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Criminal AssociationPlay
Gangster often implies involvement in organized crime, not just petty theft or solo activities. SlideThe gangster had ties to the mafia.
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Negative ConnotationPlay
The term is viewed negatively and suggests immoral or illegal activities. SlideThat neighborhood is known for its gangster activity.
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Historical ContextPlay
Gangster can bring to mind historical figures like Al Capone, notorious in the 1920s. SlideHe dressed up as a 1920s gangster for the party.