After eight months in jail, Sean “Diddy” Combs is having his day in court.

The fallen music, fashion, liquor, and television mogul heard his fate debated before a jury for the first time in a New York City courtroom on Monday, as federal prosecutors and defense attorneys laid out their respective cases about Combs, 55, who is charged with using his wealth and power to engage in sex trafficking, transportation to engage in prostitution, and a racketeering conspiracy.

Combs has been incarcerated in a Brooklyn jail and denied bail since his arrest and indictment in September 2024. The first order of business before U.S. District Judge Arun Subramanian, on the top floor of Lower Manhattan’s regal federal courthouse, was to seat and swear-in a jury of 12 New York residents.

The panel, selected after a week of vetting a jury pool of hundreds, is a multiracial, majority male group who will remain anonymous - eight men and four women - including what appears to be five White men, three Black men, three Black women, and one Hispanic woman. Then came 45-minute opening statements from each side, followed by the first two prosecution witnesses, who immediately delivered salacious details about sexual and violent behaviour from the start. On the first day, the previously fashion forward Diddy donned a distinctly casual look - wearing plain grey slacks and a grey sweater over a white dress shirt.

Entering court, he smiled at the sight of five of his seven children and his mother seated in the second row of the gallery. They waved at each other, and as his twin daughters made hearts with their hands, and he returned the gesture.

My top three takeaways from day one:

Assistant United States Attorney Emily Johnson, one of six women seated at the government’s table, portrayed Combs as a sexual deviant monster - “a cultural icon, a businessman, larger than life, but there was another side to him, that he ran a criminal enterprise." Johnson told the jury, "For 20 years, the defendant, with the help of his trusted inner circle, committed crime after crime." She said Combs coerced and threatened his girlfriends to participate in "freak-offs", typically in luxurious hotel suites – “days-long, drug-fueled, sexual encounters with male escorts against their will.” Anticipating the defence theme, Johnson said, "This case is not about a celebrity's private sexual preferences. The evidence will show the sexual conduct in this case was coercive and criminal." Johnson warned jurors they would hear repeatedly about Combs’ beating and sexually assaulting women he dated, blackmailing them by filming their exploitative sexual encounters, often under the influence of illicit drugs like ecstasy, and paying employees and other people to cover up his offences.

The prosecutor previewed horror stories from three women victims – singer Cassie Ventura Fine, who had a decade-long, on-and-off romantic relationship with Combs, a woman named Jane, who dated Combs for three years, and a personal assistant named Mia.

Defence Attorney Teny Geragos told jurors that all of the sexual activity was consensual and Combs’ partners were "adult, strong, capable women" who chose to continue their relationships and voluntarily participated in his sex parties. "This case is about Sean Combs' private, personal sex life, which has nothing to do with his lawful businesses," Geragos said. Racketeering did not apply, she said. The defence attorney conceded Combs had a bad temper, sometimes got “out of control” with anger and jealousy, and had engaged in assault and domestic violence - he would own that, she said - but those were not the charges on the indictment. "We take full responsibility that there was domestic violence in this case. Domestic violence is not sex trafficking," Geragos said. “They were in a relationship. They were not being trafficked," Geragos said of the women. While Comb’s relationship with Cassie was “a little toxic at times,” Geragos asserted,

"For Cassie, she made a choice every single day for years, a choice to stay with him, a choice to fight for him for 11 years."

Prosecutors didn’t delay showing the jury one of their most powerful pieces of evidence – hotel hallway surveillance camera video from March 2016 showing Combs’ assaulting Cassie on the sixth floor of the Intercontinental Hotel in Los Angeles.

The trial’s first witness, the hotel’s former security director, Israel Florez, described confronting Combs, wearing only a towel and socks, minutes after he threw Cassie to the ground, kicked her twice, and dragged her back to their room.

“Don’t tell anyone,” Combs told him and offered him a “stack of cash,” Florez testified. The witness, now an LAPD officer, said he declined the “bribe.”

Neither Florez nor Cassie called the police.

“I just want to leave,” Florez recalled Cassie saying. Daniel Phillip, the second witness, offered X-rated testimony about his sexual encounters for money with Cassie and Combs. The liaisons began in 2012 when Phillip, a former male strip club manager, was hired for $200 to perform for what he thought was a bachelorette party at Manhattan’s Gramercy Park Hotel.

Instead, Cassie, alone, answered the door wearing red lingerie, high heels, a wig, and dark sunglasses. “We ended up having sex,” Phillip testified, a routine that commenced with rubbing baby oil over each other’s bodies, while Combs was a bystander.

“He was sitting in the corner masturbating,” Phillip said.

The stripper turned escort told the jury left that first night with $4,000. Many more discreet rendezvous followed at other Manhattan hotels and even Combs’ and Cassie’s apartments, featuring Combs-directed-and-recorded sexual encounters with Cassie that lasted from one to 10 hours, that Phillip described in explicit detail.

His highest pay day was $6,000, but Phillip testified he never thought of his actions with these celebrities as prostitution. “I was excited I was in this world.”

On Tuesday, the second day of testimony, the jury will hear from the government’s star witness herself – Cassie Ventura Fine, who is expected to be on the stand for several days.

She is now married to her one-time personal trainer, with whom she has had two children, with their third child on the way. The prosecution will depict her as a victim who suffered beatings and humiliation from Combs, who had signed her to his Bad Boy Records label when she was still in her teens.

She is 17 years younger than him.

“She knew she had no choice,” prosecutor Johnson told the jury about the freak-offs. “Being a willful participant in your own sex life is not sex trafficking,” defence attorney Geragos countered. “Regret does not mean she was coerced.”