Trigger Warning: This article mentions graphic details about sexual abuse and violence.
At this point in politics, whenever someone talks about Donald Trump, we remember his indirect jabs and all the controversies he’s been a part of, which the media cannot stop discussing. While scandals and Trump often seem to be sides of the same coin, many believed that the 78-year-old may not have any connection whatsoever in Sean “Diddy” Combs’ recent s-x trafficking and racketeering trial. Still, an old video clip suggests the two shared a jovial history.
A resurfaced moment from Trump’s reality show The Celebrity Apprentice is tempting fresh attention — and commentary online, with one user on X (formerly Twitter) saying what many are thinking: “There is always a video, isn’t there?”
According to The List, Diddy formed the girl group Danity Kane in 2005 on MTV’s Making the Band. Years later, group member Aubrey O’Day appeared on Season 5 of Trump’s Celebrity Apprentice.
During a scene from the show, O’Day mentions her former boss, saying, “Working for Diddy for six years trained me to be perfect.” Donald Trump quickly cut in, “Working for Diddy?” and followed with, “I love Diddy. He’s a good friend of mine; he’s a good guy.”
Later, after calling Diddy a “good guy,” Donald Trump immediately asked Aubrey O’Day, “Is he a good guy?” — a loaded question. O’Day hesitated before replying, “I don’t want to answer that question…” Still, Trump stood firm: “Well, I think he’s a good guy. I’m gonna stick up for him.”
This interaction now appears to have been Trump hinting at knowing more about Diddy’s conduct than he let on, even as he defended him publicly. Given the larger context of Trump’s controversial associations, including his connection to Jeffrey Epstein and the infamous Access Hollywood tape, the video feels less surprising than it might have a decade ago.
Sean “Diddy” Combs has been convicted on charges ranging from trafficking and racketeering conspiracy to claims of engaging in prostitution. Following his arrest on September 16, 2024, in New York, the disgraced rapper was at Brooklyn’s Metropolitan Detention Center. The case has seen several new developments since then.
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As per BBC, Diddy allegedly physically assaulted his then-girlfriend, singer Casandra Cassie Ventura, who testified against the music mogul in court in May. With a decade-long relationship with Combs, the singer was eight months pregnant and expecting her third child with husband Alex Fine as she spoke in front of the jury.
She described meeting Combs at 19, when he signed her to his label, soon beginning a relationship marked by control, violence, and emotional manipulation. She said he used his financial power over her and became physically abusive. Jurors were shown graphic evidence, including images and videos, most notably surveillance footage from a 2016 Los Angeles hotel, where Combs was seen beating and dragging her.
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Reportedly, Eddy Garcia, who worked in the hotel where the incident occurred, testified that Diddy signed a non-disclosure agreement (NDA) confirming that the USB drive held the only video copy. Once the deal was sealed, he says Diddy handed him a brown paper bag filled with $100,000 in cash.
The viral video was a result of a “freak-off,” a term for s-x acts involving paid male escorts while Combs watched and filmed. Cassie said that to please Diddy, the whole scene turned into repeated humiliation and abuse. Lawyers in Diddy’s defence, however, have acknowledged that Combs was abusive but argue that this case is about domestic violence, not criminal conspiracy or trafficking.
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They presented messages from Cassie Ventura, seeming to show an eagerness for the encounters and highlighting mutual drug abuse, adultery, and jealousy, aiming to depict the relationship as messy but consensual. Ventura maintained that the texts didn’t reflect her feelings, saying she was emotionally trapped.
Besides Cassie, The Mint reported that another former partner of Diddy, who testified under the pseudonym Jane, revealed that the music mogul twice refused her requests for male entertainers to use condoms during sexual encounters. She claimed that Diddy fooled her and dismissed her request to use protection, which made her feel guilty when she asked for it.
Jane, who dated Combs from 2021 to 2024, shared that the relationship quickly turned into one centred around frequent, long-lasting sexual encounters with male escorts in hotels. He threatened them when she asked him to stop paying her rent.
Jane presented several proofs, including footage and pictures, against Diddy before she said, These encounters, she said, could have lasted more than 24 hours.
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In one instance, she recalled breaking down after Combs abruptly left following a group encounter despite having promised her a private evening together. “I hung onto those words—’just’ just a little bit’,” she said. “I felt awful knowing he was going to leave me alone.” (via The Mint).
As Diddy’s case reveals a new angle with every fresh detail, the 55-year-old public figure has pleaded not guilty to five federal charges, including s-x trafficking and racketeering conspiracy. While the case is ongoing, it has truly exposed the dark side of glamour and Hollywood to the world.
