140: Who the Hell is Milo Yiannopoulos? feat. Bobby Silverman [UNLOCKED]

This episode originally debuted on Sept. 2, 2026, as an exclusive for our supporters on Patreon, where we release exclusive episodes each Thursday. Sign up and listen through our backlog of premium episodes here: patreon.com/postingthroughit

'FEMDOM' Shirts: Pre-order Link

~~~

Milo Yiannopoulos emerged during the alt-right's rise before Trump's 2016 win and went on to be arguably the movement's most famous—or infamous—influencer. A standout in a conservative MAGA space for his flamboyant dress and outspoken enthusiasm for gay sex, Yiannopoulos became a star of Steve Bannon's Breitbart News and helped drive the misogynist "Gamergate" harassment campaign before leading a notorious troll storm against Black comic Leslie Jones. He elicited protests on his "Dangerous Faggot" tour and landed a massive book deal before his comments about adults having sex with minors sent his trajectory in a star-crossed direction involving Kanye West collaborations, turning "straight," and being sent back to England at the hands of a brutal ICE agency he once championed.

Jared and Mike's guest for this episode is Bobby Silverman, returning after previous Who the Hell episodes: Tim Pool, Dave Portnoy, and Michael Tracey. Bob interviewed Milo during the height of his celebrity, and together the three trace his path from his English upbringing to his recent deportation at the hands of frenemy Laura Loomer. So enjoy the limelight while you're in it — because one day you're America's bad boy, and the next you sink to the bottom of the sea, like a sodomy stone.

Transition Music: "Never Outnumbered" by Shaolin Punk