An Evening With Milo Yiannopoulos

The conservative firebrand dishes on culture, politics and his new book, 'Dangerous.'

August 10, 2017 5:00 am

I walked into an Italian restaurant on the Upper East Side recently. The maître d’, eager to have a customer, wanted to seat me immediately. “Is there a reservation for Milo?” I asked cautiously.

No reservation, but I could take a seat anywhere I like, the maître d’ said. I texted Milo Yiannopoulos’ publicist to check if I was at the right restaurant. The nearly empty restaurant reminded me of the dinner assassination scene with Michael Corleone in the first Godfather movie. A self-described “free speech fundamentalist” and former Breitbart News writer, Yiannopoulos loathes most journalists. But would he really put a hit on me before we could discuss his new book, Dangerous?

A text popped up on my phone: “Hi Tom. Milo here. Just pulling up. Are you inside the restaurant?” I jumped out of my seat to meet him at the curb. A black SUV with tinted windows was waiting for me. Yiannopoulos, wearing a black military-style jacket, white shirt, gold chains and aviator sunglasses, opened the door to greet me. He is tall and thin with blonde highlights streaked through his dark hair.

We quickly grabbed a table because the publicist said we only have 30 minutes. (We ended up talking for nearly two hours.) To begin, we ordered a bottle of sparkling water and he asked for a black coffee. Yiannopoulos quit drinking after a video surfaced of him making glib comments about pedophilia and prompted him to retreat from public life briefly. He nursed his coffee and water as we chatted. The wait staff by the kitchen rubbernecked and wondered if he was a celebrity.

“I’d much rather be a fashion icon than a political icon,” he said.

During my evening with Yiannopoulos, we talked about his $10 million lawsuit against Simon & Schuster, the state of conservative media, the Trump administration, “fake news” and what he would do to improve free speech on college campuses. Oh, and we crashed Fox News anchor Melissa Francis’ book party after our interview.

Yiannopoulos, 32, likes to portray himself as not getting a fair shake by the press. What follows are lightly edited snippets of our wide-ranging conversation arranged by topic:

Milo Yiannopoulos
Milo Yiannopoulos holds up a copy of a legal complaint as he speaks outside the offices of Simon & Schuster publishing company, July 7, 2017 in New York City. (Drew Angerer/Getty Images)
Getty Images

Simon & Schuster

What’s it feel like to file a $10 million lawsuit?

“I wouldn’t have done it just as a publicity stunt because I think there are better ways of getting publicity, and I never want to come across as whiny or litigious. Because I don’t think it’s good. I don’t think it’s very on-brand. I don’t think it’s a good style for me. But, by the same token, they really deserve to have a smack in the chops.”


“Because they broke the contract, and they did so pre-textually. One day they said the manuscript was fantastic, they loved it, they were happy with my hard work, they were looking forward to aggressively promoting it, putting all the marketing muscle of Simon & Schuster behind it. … And then 24 hours later, they suddenly decided the manuscript was unfit for publication. Well, yeah, there was a little controversy around me, but that’s what I do for a living. And not just the emails, but the contract I signed with them specifically referred to me as both a provocateur and as controversial. It’s not like they didn’t know what they were getting into. In fact, it’s why they wanted the book.”

[A Simon & Schuster representative called Yiannopoulos’ lawsuit “publicity-driven and entirely without merit.” On August 9, Yiannopoulos’ company teamed up with the People for the Ethical Treatment of Animals and Carafem, an abortion-pill provider, to sue the Washington, D.C., subway system for refusing to run their advertisements. The American Civil Liberties Union is representing them in their case against the Washington Metropolitan Area Transit Authority.]

Conservative media

“As a conservative, you have so much more of a hill to climb from, the media pretending the book doesn’t exist. Despite the fact I said, selling more than anybody else, to the tiny advances that you get, compared to the number of copies you’re going to sell. Like Lena Dunham and Amy Schumer, are getting three million, seven million, nine million. I got $250,000. Are you f-cking kidding me? What a joke. I’m going to sell more copies than both of them.”

[Dangerous, published July 4, has been on the New York Times best-sellers list for hardcover nonfiction for four weeks. The book is currently ranked seventh. Amazon recently ranked Dangerous 124th on its list of best-selling books.]

Do you think there is a lack of conservative voices in the media?

“In the mainstream, of course, I would.”

What is mainstream anymore?



“Who watches Fox? The average age of a Fox viewer is over 70. If you’re under 55 and you want to watch a current affairs show and you’re right of center, you have nothing to watch on television. Name a show.”

What about [Glenn Beck’s] TheBlaze?

“What about TheBlaze? These are like niche, fringe organizations. I mean, TheBlaze is exclusively directed at evangelicals. The reason Tomi Lahren lost her career is that you’re not allowed to have opinions about certain things and survive with evangelicals. Evangelicals of course, by the way, being some of the people who run CPAC, who don’t like gays as it is. And, me talking loosely, in a way that I didn’t intend, about relationships between older men and younger boys, I’m their worst nightmare. Because they all think gays are pedos already anyway. I start saying something that sounds like that, I literally become the Antichrist for them. Like, literally. But it’s run by evangelicals. I mean, what’s in it for the rest of us? Who the f-ck watches TheBlaze? I’ve never met anyone who watches TheBlaze. It’s just an overfunded, overtooled network that’s watched by nobody.”

[TheBlaze had 5.3 million unique visitors in June, according to comScore data, which is down from the 13.7 million unique visitors the website had in June 2015.]

I feel like you’re pitching me on the Milo Network …

“That’s why I’m so mad at Simon & Schuster because the Milo Network has been put back a year or two as a result. I have 50 hedge fund managers who want to write colossal checks for somebody who could be the next right-wing Bill Maher. And they don’t care if they see the money again because they just want to see that it’s possible and open up the market because 40 to 50 percent of the American population simply isn’t being served by the media industry, right? They have nothing to read, nothing to listen to, nothing to watch, nowhere to go. Like, nowhere to go. Like, nothing. If it weren’t for Simon & Schuster, I could’ve raised hundreds of millions of dollars and at really good terms, this year.”

The Trump Administration

Are you in regular contact with anyone in the Trump administration?

“Okay. I have lots of friends who are in the administration, and lots of friends who are in the campaign, and lots of friends who are around that universe. Obviously, Steve [Bannon] … brought me into Breitbart and is one of the most brilliant people I’ve ever met. He’s just like a force of nature, like a juggernaut. He’s an incredible person. I have a lot to thank him for. One of the things that really pushed me off the deep end with the media is watching what they did to Steve Bannon.”


“They were so scared of him, because why? Because he’s effective. And he wins. He got Trump in the White House. Nobody else did. Bannon did it. Nobody else did it. Steve Bannon put Donald Trump in the White House. And they hate him for it. So, what do they do? Ramp up the racist, ramp up the sexist, what’s the next new thing? White nationalist, white supremacist. On the basis of zero evidence. This is a guy who brought in Raheem Kassam, the Muslim-named, brown editor of Breitbart London. Me, the gayest guy in journalism. In a company entirely staffed by Jews, like every senior editor of Breitbart is Jewish. Alex, the [editor-in-chief], is Jewish. There’s a Breitbart Jerusalem vertical.”

Midway through our interview, a young woman in her 20s or early 30s walking on the street spotted Yiannopoulos through the restaurant window and waves. He got up from the table, went out to the sidewalk and hugged her. I heard her say how big a fan she is of his. He came back to the table nonchalantly. “She is a plant, right?” I asked. He laughed and said “I don’t have to do that. What was I saying?”

“Fake News.”

What do you think is the biggest misperception the press has about you?

“Well, they don’t know me at all. Because, they don’t come to my shows, they haven’t read my book, they don’t read my columns. When they do read my columns, they deliberately misrepresent WASP-ish, satirical polemic as hateful diatribe. You know when I write a column like, Birth Control Makes Women Unattractive and Crazy, it’s like laugh out loud funny. It’s like, ‘What the f-ck is going on here?’ and they think that I’m some kind of like basement dwelling vlogger like, spitting out hate against women. One paragraph into the story, when I make a joke about black d-ck or whatever, it’s pretty f-cking obvious that’s not the case. And, they know that, but they write the stories up anyway.”

So, they take your satire as straight news?

“Exactly. And, NBC News, out of nowhere, on the basis of no evidence for no reason, called me a white nationalist. Like, f-ck those guys, right? On the basis on what? Ask a white nationalist if they’re a white nationalist and they’ll say, ‘Yeah. I’m a white nationalist. I’m here for white nationalists.’ And, I’ll be like, ‘No.’ And in about seven public speeches, viewed by 500,000 people on the internet this year, I said ‘White pride isn’t the answer,’ and ranted for 10 minutes. But, no one’s ever seen that, because they don’t want to go look because if they go look, they have to admit to themselves that I’m not. They would rather just call me a name and not read anything. This is a structural problem with American media.”

“For the most part in left-leaning places, I think, they’re doing to me what they’ve done to conservatives before as well, pretend they don’t exist until they’re too big to ignore them and try and take them out. I’ve slipped back because of what happened at Simon & Schuster. They think they’ve got one up on me. So now they’re just going to ignore me. And if I get big enough again, they’ll come for me again.”

Free speech on campus

If you were dean of a college, what would be your approach to free speech on campus?

“Oh. Well, I would invite communists, Nazis, feminists, men’s rights activists, black supremacists, white supremacists and everything in between. Don’t just want this festival of trolls and circus freaks. I want the most serious academics in every discipline. But I also want people on the very fringes of everything. Because I’m a classical liberal, and I think that if you get to university, you have demonstrated that you have the critical faculties enough to distinguish fact from fiction, garbage from sense. And I want people to be exposed to the full range of opinions, including the offensive nonsense stuff at the end. The people who hate me are on the right. You know the white nationalists and Nazis who hate me, because they do.”

“The funniest thing about me getting called these names, because Daily Stormer, which is like the New York Times of Nazis, f-cking hates me. They said I was the number one enemy to their movement. They declared a holy crusade against me and nobody will report it.”

After the interview, Yiannopoulos and I went to a bar next door to attend Melissa Francis’ book party for Lessons from the Prairie. Francis was on Little House on the Prairie for two seasons. Today Show co-host Kathy Lee Gifford attended the party, too. Yiannopoulos walked the room for about five minutes as if looking for an audience to hold court, and then returned to the Italian restaurant. He had a video interview with a British tabloid reporter next.

Update: The story has been updated to include Dangerous’ rank on the New York Times best-sellers list for hardcover nonfiction.

The InsideHook Newsletter.

News, advice and insights for the most interesting person in the room.