The Return of Milo Yiannopoulos: Controversial Career, New Ventures

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!” 

But his tenure with Greene was short-lived. After a few chaotic months in D.C., he returned to work for Ye and climbed up the company ladder at Yeezy, with a succession of accusations and legal filings always a few rungs behind.

Yiannopoulos’ stint with Ye notably coincided with a tumultuous period in which the rapper and fashion mogul unleashed several nakedly antisemitic rants — a move that torpedoed Yeezy’s massive $1.5 billion deal with Adidas and helped end the rapper-producer’s marriage to Kim Kardashian. The period culminated with a notorious November 2022 meeting Yiannopoulos claims to have brokered: a dinner at Mar-a-Lago with Ye, Trump and the avowedly racist, Holocaust-denying far-right commentator Nick Fuentes. 

Ye’s second bid for the presidency quickly fizzled out; so did Yiannopoulos’ work with him, but soon enough, he was brought aboard at Yeezy in a top brass role as chief of staff. “Milo was a popular and effective leader at Yeezy with a reputation for finding wasteful spending and discovering fraud,” a Yeezy rep told THR in an email. 

Still, scandal seemed to find Yiannopoulos during his time with Yeezy. A legal complaint filed earlier this year details several questionable moments in his leadership there, including allegedly racist behavior. (For example, two online rooms for staff were labeled “Slaves” and “New Slaves,” the latter for the recently onboarded and also a 2013 Kanye track). Yiannopoulos says the claims were overblown — as if that were up to him to determine. 

 In a separate incident, a so-called whistleblower accused Yiannopoulos of theft and conversion of campaign funds for personal use, pointing to a day in November 2022 — incidentally, the same day as the Mar-a-Lago dinner — when Rep. Greene’s campaign credit card was used to purchase the $7,020 hosting fee Ye’s website, just as a reimbursement of $9,955 was sent to Yiannopolous’ account, as a domain-related payment from Yeezy. Yiannopoulos chalked this up to an error by someone on his personal staff, who he says selected the wrong card from those stored on his web browser. The fiasco led to Ye’s then-campaign treasurer Patrick Krason resigning over a “potentially serious criminal transaction.” Yiannopoulos said as the potential scandal simmered in May 2023 that the accusations from Krason of illegal misappropriation of funds are “ridiculous and easily disproved claims.” 

Isaiah Wartman, a senior adviser to Greene, tells THR, “We were disappointed and irritated by the accidental use of a credit card which we accept was an innocent error. Milo reimbursed the campaign when the error came to light. … Milo and Marjorie remain in touch.”

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“I belong on that list, too,” Yiannopoulos tells me of Tarantula’s collection of firebrands and agitators. “The only person who can really help people who have a countercultural or a provocative or a difficult kind of relationship with the media, and have difficulty reimagining themselves commercially, is somebody who’s done it.” 

Tarantula soft-launched over the summer, Yiannopoulos told me during our initial conversation in mid-September and, clandestine political ops aside, with two well-known live wires as its initial clients: Banks and Pink. A few more clients followed, including imprisoned pharma bro Martin Shkreli; Los Angeles Apparel (the company owned by American Apparel founder and accused sexual harasser Dov Charvey); and the perpetually maybe divorcing Ye and Bianca Censori. 

A few weeks after Yiannopoulos and I first spoke, Tarantula was already down a client, Banks. Their colorful falling out, or at least some of it, played out over X, where the rapper — who has a habit of publicly tearing into collaborators online — posted, “BITCH YOU WERE NEVER HIRED.” 

“You have to be able to weather the way she communicates, which can sometimes be on Twitter about you, rather than in a text to you,” Yiannopoulos would later tell me of the artist.

Yiannopoulos would later claim that he had “hard terminated” Banks, describing her as a former client of Tarantula Management. THR attempted to reach Banks to discuss her working relationship with Yiannopoulos but received no reply; a former lawyer for Banks confirmed to THR that a management contract with Tarantula had indeed been signed.

Tarantula’s other initial client, Pink, a musician whose career stretches back decades, quickly fell out of favor with the indie music scene when he was spotted in Washington, D.C., on Jan. 6, 2021, at the Trump rally that preceded the attack on the Capitol later that day. 

“I do think that Milo has a good knack for this stuff. And our deal makes sense to me,” Pink told THR. “As far as my career goes, I got caught up in some cancel-culture bullshit. And I don’t know exactly what is the process of rehabilitating myself out of that. It’s a really tricky thing for me. I don’t profess to know much about it, but as far as I’m concerned I have to do something about it.”

In the two weeks between our conversations, Yiannopoulos says he found a fresh client in internet personality Tristan Tate, who along with his brother Andrew, the self-anointed “king of toxic masculinity,” has made millions putting women in front of webcams while also facing human trafficking charges in Romania. (They have denied the charges.) 

Yiannopoulos declined to name Tarantula’s two financial backers. But he provided a few clues: One is from the world of music, he says, while the other is a Trump adviser from inside the Beltway. The backing of the two mystery investors, he says, “gives me reach into places I wouldn’t otherwise have it.” Now, he adds, Tarantula is helping place candidates for the in-the-works second Trump administration, with eyes trained on the Departments of Homeland Security and Health and Human Services.

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A glance at Milo’s X feed (his account was reinstated after Elon Musk took over) confirms that he’s remaining true to himself and the vicious, unapologetic, jaw-dropping troll we all met a decade ago. And while he’s no longer appearing on talk shows and cable news — for now — he remains influential behind the scenes. Consider his work allegedly doxxing Laura Loomer, the conspiracy theorist and Trump toadie whom the Trump campaign increasingly saw as a liability. Yiannopoulos published what he purported to be Loomer’s history of mental health issues, and poof went her access to the president-elect’s inner circle. As slippery as Yiannopoulos can be, he can deliver. This is Tarantula’s sales pitch, after all, and if the business takes off, expect to see such tactics multiplied by the number of clients on his roster, official or not. 

Whether in Ye’s chaotic world or the periphery of the second Trump administration he helped — in his small way — usher back in, Yiannopoulos plans to keep disrupting the status quo, cackling along as he works his dark magic. 

A version of this story first appeared in the Nov. 13 issue of The Hollywood Reporter magazine. Click here to subscribe.