Milo suffers from the occupational hazard of a professional provocateur. If you constantly ad lib in interviews and Q/A sessions, if you make a career of making outrageous statements, you're liable to become ensnared in your own rhetorical spiderweb. You keep spinning that web until you have no escape route. All the threads are sticky.
He gets away with lots of stuff because he's a pretty boy, because he's gay (which is chic), and he can speak the pop culture jive. If he looked like John Lennox, he wouldn't have the same following. He wouldn't have any following at all. And in 5 or 10 years he'll probably be washed up because his pretty boy looks will have faded.