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The only surprise in Milo Yiannopoulos’ flameout was how fast it happened

Click to play video: 'Milo Yiannopoulos blames media for ‘politically motivated witch hunt’ to hurt him' Milo Yiannopoulos blames media for ‘politically motivated witch hunt’ to hurt him
WATCH ABOVE: Controversial alt-right personality Milo Yiannopoulos says he doesn't believe that any journalist actually thinks he supported pedophilia but instead he believes they were out to hurt him – Feb 21, 2017

Four days, 96 hours. That’s how long British writer, speaker and comedian — those are the most neutral descriptors I can think of — Milo Yiannopoulos lasted as part of the mainstream American political dialogue. Milo, as his fans and enemies alike call him, lived by the free speech sword. His career died by it on Tuesday. It’s unclear if he can recover.

READ MORE: Milo Yiannopoulos resigns, apologizes and talks about past abuse

Many will say it was his reckless comments about child abuse that did him in. And it was certainly the straw that broke his back. But I have a sneaking suspicion that the horrific comments, which I’ll recap below, aren’t what will really stick to him. No, Milo’s career may eventually be shown to have died when he took to the airwaves on HBO.

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A brief recap for those just joining us: Milo is a tech expert and journalist who became famous at Breitbart News via his use of social media, essays and speaking engagements, where he became known for, and overtly portrayed himself as, being utterly politically incorrect. He’s said offensive and impolitic things about, well, everyone: Muslims, gays, trans people, feminists, and basically every ethnicity conceivable.

WATCH: Milo Yiannopoulos issues statement following Breitbart resignation

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EXTENDED: Milo Yiannopoulos issues statement following Breitbart resignation – Feb 21, 2017

I confess to not fully understanding the Milo phenomena, if we can call it that. He has a very loyal army of followers who claim he is a necessary antidote to free-speech stifling progressives run amok, particularly on campus. To others, he’s simply a bigot hurling hate speech and invective for his own enrichment, gussying up a broken, bitter personality by adopting the mantle of free speech warrior. To me, he was both. I liked it when he shattered the safe space delusions of what the alt-right call “snowflakes” and I’d cringe when he’d go too far into personal attacks or outright hatred. But it wasn’t hard to reconcile these behaviours. It was who he was.

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READ MORE: UC Berkeley in lockdown amid protest against Milo Yiannopoulos

As his fame grew, the controversies accumulated. His events were often shut down by protesters, sometimes violently. He was banned from Twitter for abusive behaviour. He also signed a book deal with a major publisher and was invited to speak at CPAC, the biggest right-wing political event in the United States — two major victories for Milo and absolute steps into the mainstream. He also received a plum invitation, to join HBO host Bill Maher’s show Real Time for a panel chat.

And that’s where things began to go badly for Milo.

Milo was on Maher’s panel with three other guests: comedian Larry Wilmore, former U.S. naval cryptanalyst and counter-terrorism expert Malcolm Nance and former Republican Congressman Jack Kingston. It was manifestly clear from the outset that Milo was simply out of his league. He tried to roll out his usual swagger but up against successful, accomplished people — adults, to be blunt about it — the Milo shtick didn’t work. He looked shallow and nervous, particularly when engaged by Nance.

It was a revealing few minutes. While building his fame, Milo always controlled the terms. His audiences were generally friendly, and his targets couldn’t offer much fight. He was punching down, in other words. But Wilmore and Nance aren’t easily offended social justice warriors comfortably ensconced in the artificial bubble of campus life. HBO is not a lecture hall packed with a friendly crowd. Milo was desperately out of his depth. It showed.

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Then there was the second, more dramatic disaster: old interviews with Milo resurfaced that seemed to depict him saying that, in some circumstances, it is acceptable for an adult man to have a sexual relationship with a “boy.” The interviews weren’t new; I’d first heard of them months ago. But with his new stature came new scrutiny, and critical mass was reached. Milo’s speech was cancelled, his book deal scrapped and on Tuesday, he resigned from Breitbart, apparently to stave off a revolt in the newsroom.

READ MORE: Milo Yiannopoulos book ‘Dangerous’ cancelled by publisher

Milo says the tapes take his words out of context, and that some of the recordings were deceptively edited. He also says that he was speaking in gay community terminology, where “boy” does not necessarily mean literal boy, but simply a younger, less sexually experienced man. But he also acknowledged not having proper care when speaking on sensitive matters, and said his own experiences as a molestation victim led him to believe he could say whatever he wanted on the topic without fear of compromise. He also insisted that the recent criticism of him was orchestrated and co-ordinated by his political enemies. It was, he insisted, a campaign to silence him.

WATCH: Milo Yiannopoulos appearance turns to chaos at UC Berkeley. Hena Daniels has the latest from New York.

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Milo Yiannopoulos appearance turns to chaos at UC Berkeley – Feb 2, 2017

Well … yeah. Milo’s naivety and inexperience in the real world, outside of friendly campus gigs, was again on full display. Of course his critics waited and watched and chose a good moment to publicize what they had. How can Milo, who portrays himself as a world-class cynic, someone above all the typical BS of polite society, be surprised by the effectiveness and ruthlessness of his enemies?

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Because, as we saw on HBO, he’s actually not that effective a public speaker or critic. He can thrive, but only one as artificial as the campuses he finds so risible. Taking on fragile campus progressives, it turns out, was lousy preparation for life as a serious, for-real political operative. That’s why I’ve had headaches that lasted longer than Milo’s moment in the mainstream.

He says he’s not done. Another publisher will print his book, he promises. He says he’ll launch a new media venture and be back in a matter of months. Perhaps. But a comeback will take more than just living down the current controversy. It’ll mean learning how to fight adults on adult terms. If he can’t or won’t do that, he’ll spend the rest of his time in the obscure corners of the alt-right web that birthed him. That would be a shame, in a sense. But it would be a failure entirely of his own making.

Matt Gurney is host of The Morning Show on Toronto’s Talk Radio AM640 and a columnist for Global News.

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