How about the dumbest boss ever....Joey Merlino has to be close. I know I will get ripped for this but come on the guy wasn't the smartest. He basically stole for a living. He didn't reinvent the wheel when he was boss. He just took what he wanted. And lets not forget that he made Ralph Natale and then makes him boss. Natale should have never been a boss. He wasn't even a made guy until Merlino. And then Natale helps bring Merlino down. I know he didn't get a lot of time and he kept is mouth shut and all. Thats all well and good but the man was basically a soldier at best as far as smarts go. He was around the life always. He knew what he needed to do to get by. I am not saying he is the dumbest gangster. Not by far! But dumbest boss...hes gotta be in the top 5...at least! He also just loved those cameras! Which is stupid in this life. I can see him in a reality show in 20 years. People feared him though in a lot of ways. I just think of him as not being the smartest man.