Top Definition
People in suburbia CT that think listening to 50 Cent and driving an SUV/Luxury car with 20" rims and wearing pants that sag off their ass qualifies them as a gangster.

Actual hard parts of CT are New Haven, Hartford, New London city (some parts), and Bridgeport.

Anyone in backwoods city such as Griswold, CT that think of themselves as "Gangstas" need to search UrbanDictionary for: Connecticut Backwoods Gangsta
Jon: Hey, look at Tommy over there. He used to chill with us, now he's all Rocawear with it and such.

Tim: Yea, that Casper is a Connecticut Gangster now. One day Hollister and now he's all Sean John.
by mooseface980980 March 31, 2009
1 more definition
Any person who works or does business in the State of Connecticut and is successful over an extended period of time.
I have been living and working in Connecticut for more then eight years, and I still haven’t ended up loosing my shirt; but only because I am a Connecticut Gangster.
by Arrowwood_13 January 21, 2010

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