I think you have to differentiate the dumbest gangster with those that did the dumbest things. Capone was a great organizer that was able to generate hundreds of millions of dollars back n the 1920's. A ruthless, street smart mob boss that successfully fought off his rivals. But one of the dumbest things he did was fail to file income taxes. Unable to intimidate the judge and jury, he goes to prison and dies insane from untreated syphlis.

Yes, add Gotti to the list. Good soldier, capo, enforcer, but a dumb boss. Castellano: good businessman, but allowed the FBI to actually enter his home and bug his kitchen.

The smart ones are the Gambinos and Bonnanos - the one's that died of natural causes.

"After all, we are not communists"

Christopher Moltisanti: You ever think what a coincidence it is that Lou Gehrig died of Lou Gehrig's disease?

Tony Soprano: Yeah well, when you're married, you'll understand the importance of fresh produce.