Criminal Career
In 1976, after he gave up on college, Weeks became a bouncer at a popular neighborhood bar, "Triple O's". This was a frequent hangout of the Winter Hill Gang, an Irish-American crime family which was then headed by James J. Bulger. It was here that Weeks first met Bulger, as well as Bulger's Italian-American partner Stephen Flemmi. Beginning in 1978, Weeks began working for Bulger part-time as muscle and a personal driver. Impressed by Weeks' knack for making money and genuinely liking him, Bulger decided to bring him in closer than any other associate. Meanwhile, Weeks turned to running a loansharking business on the side.
In 1982, just four years after beginning to work as part of the Winter Hill Gang, Weeks left his legitimate job and became a full-time mobster in the gang.
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