Obviously many interpretations of tough, but I'd say:

1- Frank Calabrese, Sr
2- Roy DeMeo
3- Greg Scarpa
4- Sam Gravano
5- Lord High Executioner (for good measure)

Originally Posted By: phatmatress
i see alot of people putting demeo on here. i find him the most interesting gangster and if you want to go as to call him my fav i guess you could do this. he was very psycopathic and cruel but i don't know how tough he really was. he def had a tough stomach. but also killed a man who gave him a black eye. although the line he muttered about the guy who gave him a black eye was "last important thing he will ever do!"

Roy was known as a burly tough guy that was good with his hands, even if he only used his trigger finger and bone saws most of the time...

Also, I believe it was Nino Gaggi that got punched, not Roy. Nino was definitely not a street fighter type.