I’m listing this one first because it’s so tantalizing. As Omar Little has taught us, the only thing more fascinating than a heartless killing machine is a heartless killing machine with a proclivity for the Pet Shop Boys. Unfortunately, the evidence is flimsy. Exhibits follow.
Exibit A) Howie Carr, who I suspect may be a bit of a loon, alleges in his book “The Brothers Bulger” that Whitey started out as his criminal career as a teenage gay hustler given to robbing his tricks. But even if that’s true that doesn’t make him gay so much as a violent sexual opportunist. You don’t suck dick for money because you really love sucking dick; you suck dick for money because you want/need money. Otherwise, you’d do it for free (sorry if anybody thought crack addicts are super-horny).
Exhibit B) He stayed at a gay hotel a couple of times. The hotel’s owner, a friend of Whitey’s once tried to scare an employee from testifying against him by invoking Whitey’s name. This proves nothing, except that Whitey was surprisingly cool with gay dudes for a thug from South Boston and that the hotel owner was smart enough to know that if you want to scare somebody you better say some scary shit.