The Milo Yiannopoulos Makeover: The Alt-Right’s Fallen Poster Boy Is Back for Trump 2.0

After years in the wilderness, the newly devout, “ex-gay,” alt-right firebrand is back with a new hustle: running a management firm for scandal-prone celebrities like Yeezy and Marjorie Taylor Greene and working for Trump Land behind the scenes.

By Kevin Dolak

Just before midnight on Nov. 5, Milo Yiannopoulos’ phone rang. On the horn from West Palm Beach, says a source familiar with the matter, was a member of Donald Trump’s family. The caller would soon take the stage at Mar-a-Lago, beaming onstage along with the president-elect as Lee Greenwood’s “God Bless the USA” blasted across a room full of supporters awaiting a victory speech. But first, they wanted to personally thank Milo for helping the campaign smear once “useful idiots,” allies no longer wanted in Trump’s orbit, he says. The call — if indeed it happened as described, which, when Yiannopoulos is concerned, is never a given — capped a return from the ash heap for the once-ubiquitous flamboyant far-right rabble-rouser, who shot to notoriety during the first Trump campaign but fell to earth after a series of bruising scandals.

In the past few months, the 40-year-old enfant terrible has founded Tarantula, a talent management company that would leverage the honed skills of a world-class troll to steer the careers of some of pop culture’s most problematic figures. His first two clients, according to Yiannopoulos, were volatile New York rapper Azealia Banks and L.A.-based lo-fi indie songwriter and Jan. 6 attendee Ariel Pink. More followed, including imprisoned pharma bro Martin Shkreli; Los Angeles Apparel (the company owned by American Apparel founder and accused sexual harasser Dov Charney); and Ye and his on-again off-again paramour Bianca Censori. (Given Yiannopoulos’ well-known propensity for exaggeration, confirming his actual client list is a bit of a chore. While some of his alleged clients acknowledged they were working with him, others did not return THR’s calls.)

The services Tarantula offers are half traditional management — e.g. contracts and negotiations and reinvention strategies — and half public relations, deploying the type of guerilla tactics only a brazen internet mudslinger could dream up. “I seem to be able to clear paths for people who can sometimes get tangled in controversies and in problems that their unique ways of expressing themselves have created,” he says. 

A canceled Twitter troll may seem like an unlikely guru, but Yiannopoulos claims his tumultuous history makes him an ideal counselor for the socially damned. Yiannopoulos — who splits his time between Detroit and L.A. — burst into the national psyche in the mid-2010s as an editor for Breitbart News and a ringleader in the vicious Gamergate online bullying campaign. By 2016, Trump was rising to power, and so was Yiannopoulos, a flamboyant out-gay 30-something Brit who’d become an unlikely avatar of the alt-right. He helped define the movement for much of mainstream media with a widely circulated treatise titled “An Establishment Conservative’s Guide to the Alt-Right.” It was published on Breitbart’s website, the conservative news outlet whose executive chairman, Steve Bannon, took a shine to the young tech editor at the dawn of the Trump years. A brand was born. 

Clad in pearls, Yiannopoulos was soon declaiming his controversial views on transgender women on Bill Maher’s HBO talk show, where he was told to go fuck himself by Larry Wilmore. Yiannopoulos seemed to revel in saying shocking things — racist, antisemitic, anti-trans, misogynistic. The protests surrounding his appearances on college campuses occasionally led to violence and arrests, but he seemed to thrive on the attention.

Yiannopoulos’ slow fade-out from the public eye began when some old comments he’d made normalizing pedophilia resurfaced, ending his career as an alt-right pinup soon after it began. (The “usual blend of British sarcasm, provocation and gallows humor” were to blame, he says.) Around the same time, a BuzzFeed article unearthed a video of him crooning “America the Beautiful” to a group of neo-Nazis in 2016. 

That’s when organizers of the Conservative Political Action Conference hastily canceled his scheduled keynote address at its 2017 event. His sizable Simon & Schuster book deal imploded, too, which led him to sue the company. Twitter deplatformed him for racist trolling directed at Saturday Night Live’s Leslie Jones, and Facebook followed suit, citing its zero-tolerance policy on hate speech. His wealthy supporters — including Bannon and that era’s right-wing godfather, Robert Mercer — distanced themselves. And then came the reports of his being $2 million in debt, mostly to the Mercers. In 2018, he shuttered his scholarship, the Yiannopoulos Privilege Grant for “white boys,” an unabashed troll of an award that had mysteriously lost more than a quarter of a million dollars two years earlier. (Yiannopoulos has denied any theft of the funds.)

He continued his public displays of bigotry for a while, serving as grand marshal in a 2019 Straight Pride parade in Boston. That was among the first signs of the sea change to come. In 2021, amid his career chaos, his four-year marriage to a man referred to as “John” in press reports ended as Yiannopoulos began gay conversion therapy. In addition to swearing off sex, Yiannopoulos said he’s also embraced Catholicism and cut out drugs and alcohol, which he sees as intrinsically linked to the gay lifestyle. 

“I was an addict — I feel like I was a slave to a drug,” he says of his relationship with sex. “I’m not happier, I’m more content, which is new for me. I go to sleep at peace.”

Well into the new decade, the self-proclaimed “ex-gay” divorcé decided it was time for a career pivot. So he ran into two pairs of open arms, belonging to two even louder, brasher voices at the intersection of politics and entertainment. With Ye (fka Kanye West) and Rep. Marjorie Taylor Greene of Georgia, Yiannopoulos found two kindred spirits, or maybe just two people even more polarizing than he was. He worked on the former’s short-lived second presidential bid then at his fashion and lifestyle brand, Yeezy, and in the summer of 2022 interned for the congresswoman. (The intern title was “obviously a joke,” says Yiannopoulos.)

Greene’s statement when hiring him celebrated his gay conversion and his embrace of Christ: “Great story!”