Nowadays most young and future wiseguys are just wannabe gangsters who constantly try to act tough. Most of these kids grew up in suburban areas and decent family homes. At what period do you think that mafia guys were the toughest? Maybe around 1920s after the mass immigration of italians?

Early 1900's. When the conditions they lived in were horrible as well as poverty.

I guess modern day gangsterism is indeed more about white collar crime than street hoodlum stuff. Online scams, credit card fraud and stuff like card 'skimming' probably requires more brains and sneaky tactics in this age of high-tech surveillance.

of course, late 1800's and early 1900's. Look at Movies like 'Gangs of New York', real toughguys