For many criminal defendants, courtroom reveals boil down to a nice business suit, occasional facial expressions and few words being uttered in public.
For Sean “Diddy” Combs, it’s not that simple.
Fame and fixers had long shrouded some of the darker, more salacious aspects of a life the mogul managed to keep hidden for decades, but his sex trafficking trial dragged all the many faces of Diddy firmly into public view. But as a jury is now deciding his fate on federal charges of sex trafficking, racketeering conspiracy and transportation to engage in prostitution, one thing is clear: Diddy’s blockbuster eight-week trial in Manhattan federal court will have a lasting effect on his public persona even if he is acquitted.
The coast-to-coast power player was portrayed over the past eight weeks as a proud father, chronic cheater, famous rapper, sex freak, domineering boss, caring son, drug addict, domestic abuser, good Christian and boyfriend to many women — all wrapped in a velour tracksuit.
Even testimony from those who knew Diddy best and witnessed his darkest, most extreme sides, depicted a man of many and deep contradictions. Each morning, Diddy walks into the courtroom and hugs his attorneys. He then quickly scans the room, his eyes often lingering on the courtroom pew behind him, where his mother and children sit — his two sons appear regularly, his three 18-year-old daughters turned up for closing statements.
When he spots his mom Janice, who hasn’t missed a day of the trial, he blows her a kiss. “Hi Mommy,” he once mouthed.
Diddy, who built a business empire and allegedly called himself the “king,” seems accustomed to being in control. When evidence is being presented, he slides on his glasses and reads the screen in front of him. He pays close attention, often scribbling on Post-It notes to pass to his lawyers. On one occasion, he faced a harsh reminder that it’s the jury, not him, now in control of his fate; the judge scolded him for “nodding vigorously” and interacting with the jurors.
Any lingering frustration from the reprimand was undetectable weeks later, when Diddy praised the judge for doing an “excellent job.” Addressing Judge Arun Subramanian directly, he stood up from his wooden chair, revealing a burnt orange sweater — one of only five the court permitted him to wear throughout the whole trial. If the man behind the Sean Jean apparel line is bothered by this restriction, he doesn’t show it. He flashed a smile and seemed eager to get the chance to speak.
But Diddy’s not just sitting in court; he’s holding court. Journalists, YouTubers and fans alike pack into the 26th floor of the Southern District of New York courthouse to sneak a glimpse, savoring any surface-level tidbit.
Since the 1990s, the multi-faceted talent has been famous. He won Grammy awards as a rapper, founded a record label, launched an apparel line, ran a TV network, served as the face of Ciroc Vodka, and is a father to seven children. He’s dated celebrities and launched now-celebrities’ careers. He’s rebranded so many times that even his criminal indictment addresses him by numerous names: Diddy, Puff Daddy, PD, Love.
This time in the spotlight, though, his image is in the hands of everyone else: his legal team, prosecutors, reporters, and witnesses. Right off the bat, Teny Geragos, one of Diddy’s defense attorneys, argued that her client is not a criminal, but a “complicated man.”
The word sums up the rapper better than most. Jurors have heard eight weeks of testimony from his ex-girlfriends and former employees, each contributing a piece of the Puff-shaped puzzle. Depending on who was on the stand any given day, Diddy was either charismatic, controlling, belligerent, spiritual, capricious, or sexually adventurous. To many, he was all of the above.
Many witnesses remarked on his charm. People gravitated toward him. Cassie Ventura, his on-and-off girlfriend of 11 years, told the court that she fell in love “very quickly” with Diddy, her then-music producer, after her 21st birthday, when Dallas Austin and Britney Spears showed up to celebrate the young singer. “That was all him,” she recalled. They first kissed that night.
Jane, who dated Diddy from 2021 through 2024 and testified under a pseudonym, was also struck by his magnetism: “I was drawn to him right away.” Their first date lasted five days. “He was larger than life. He had a really big personality. He was very charming,” she recalled fondly, her mouth cracking a smile as she spoke on the stand. Years later, his charisma repaired their relationship. After they had broken up, Diddy texted Jane a sweet message describing how she made a cameo in his dream: “I love you. I miss you. It was great seeing you in my dream last night.” They got back together shortly thereafter.
This allure was also evident in his work life. Several of his former employees testified they were inspired by his energy, talent, and self-made legacy, a man who built himself an empire worth hundreds of millions. As Geragos said: “No one gave him a dollar.” David James, his former assistant, called him “a successful, self-made, brilliant marketer.” George Kaplan, another former assistant, hailed the mogul’s “motivational” energy.
But charm and control went hand in hand. He worked constantly, with some of his former employees recalling they would go days on end without sleep to keep up with him. Ventura, who was signed to Bad Boy Records, testified that Diddy called the shots on her career. He oversaw her record production, her acting career, and even gave the final approval on her clothes and hair. Mia, his former assistant who testified under a pseudonym, recalled that part of her job was to “keep tabs on” Ventura.
Capricorn Clark, another former assistant, also recalled a time when Diddy showed off just how much Ventura obeyed him. "He called Cassie over and he asked her to sit down, stand up, turn around, turn the other way, walk over there, grab that, hand me that, walk back, turn around, go back in the other room," Clark said. Ventura followed his instructions.
The court heard how he directed Ventura and Jane on how to interact with male escorts during “freak offs” — drug-fueled, days-long sex marathons he organized — from ordering when they were to rub baby oil on each other to deciding when it was over. For both women, the sex encounters became so frequent that they came to think of these nights as their job, comparing themselves to sex workers.
These sex marathons would entail days of sex — and using drugs to stay awake — before relying on IV fluids to recover. Hotels where “freak offs” took place were often booked under aliases, like Frank Black, which allowed him to fuel his sexual desires and drug addictions behind closed doors. He later held “movie nights,” during which Jane recalled they would watch porn or their own sex tapes.
Both Ventura and Jane emphasized they were both open to sleeping with an escort initially, but over time grew to dislike “freak offs.” They really only wanted to sleep with Diddy, they each said. He often recorded “freak offs” — and on a few occasions threatened to release the explicit footage of both Ventura and Jane, they testified.
His control over Ventura’s work life meant she felt unable to say “no” to “freak offs,” she told the court; “I worried for my safety, my career. But I also was in love with him so I worried he wouldn’t want to be with me anymore.” Once when she tried to leave a “freak off” early in 2016, Diddy kicked Ventura to the ground before dragging her down the hallway of the InterContinental Hotel — a haunting scene immortalized by security footage.
Diddy offered a security officer $50,000 for the footage of the incident, later handing over a brown paper bag full of cash worth twice that amount. It got leaked to the press eight years later anyway.
The highs were really high and the lows were really low.
The InterContinental incident wasn’t a one-off violent incident. He’s been accused of firebombing Kid Cudi’s Porsche, dangling Ventura’s friend over the 17th floor balcony, and whacking Ventura’s former best friend on the side of the head with a coat hanger, leaving her concussed. When he got in a rage, he even looked different; some recalled his eyes turning black before a physical altercation and one recalled his “devilish stare” after an attack.
But no witness was as familiar with his violence than Ventura. The regular attacks made her feel “worthless, felt like dirt, like I meant nothing, absolutely nothing,” she said, dabbing tears from her cheeks with tissues. Diddy “takes full responsibility for the domestic violence in this case,” Geragos acknowledged in opening statements.
Diddy’s moods were unpredictable. Taking too long in the bathroom or talking to another producer at a party could trigger him to become violent, Ventura recalled. Mia said his mood “changed all the time.” While on the stand, his former assistant Mia still appeared to fear him, speaking softly into the microphone and looking down as she alleged Diddy sexually assaulted her multiple times and once threatened to kill her. She went so far as to say she “believed Puff’s authority was above the police.” Perhaps he believed this, too — during opening statements, the prosecution said: “He called himself ‘the king.’”
Diddy frequented red carpets, traveled via private jet, and had employees catering to his every need, he also dubbed the sex marathons “wild king nights.” During an interview for Diddy’s assistant role, James glanced at a photo of the mogul hanging on a wall in an office and recalled the head of human resources telling him: “This is Mr. Combs’ kingdom. We’re all here to serve in it.”
Witnesses painted a picture of a very particular man. The mogul “wasn’t happy” with the ketchup in London, James recalled. He also “loves applesauce,” including putting it on burgers, Kaplan recalled. These specific particularities also applied to his love life. Diddy preferred women to wear light-colored nails and wear ponytails during “freak offs,” Jane recalled, adding that also suggested she get nipple piercings and veneers. His chief-of-staff helped her set up a piercing appointment; Diddy paid for the veneers. He also had a thing for baby oil. Photos from his houses revealed drawers filled with baby oil, with federal agents seizing hundreds of bottles from his two homes.
In sharp contrast to his vibrant sex life, lies his religious side. Emails shown in court revealed a faithful phrase below Diddy’s email signature: “God is the greatest.” Jane recalled that he had a favorite pastor and would send her sermons. She appreciated that he introduced her to gospel music, she told the court.
These sides to his personality often collided. The rapper posed for red carpet photoshoots right next to Ventura, whose fresh bruises were covered with makeup. He used a TV to enjoy “movie nights” and to watch Dateline, he presumably sent sermons to Jane on the same device he used to film their “freak offs.” Even his inner circle seems conflicted on how to reconcile his many sides.
Ventura, after detailing more than a decade of physical abuse that included rape and leaving her with a “permanent scar” on her eyebrow from when he slammed her head against a bedframe, said that she doesn’t hate him: “I still have love for the past.”
Kaplan recalled walking in on Diddy throwing apples at his girlfriend Gina. He gave his resignation notice one month after the incident, citing his boss’s “physical behavior” as the “central reason” for his departure. Kaplan later went so far as to call his former boss a “God among men.” Asked about his time with Diddy, Kaplan told the court: “It’s a complicated relationship.”
Mia, who alleged Diddy physically harmed and raped her, explained that she sent warm messages to the mogul after she left her employment because she was “brainwashed.” She reflected on her time working for him: “The highs were really high and the lows were really low.”
Jane, who testified about how she felt forced to participate in “freak offs” because Diddy was — and still is — paying her rent, told the court that she still loves him: “I just pray for his continued healing and I pray for peace for him.”
Now, federal prosecutors argue the rapper has yet another side: a criminal finally facing the music. “The evidence is going to show you a very flawed individual, but it will not show you a racketeer, a sex trafficker or somebody transporting for prostitution,” Geragos argued. That’s something only the jury can decide.
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