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

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It appears that Milo Yiannopoulos, the infamous troll and self-proclaimed dark magician of the digital age, has managed to reinvent himself yet again, this time as a power broker behind the scenes. Having built a career on shock value and controversy, he’s now leveraging his influence in the chaotic worlds of Kanye West and the potential second Trump administration.

Approximately midnight on November 5th, Milo Yiannopoulos received a call from West Palm Beach. According to a source privy to the situation, this call was placed by a member of Donald Trump’s family. This individual was set to appear at Mar-a-Lago shortly, basking in the spotlight alongside the president-elect as Lee Greenwood’s “God Bless the USA” resonated through a room filled with enthusiastic supporters anticipating a victory speech. However, before taking the stage, they reportedly wished to express gratitude personally to Milo for assisting the campaign in tarnishing individuals who were once considered useful but no longer desired in Trump’s circle, as per Yiannopoulos’ account. If this call did indeed occur as described (which, when it comes to Yiannopoulos, is not always certain), it marked a resurgence for the flamboyant far-right provocateur who had gained prominence during the initial Trump campaign but later plummeted due to a string of scandals.

Over the last few months, the notorious 40-year-old has established Tarantula, a talent management firm that intends to utilize the refined talents of a globally recognized troublemaker to guide the careers of several contentious personalities within pop culture. As stated by Yiannopoulos, his initial two clients were the unpredictable New York rapper Azealia Banks and L.A.-based lo-fi indie musician Ariel Pink, who also attended the January 6th event. Other clients have since been added to the roster, including Martin Shkreli, the imprisoned pharmaceutical executive; Los Angeles Apparel, a company owned by American Apparel founder Dov Charney, who has been accused of sexual harassment; and Ye, along with his intermittent partner Bianca Censori. (It should be noted that Yiannopoulos is known for exaggeration, making it challenging to verify the authenticity of his client list. While some of his claimed clients have confirmed working with him, others did not respond to calls from THR.)

Tarantula’s services encompass two main aspects: one is conventional management, involving contract negotiations, strategic planning, and the like; the other is public relations, employing unconventional tactics akin to those used by a daring internet provocateur. As he puts it, “I appear to create smooth paths for individuals who often find themselves entangled in controversies or predicaments that stem from their distinctive communication styles.

Despite being known as a canceled Twitter troll and once leading online harassment campaigns like Gamergate, Yiannopoulos believes his controversial past qualifies him to advise those socially ostracized. Born in the mid-2010s as an editor for Breitbart News and a key figure in the alt-right movement, Yiannopoulos, a flamboyant 30-something British gay man, gained national attention. He significantly influenced the media’s perception of the alt-right through a popular essay titled “An Establishment Conservative’s Guide to the Alt-Right,” published on Breitbart’s website. During Trump’s rise to power, Yiannopoulos also rose, becoming an unexpected symbol of the alt-right. His association with Breitbart’s executive chairman, Steve Bannon, at the beginning of the Trump era helped solidify his brand.

adorned with pearls, Yiannopoulos boldly expressed his contentious opinions about transgender women on Bill Maher’s HBO talk show, where Larry Wilmore bluntly told him to go elsewhere. Yiannopoulos appeared to enjoy saying provocative and offensive things – racist, antisemitic, anti-trans, misogynistic. The demonstrations that accompanied his college campus visits sometimes resulted in violence and arrests, but he seemed to feed off the attention.

Yiannopoulos’ decline from public prominence started when his past remarks advocating for pedophilia came back to light, effectively ending his tenure as an icon of the alt-right movement shortly after it began. (He attributes this fallout to his signature mix of British wit, controversy, and dark humor.) Coincidentally, around the same period, a BuzzFeed article brought to light a video of him singing “America the Beautiful” to a gathering of neo-Nazis in 2016.

In 2017, organizers of the Conservative Political Action Conference abruptly ended his planned keynote speech at their event due to controversial actions. His significant book deal with Simon & Schuster fell apart, prompting a lawsuit against the company. He was banned from Twitter for offensive comments towards Leslie Jones on Saturday Night Live, and Facebook also took action, citing their strict policy against hate speech. His major backers, including Bannon and Robert Mercer of that time, distanced themselves. Additionally, reports emerged suggesting he owed $2 million, primarily to the Mercers. In 2018, he closed down his scholarship, the Yiannopoulos Privilege Grant for “white boys,” a controversial award that had mysteriously lost over a quarter of a million dollars two years prior. (Yiannopoulos has denied any misuse of funds.)

For a period, he openly demonstrated intolerant attitudes, even participating as grand marshal in a 2019 Boston Straight Pride parade – one of the early indications of significant changes ahead. In 2021, amidst his professional turmoil, his four-year marriage to a man known as “John” in media reports dissolved. At this time, Yiannopoulos started undergoing gay conversion therapy. Alongside abstaining from sexual relations, Yiannopoulos also declared his acceptance of Catholicism, renounced drug and alcohol use, which he believes are inherently connected to the lifestyle associated with being gay.

He describes himself as being addicted to sex, feeling like it controlled him rather than the other way around. Now, instead of just being happy, he feels contented, a sensation that’s unfamiliar to him. He sleeps in tranquility these days.

As the new decade unfolded, an individual who had previously identified himself as an “ex-gay” divorcee felt it was time for a change in his professional life. He sought guidance from two outspoken figures at the crossroads of politics and entertainment. These were Ye (formerly Kanye West) and Representative Marjorie Taylor Greene from Georgia. Yiannopoulos found kindred spirits, or perhaps even more polarizing individuals, in these two. He contributed to Ye’s brief second presidential campaign and worked at his fashion and lifestyle brand, Yeezy. In the summer of 2022, he interned for Representative Greene, a role which he humorously referred to as “obviously a joke.

As a gamer, I’d rephrase that statement like this: “I was thrilled when he shared about his journey from being gay to embracing Christianity. It’s an inspiring tale!

However, his time with Greene didn’t last long. Following several turbulent months in Washington D.C., he went back to working for Ye, advancing steadily up the corporate ladder at Yeezy. Throughout this period, there were persistent allegations and lawsuits that trailed him by a few steps.

During his time with Ye (Kanye West), Yiannopoulos’ association occurred during an eventful phase marked by Ye’s release of multiple controversial, antisemitic statements. This actions led to significant consequences such as the termination of Ye’s $1.5 billion deal with Adidas and ultimately his separation from Kim Kardashian. The climax of this period was reportedly a dinner at Mar-a-Lago, which Yiannopoulos claims he arranged, attended by Ye, former President Trump, and the open racist and Holocaust denier, Nick Fuentes.

Milo Yiannopoulos’ second attempt at the presidency failed swiftly; likewise, his collaboration with him came to an end, but not long after, he found himself in a significant position within Yeezy, serving as the chief of staff. A representative from Yeezy stated to The Hollywood Reporter via email that Milo was well-liked and efficient at Yeezy, known for uncovering unnecessary spending and detecting fraud.

Despite his tenure with Yeezy, Yiannopoulos appears to have encountered controversy. An earlier filed lawsuit outlines several suspicious incidents during his leadership, such as reportedly racist actions. For instance, two workspaces for staff were named “Slaves” and “New Slaves,” the latter a reference to a 2013 Kanye West song. Yiannopoulos dismisses these accusations as exaggerated – implying it’s not his place to decide their validity.

 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.” 

As a dedicated admirer, I’d put it this way: “I was disheartened and annoyed when there was an unintentional credit card mix-up, which we now recognize was simply an oversight. Milo promptly repaid the campaign once the mistake was realized. It’s worth noting that Milo and Marjorie continue to keep in contact.

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Yiannopoulos asserts, “I should be included in Tarantula’s list of rebels and instigators. The one person capable of assisting individuals who confront challenges in their relationship with the media, and struggle to reinvent themselves commercially, is someone who has already accomplished this feat.

Tarantula quietly debuted during the summer, as Yiannopoulos mentioned to me in our mid-September conversation. Excluding covert political operations, its first clients were two high-profile individuals: Banks and Pink. Afterward, additional clients joined such as Martin Shkreli (currently imprisoned pharmaceutical executive), Los Angeles Apparel (company led by Dov Charney, former American Apparel founder who has been accused of sexual harassment), and the ongoing divorce saga involving Ye (previously known as Kanye West) and Bianca Censori.

Approximately three weeks following our initial conversation, Yiannopoulos and I found ourselves without a client named Banks. Their spectacular falling out, or at least part of it, was displayed publicly on X platform, where the rapper, who is known for publicly criticizing collaborators online, posted “YOU WERE NEVER HIRED.

Yiannopoulos explained that the artist’s mode of communication could occasionally be through Twitter about you instead of directly messaging you, and it is essential for one to cope with this style.

Later on, Yiannopoulos stated that he had ended things decisively with Banks, referring to her as a previous client of Tarantula Management. However, THR failed to get in touch with Banks for a discussion about their professional relationship with Yiannopoulos; a former lawyer for Banks verified to THR that a management agreement with Tarantula was indeed in place.

Pink, a musician with a long-standing career, who was initially a client of Tarantula’s, lost popularity in the independent music scene after he was spotted attending the Trump rally in Washington D.C. on January 6th, 2021, before the assault on the Capitol later that day.

Pink expressed her belief that Milo is quite skilled in these matters and found our agreement logical, as she shared with THR. Regarding her career, Pink has been entangled in some cancel-culture controversies and isn’t entirely sure how to extricate herself from this predicament. It’s a complex situation for her, one she doesn’t fully understand, but she feels it’s important for her to address it in some way. She’s not an expert on the topic, but her intention is to deal with it somehow.

Over the past fortnight since our last chat, Yiannopoulos claims he’s gained a new client in internet personality Tristan Tate. Together with his brother Andrew, who self-proclaims as the “king of toxic masculinity,” they’ve amassed millions by having women on webcams. However, they are also under allegations for human trafficking in Romania (which they have denied).

Yiannopoulos chose not to reveal Tarantula’s two financial supporters publicly. However, he hinted at their identities: One is connected to the music industry, while the other is an advisor within the Washington Beltway circle, close to President Trump. He stated that the support of these unidentified investors expands his influence into realms he wouldn’t otherwise reach. Currently, Tarantula is involved in selecting candidates for a potential second Trump administration, with a focus on the Departments of Homeland Security and Health and Human Services.

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A look at Milo’s X feed (reinstated following Elon Musk’s takeover) shows he’s sticking to his authentic self – the bold, unrepentant, shocking troll we all encountered a decade ago. He may no longer be making TV appearances or news commentary, but he still wields power behind the scenes. His reported doxxing of Laura Loomer, the conspiracy theorist and Trump ally, is an example – by publishing what was claimed to be her mental health history, he effectively cut her off from the president-elect’s inner circle. Despite Yiannopoulos’s ability to be evasive, he can be effective. This is his signature sales tactic, and if his business flourishes, expect to see similar tactics used more frequently among his clientele, whether they are official or not.

In either Yeh’s disorderly realm or the outskirts of Yiannopoulos’ contribution to the second Trump administration, he intends to continue challenging the norm, chuckling as he performs his mysterious, potentially ominous maneuvers.

Originally, this tale was published in the November 13th edition of The Hollywood Reporter magazine. To stay updated, consider subscribing here.

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2024-11-14 21:27