Wasn’t his whole life a gamble?

Gangster James J. “Whitey” Bulger allegedly told federal authorities after his arrest that he regularly visited Las Vegas during his time on the lam.

And he “won more than he lost,” he said.

In court documents filed Monday, federal prosecutors said Bulger liked to play the slots during his visits.

Bulger also told officials that he crossed the Mexican border at San Diego and regularly purchased prescription drugs in Tijuana. Former Bulger right-hand man Kevin Weeks has said in the past that Bulger used to boast about how easy it was to get prescription medicine in Mexico.

The FBI also said Monday that Bulger admitted to returning to Boston multiple times in disguise while “armed tot he teeth” in order to “take care of some unfinished business.”

Bulger did not elaborate.

About The Author

John Guilfoil is the editor-in-chief of Blast: Boston's Online Magazine and the Blast Magazine Network. He can be reached at [email protected]. Tweet @johnguilfoil.

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