her at his 40th birthday party in New York in 2009, shortly after she began working for him. In the year that followed, she slept in a bedroom at his home, where she was not allowed to lock the door. Through tears, she testified he raped her. “I was frozen. I didn’t react. I was terrified and confused and ashamed and scared.” Another alleged attack occurred in a bedroom closet where she said Combs grabbed her head and forced her to perform oral sex on him.

Under cross-examination, she said she did not initially tell federal prosecutors that Combs sexually assaulted her and acknowledged sending Combs loving messages in the years after the alleged attacks.

Jane, his most recent ex-girlfriend, described how she endured drug-fueled sex marathons right up until the hip-hop titan’s arrest.

Bryana Bongolan, a friend of Ventura, testified that Combs dangled her over a 17-story balcony and tossed her onto balcony furniture in September 2016.

“I will never forget him holding me on that balcony,” she said as a defense lawyer challenged the date she provided with evidence of Combs being elsewhere at a hotel across the country.