Here's another thing about Trump.
Trump was in New York real estate and construction from the start. There's no way to do that without dealing with the Mafia.
Any smart boss is going to take one look at Donnie and step away. A boss doesn't want to be around a loudmouth who can't be trusted to keep his mouth shut.
So the mobsters Donnie interacted with were the low level goons the bosses could throw under the bus if anything went wrong.
All of Donnie's schemes are crude because that's what he thinks are clever schemes. His smartest mentor, Roy Cohn, died too soon to teach Donnie how to actually act like a winner.