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You think Biggie Smalls was a true OG? The Notorious One doesn't have anything on Whitey Bulger.
One of the most brutal gangsters ever seen in the Irish-American hood of South Boston, Bulger rules the city's criminal underworld for decades. Of course, he has a little help from his friends: a few corrupt FBI agents, for one.
Aided by his G-men pals, Bulger stacks up a body count that would make Voldemort jealous, dominating everything from drugs to gambling to vending machines. He might be a criminal, but the Whitey portrayed in Black Mass sure isn't common.
Bulger can be considered a "chessmaster" when it comes to crime: he exploits the FBI's informant deal to its maximum benefit.
Bulger can't be considered a "chessmaster" when it comes to crime: he simply lucks into the best FBI informant deal of all time.