Inside Diddy And Anna Wintour's Relationship

Sean "Diddy" Combs' sex trafficking and racketeering arrest reportedly had Hollywood scared. With the threat of a "Diddy List" coming out, that's said to be bigger than the Jeffrey Epstein list, some A-listers have reportedly begun to pay off some accusers to keep them from speaking out. Diddy's ties — from celebrity deaths to his former protégés — are now under the microscope.

Even Jay-Z and Beyoncé had to legally remove false accusations about them doing "nasty things" in relation to the music mogul's scandal. Recently, even Vogue's editor-in-chief, Anna Wintour, was labeled as one of Diddy's "human shields" in the past decades. Here's a closer look at their friendship, ahead of the rapper's trial kicking off on the same day as the Met Gala 2025.

Anna Wintour And Diddy Are Longtime Friends And Collaborators

Anna and Diddy have been photographed together many times. The two are longtime friends and collaborators, with the fashion icon's voice featured on the hip-hop artist's album, Last Train to Paris (2010), alongside Dirty Money and R&B singers, Kaleena Harper and Dawn Richard. Anna is heard saying in between songs:

This is Anna Wintour from Vogue magazine. You are now listening to the Last Train to Paris

Other influential names in fashion were included in the album, like the late André Leon Talley, Marc Jacobs, and Isaac Mizrahi. In the YouTube clip above, Diddy is seen hanging out with Anna at the Vogue office ahead of the magazine's "Fashion Night Out" event on September 10, 2009.

The "I'll Be Missing You" hitmaker was hyping up the party, calling it "hot" almost every second of the three-minute video. But like Diddy's "dangerous" freak-off parties, Fashion Night Out eventually came to an end in 2013 and was later called the "messiest night in fashion."

At that time, Buzzfeed reported that the event led to the following chaos:

• "Dangerous" street parties
• "Near-riot" foot traffic in SoHo
• Reckless passing of free booze, likely including underage people
• Huge crowds that could have easily caused stampedes

FNO "felt like cleaning up your house after you had too many people over," said Jack Sacks, who was working at Brooklyn-based indie designer store, Bird. "Are you happy they're gone? Yes. Was it fun to have them over? Sure."

Anna Wintour Is Reportedly "Rebuffing Anyone" Who Asks Her About Diddy

In September, The Daily Beast released a list of "Powerful Celebs Who Acted As Diddy's Human Shield." Anna was included and credited as "[contributing] significantly to [Diddy's] acceptance into the upper reaches of the fashion world." An anonymous source also told the magazine that it got to Diddy's head. He would apparently say something like:

When you speak to me, you should imagine that you're talking to Karl Lagerfeld.

Early in October, an insider explained Anna's "emotionless" look at Paris Fashion Week following Diddy's arrest. "Diddy is the talk of Paris Fashion Week. It's all anyone is talking about," they told RadarOnline.com. "But Anna is having nothing of it: she doesn't want to talk about her connections to him, and is rebuffing anyone who asks her about it."

Other "human shields" mentioned in the Daily Beast's article were Prince Harry, Diddy's ex-girlfriend, Jennifer Lopez; his close pal, Ashton Kutcher, who was seemingly protecting him on Hot Ones; Oprah Winfrey, and the Kardashians.

Recently, more celebrities were named in a new lawsuit against Diddy. A woman accused Diddy of raping her after being invited to a Las Vegas party attended by Mary J. Blige, Lil' Kim, and Nicki Minaj in 2014. There are also reports of an alleged Diddy list containing the following high-profile names:

• Leonardo DiCaprio
• Jay-Z
• Beyoncé
• Ashton Kutcher
• Paris Hilton
• Howard Stern
• Russell Brand
• Mariah Carey
• Jennifer Lopez
• Russell Simmons
• Usher
• Megan Fox

The list hasn't been verified. It went viral on X (formerly Twitter) after Usher, Pink, and Megan got rid of their old Diddy-related posts on social media. Usher said that his account simply got hacked, but people don't seem to be buying it. Amid the speculations, Diddy's family released a statement, saying they "stand united" in support of their father, slamming "false narratives" about him online.

Diddy's Trial Starts On The Day Of Anna Wintour's Co-Chaired Met Gala 2025

Diddy's trial is set to start on the day of Met Gala 2025. The Bad Boy Records founder previously frequented the annual fundraiser, thanks to his close ties with Anna. Coincidentally, the theme for the event, "Superfine: Tailoring Black Style," would have been a good fit for the musician's aesthetic. He must be having major FOMO behind bars, especially after being denied bail.

One of Anna's co-chairs for Met Gala 2025, A$AP Rocky is also facing legal troubles. He recently pleaded not guilty to felony gun charges from an alleged run-in with a former friend in 2021.

Diddy faces federal charges of racketeering, sex trafficking and transportation to engage in prostitution. In the federal indictment, the "Last Night" performer was accused of "[distributing] a variety of controlled substances to victims, in part to keep the victims obedient and compliant," during his freak-off parties, adding that he "kept videos he filmed of victims engaging in sex acts with commercial sex worker."

In 1999, Diddy was filmed bragging about his freak-offs during an interview with Entertainment Tonight. It seemed like he was predicting his arrest back there. "They going to be shutting them down," he said while promoting his album, Forever. "They're going to probably be arresting me, doing all types of crazy things just because we want to have a good time."