What crews were the most feared and what crews were the richest? We always hear that there are two types of gangsters. The ones who are great businessmen that make a lot of money for themselves and the family but don’t get their hands too dirty. And the ones who are the opposite. The gangsters who might not make as much money as others but are feared. Very rarely do you see someone who is both. The DeMeo crew is one of the most feared crews to ever exist. I think finding crews that collectively made huge amounts of money would be tougher. In the Italian and Italian American Mafia.