The Devil Wears Sean John: Anna Wintour, Diddy, and the Friendship Fashion Wants to Forget

Anna Wintour made Sean Combs a fashion insider. Now, as he faces sex trafficking charges, their friendship is being quietly erased.

written by Melissa McNair

On the same day Anna Wintour hosted the Met Gala under the theme Superfine: Tailoring Black Style, Sean Combs was scheduled to stand trial in federal court for sex trafficking, racketeering, and obstruction. It wasn’t irony. It was inevitability.

For years, Combs was a fixture at the Gala—seated near Wintour, embraced by Vogue, photographed as fashion royalty. He wasn’t a party crasher by then. He was invited. Curated. Given cover. And now, as federal prosecutors prepare to reveal a network of abuse and coercion under his direction, Wintour pretends she never knew him.

There’s been no acknowledgment of their documented closeness. No comment on why a man now under criminal indictment for orchestrating the rape and trafficking of women and men—some underage, some drugged, many silenced—was repeatedly celebrated by one of media’s most powerful gatekeepers. Wintour has opted for silence, trusting that time and tailoring can obscure complicity.

It’s not her first performance of distance. She hesitated with Harvey Weinstein, too—waiting until it was unavoidable to call his behavior “appalling,” framing her concern around his then-wife, Georgina Chapman. But with Combs, the ties are harder to unravel. Wintour didn’t just tolerate his presence. She rehabilitated it.

She stood by him after the first workplace harassment lawsuit. After the breakup with Cassie Ventura. Even after elevator footage surfaced in 2023 showing him assaulting her. He still appeared at that year’s Gala, cloaked in self-designed couture, interviewed on Vogue’s livestream, his public image untouched. Days later, CNN released the video—him grabbing Ventura by the neck, throwing her to the floor, kicking her.

He issued an apology. Vogue did not.

Now that his name is toxic, she has erased it. Scrubbed him from the narrative without reckoning. It’s a familiar choreography: protect the institution first, and wait for the fire to burn out someone else’s house.

But the record remains. Wintour didn’t just give him a seat at the table. She gave him the tablecloth, the menu, the stage directions. When the structure collapsed, she walked away—quietly, elegantly, as if none of it had been hers to begin with.

SECTION TWO: HOW HE GOT IN

Sean Combs didn’t wait for the fashion world to open its doors—he barged in. In the late ’90s, he was infamous for crashing the Met Gala. By 2010, he no longer had to. Anna Wintour was sending invitations.

The Vogue profile “Puffy Takes Paris” marked the turning point. Approved by Wintour, it cast Combs as a hip-hop innovator infiltrating haute couture. That wasn’t coverage—it was coronation. And from then on, Combs wasn’t just in the room. He was part of the brand.

He appeared beside Wintour at events. She voiced a cameo on his 2010 album Last Train to Paris. Her accent introduced him, literally, as the sound of fashion. It wasn’t just proximity. It was transfer of power.

What he lacked in institutional credibility, she provided. And in return, he offered what Vogue increasingly needed: cultural relevance. Their alliance, dressed up as progress, gave Combs legitimacy and Wintour access.

By 2017, he was staging viral moments at the Met Gala. That same year, a former chef accused him of sexual harassment. The case was settled quietly. Wintour said nothing. She seated him at her table.

That’s how the shield worked. Vogue didn’t just lend prestige—it offered protection. Allegations blurred in the flashbulbs. So long as Wintour kept opening the door, no one asked what was happening behind it.

The 2017 Met Gala photograph—Combs sprawled on the stairs while Cassie posed above him—went viral not for its composition, but its context. This wasn’t a BET party. This was Vogue’s temple. That setting sanctified him.

And when the chef’s harassment lawsuit surfaced that same year, Vogue said nothing. Combs stayed visible. The scandal didn’t stick because the image didn’t change. That was the point. He didn’t need to answer accusations if the institutions around him kept offering applause.

Vogue never asked questions. It published his daughters. Promoted his brand. Covered his elegance, not his violence. In doing so, it taught the public to ignore the rumors—and taught his victims they’d be ignored, too.

The shield wasn’t just Wintour. But she held it highest. And now, as more than 100 accusers come forward, that history can’t be edited out. The invitations may have stopped. But the legacy of who extended them—and why—remains.

SECTION THREE: VOGUE’S INTERNAL CALCULATIONS

According to several insiders who spoke to RadarOnline and The Daily Beast, the decision not to issue a formal condemnation of Combs is being driven less by moral uncertainty than by legal and brand risk. Vogue’s leadership has no interest in positioning itself on the wrong side of history — but they also don’t want to position themselves at the center of a story they helped enable. Any statement would immediately provoke follow-up questions: When did Vogue first hear rumors? Did anyone at the magazine raise concerns? Why was Combs still being invited as late as 2023? There are no good answers to those questions. So the strategy has been to avoid them altogether.

This isn’t new behavior. After the Weinstein revelations, Wintour waited nearly a week before speaking. When she did, the statement was brief, and positioned Weinstein’s wife — fashion designer Georgina Chapman — as the primary victim. That move helped Vogue maintain its support for Chapman’s brand while quietly backing away from the scandal itself. It was damage control, not accountability.

The same playbook appears to be unfolding here. Combs was disinvited from the 2024 Met Gala, reportedly under Wintour’s direction. His presence was scrubbed from coverage. Editorial features once planned around his brand or children were quietly killed. No announcement was made. The erasure was treated as obvious, inevitable, and unworthy of explanation.

To Wintour, this likely feels like control. She is avoiding spectacle. She is protecting the institution. But to those watching from outside — especially to victims of Combs who spent years watching him be celebrated — the silence is not just insufficient. It’s enraging.

It also leaves Vogue vulnerable in the long term. Because silence only works if the scandal ends. And the Combs story is still expanding. As of early 2025, the number of civil claims against him has crossed thirty. More than 120 people have reportedly contacted a single law firm with evidence of abuse. The federal charges against him include trafficking, coercion, and the orchestration of blackmail operations using recorded sexual encounters. Prosecutors have indicated that powerful enablers — not just Combs himself — may be named as investigations continue.

This is where Wintour’s position becomes precarious. She is not accused of any criminal behavior. There is no indication she knew what Combs was doing behind closed doors. But she was part of the system that kept him protected. And if that system starts unraveling, her role in it could move from implied to explicit.

The fashion industry has never been built for accountability. Its hierarchy is opaque. Its allegiances are private. But when a figure as central as Combs is exposed — not just as abusive, but as having used fame and associations to cover that abuse — everyone in the photograph becomes part of the frame.

BIBLIOGRAPHY

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