Gangster/ˈɡæŋstər/ Definition 1 of 3Pro Tip 1/3Criminal Association Gangster often implies involvement in organized crime, not just petty theft or solo activities. The gangster had ties to the mafia. Pro Tip 2/3Negative Connotation The term is viewed negatively and suggests immoral or illegal activities. That neighborhood is known for its gangster activity. Pro Tip 3/3Historical Context Gangster can bring to mind historical figures like Al Capone, notorious in the 1920s. He dressed up as a 1920s gangster for the party.