Old Photos of Diddy With Harvey Weinstein Has Everyone Saying the Exact Same Thing

Trigger Warning: This article contains themes of sexual violence that some readers may find distressing.

Amid mounting legal troubles, photos have resurfaced showing Sean "P Diddy" Combs socializing with disgraced movie mogul Harvey Weinstein at high-profile fashion events. The images, which have sparked renewed interest on social media, capture the two once-powerful figures in seemingly friendly exchanges during New York's elite fashion circuit. Everyone, as such, cannot stop talking about the astonishing similarities between the cases of the entertainment industry tycoons.

In one telling snapshot, the Bad Boy Records founder can be seen shaking hands with Weinstein at the Sean John Fall 2008 show during the Mercedes-Benz Fashion Week. Another photo from the 2008 CFDA Fashion Awards shows the pair posing together—Diddy sporting a crisp white suit with a black tie while Weinstein stands beside him in traditional black attire. These images have taken on new significance as both men face(d) serious legal challenges.

Diddy is still awaiting his federal trial, which is scheduled for May 5, 2025, at the Metropolitan Detention Center in Brooklyn. The rap mogul faces grave charges, including sex trafficking, racketeering conspiracy, and transportation to engage in prostitution, as per the BBC. Diddy's legal team has responded to the allegations. His attorney, Erica Wolff, stated: "We cannot address every meritless allegation in what has become a reckless media circus. That said, Mr. Combs emphatically and categorically denies as false and defamatory any claim that he sexually abused anyone, including minors."

The controversy surrounding both men has put non-disclosure agreements (NDAs) back in the spotlight. Legal experts have noted that Diddy's NDAs were reportedly among the 'broadest non-disclosure agreements' they had encountered, though such extensive silencing mechanisms are not uncommon among powerful figures in entertainment, as per Deadline.

Weinstein is currently incarcerated at New York's Rikers Island after a Los Angeles jury convicted him of rape and sexual assault; he maintains that everything that transpired was consensual and that he is innocent, as per AP News. Still, although Weinstein had nothing to do with Diddy, there are some disturbing parallels between both cases regarding power in the entertainment industry.

A case in point: former TV host Rosie O'Donnell, who used to live near Diddy on Miami's fancy Star Island, recently made some comparisons between the two. "Do you just get to be so big — like Harvey Weinstein did — that he thought, 'Well I control Hollywood, I control the Oscars, I can sleep with any actress I want, whether they want to or not,'" O'Donnell pondered in a recent TikTok video. 

In her candid TikTok commentary titled "todays news," O'Donnell also revealed her own brief interaction with Diddy, recounting how she had once been turned away from his New Year's Eve party by security. She described Diddy's actions the following day as 'unbelievably over the top and extraordinary.' As an act of apology, he reserved an entire movie theater for her family, allowing them to enjoy movies all day. Expressing her shock at the recent allegations, O'Donnell remarked, "Sex trafficking? That's serious, man," as per New York Daily News.

Follow @rosie for more pop culture-related content.

If you are being subjected to sexual assault, or know of anyone who is, please call the National Sexual Assault Hotline at 800.656.HOPE (4673)