Exposing Milo was a big glownigger op courtesy of the Ewan McMullan-associated
"Reagan Battalion" laundered through Washington Times-subsidiary Vox. It cost him his patronage from the Mercers, which was more or less the only thing he had going for him. Milo was probably expecting some sort of reward after Trump's improbable ascension to the Presidency, or at least some support while he was Thanos-snapped from conventional politics. While Milo may be a gay degenerate pedophile, I can't deny he has a legitimate grievance there.
I mean it doesn't take some sort of genius political operator to predict how an offer of being the VP of Kanye West would go down with Trump, or smuggling "groyper incel cum hunter" Nick Fuentes as part of Kanye's entourage to be seen with Trump and then leaking it to the press.