I’ll go Luciano, gambino, gagliano, costello and I will say Benny Lombardo as I think something happened in the Genovese family after Vito and assuming Lombardo was the boss for that time period I think that boss set them up for how elusive they are today. I generally picked bosses who navigated crazy times and largely came away unscathed both from the law and the street. Impressive feat

Dumbest decisions that come to mind: gotti/gravano/decicco killing Paul, Genovese trying to kill Costello, Joe bonanno releasing a book telling the fbi how things worked, Joe Colombo starting a political movement and being a producer on the godfather, Michael mancuso attacking shelved members at a funeral. Most of these are smart people doing stupid things but in the grand scheme completely idiotic in the history of the mob.