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The Powerful Celebs Who Acted as Diddy’s Human Shield

Photo Illustration by The Daily Beast/Getty

After decades of courting and mixing with the highest echelons of celebrity, influence, and power, Sean “Diddy” Combs is behind bars following his indictment on three charges for sex trafficking, racketeering, and transportation to engage in prostitution.

According to court documents and witness claims, Combs orchestrated a far-reaching sex trafficking enterprise, earning a threatening reputation for blowing up the vehicles of his adversaries, and assaulting his lovers and employees—and more.

But how could he have evaded justice for so long? One very important strategy for Combs, it seems, was to use his relationships with the rich and famous as a shield.

Combs is a hip-hop figurehead who infiltrated the fashion world to the point that he was able to convince industry icons including Anna Wintour, Marc Jacobs, and Tommy Hilfiger to lend their voices to his rap album, Last Train To Paris. The album’s interludes were a triumph for Combs, displaying the reach he’d achieved within that industry.

Some people close to Combs deny ever seeing him participate in the egregious activities of which he’s accused. According to his indictment, these include trafficking people for the purposes of soliciting sex, and forcibly drugging and threatening victims into participating in elaborate sex performances.

Nevertheless, it stands to reason that at some point over the last couple of decades at least one powerful person might have witnessed some of Combs’ alleged wrongdoing.

And though some who’ve worked with Combs have tried to blow the whistle on him for years—not one of the most powerful people Combs hosted at his infamous parties has come forward.

One claim that perhaps sheds additional light on the complicity of Combs’ friends appeared in the latest lawsuit against him from former Diddy artist Dawn Richards, who alleged that Combs assaulted ex-girlfriend Cassie in front of Grammy-winning musicians Usher and Ne-Yo, as well as Interscope Records co-founder Jimmy Iovine—none of whom intervened.

As for the public, Combs’ use of the public images of his famous friends to dispel rumors that he was engaging in criminal behavior seems to have worked—and for a long time, if the claims turn out to be true.

Photos of Combs with figures people are likely to trust, or at the very least express disbelief they’d ever associate with a known-predator, such as Oprah, Wintour, or Justin Bieber—have been media staples for as long as Combs has been famous.

So it may prove useful to revisit some of those photos and relationships, to examine just how many powerful celebrities Combs had at his disposal to create that human shield.

Ashton Kutcher

Ashton Kutcher and Combs’ friendship is an old one. In the mid-2000s, the pair were so close that they took to touting themselves as the new Rat Pack alongside actor Jamie Foxx.

In a 2019 Hot Ones interview, Kutcher told host Sean Evans that “I’ve got a lot I can’t tell,” about his friendship with Combs. He could be forced to speak up soon, as the Daily Mail claimed the star was “expecting a subpoena” about Combs’ wrongdoing.

Anna Wintour

Diddy and Anna Wintour at Fashion’s Night Out at Macy’s Herald Square on Sept. 10, 2010 in New York City.

Wintour has been photographed partying with Diddy several times. Appearing with the rapper—and sending him that coveted Met Gala invitation—contributed significantly to his acceptance into the upper reaches of the fashion world.

Their friendship extended to plenty of Vogue coverage for the rapper, who has enjoyed regular features and photo shoots in the magazine for decades (the most famous of which likely was 1999’s “Puffy Takes Paris”).

Combs would ultimately develop such a complex about his place in the industry that he would allegedly tell his employees, “When you speak to me, you should imagine that you’re talking to Karl Lagerfeld,” as one anonymously told the Daily Beast in June.

Prince Harry

Kanye West with Prince Harry and Diddy at Wembley Arena in north London, July 1, 2007.

Harry’s buddying up with Combs could certainly give one the impression that his power extends worldwide, as the British prince has been photographed hanging with Diddy.

Jennifer Lopez

Jennifer Lopez and Diddy

When she dated Combs between 1999 and 2001, Lopez wasn’t yet a mega-star. She starred in Selena, her first major movie, in 1997. She was arrested with the disgraced mogul following a shooting at a nightclub in Manhattan and was later released with Combs, without charges.

She hasn’t made a peep about the allegations against her ex-boyfriend, though a source claiming to be close to Lopez told the Daily Mail after the Cassie video that Lopez wouldn’t be speaking up about him as it’s “not her story to tell.”

The Kardashians

Kim Kardashian, Diddy, Khloe Kardashian, and Kylie Jenner attend Diddy’s 50th Birthday Bash on Dec. 14, 2019, in Los Angeles, California.

Members of the influential clan have been frequent guests at Diddy’s excursions and parties for years. Several of them were photographed arm-in-arm with him as recently as 2019. Whatever one thinks of the way their fame came to be, their inclusion in Combs’ orbit has an effect.

Oprah

Diddy and Oprah Winfrey attend The Met Gala on May 3, 2010, in New York City.

The renowned host has been buddy-buddy with Combs for years, further creating a shield of powerful people.

Justin Bieber

Diddy and Justin Bieber perform at the BET-SOS Saving Ourselves Help for Haiti Benefit Concert at AmericanAirlines Arena on Feb. 5, 2010, in Miami, Florida.

Combs was a mentor of Bieber’s when he shot to fame at just 15 years old. Though the internet has long circulated rumors that Bieber may have been privy to some inappropriate things while in Diddy’s circle, the pop star hasn’t spoken about his relationship with the former mogul—even amid all the allegations that have emerged over the past year.

Leonardo DiCaprio

Leonardo DiCaprio and Diddy at the Democratic National Convention on July 29, 2004, at the FleetCenter in Boston, Mass.

DiCaprio was filmed dancing at Combs’ 50th birthday party in 2019, and photographed with him several times over the years as a guest at his parties.

Paris Hilton

Paris Hilton and Diddy attend the Diet Pepsi VMA after-party on September 9, 2007 in Las Vegas, Nevada.

Paris Hilton is another powerful person who seemed to give Diddy her stamp of approval by attending his lavish parties over the years. As an abuse survivor and advocate for young people, Hilton has been strangely silent about the accusations against him, even though she’s posted about having an “epic time” hanging out at his house.

Mariah Carey

Diddy and Mariah Carey

Carey and Combs have been photographed together numerous times, as they both emerged to music prominence around the same time in the late 1990s and early 2000s. She’s also been a frequent guest at his parties.

Jay-Z

Diddy and Jay-Z attend Sean Combs 50th Birthday Bash on Dec. 14, 2019, in Los Angeles, California.

Rapper and mogul Jay-Z is yet another powerful person known to have maintained a friendship with Diddy, as both of them emerged on the hip-hop scene around the same time. They even evaded jail time in the same year, 1999. Later, each of them made entrepreneurship, philanthropy, and the fusing of luxury industries with hip-hop major facets of their personal brands.

Jay has regularly participated in charity events and performed on stage with Combs, and there’s no shortage of photographs that show the two men sharing space over the last 30 years—and yet, Jay-Z has never offered any public thoughts on the downfall of his friend.

Rapper 50 Cent, in his taunting of Diddy, has noted that Jay-Z seemed to abandon Combs amid the allegations from his various lawsuits.

The list of names could go on, but as Combs prepares to stand trial for a wide range of crimes, his celebrity friends remain—so far—united in silence.