This would indicate that:

(a) That more than just the top bosses had "possession" of these photos and
(b) That the amount of copies of these photos circulating would almost certainly mean that one of them would have leaked.

Like, did Giancana just make a bunch of copies and hand it out to all of his Taylor Street guys? At least a dozen guys from that crew went to jail in the late sixties/early seventies and they never exploited it once?

I don't believe solidly one way or another if Hoover was a cross-dresser and if the mob had photos proving it they would have played that ace at some point.