While doing some research on Irish Mob Boss James "Whitey" Bulger, I came across this piece of information, which almost parallels the Frank Costello ( Jack Nicholson ) Colin Sullivan ( Matt Damon ) characters from the movie 'The Departed.'



To this day, many Southie residents speak of Whitey with misty-eyed nostalgia, portraying him as their own Irish-American Robin Hood, recalling how he would buy groceries for widows and distribute free turkeys to the poor at Thanksgiving. One story in particular has been repeated so often, it's almost become legend: The Ice Cream Story.

As the story goes, 19-year-old Whitey walked into an ice-cream parlor and spotted three 8-year-old boys standing at the counter. Feeling magnanimous, Whitey offered to buy them all ice-cream cones, but one of the boys balked, saying that his parents told him never to take gifts from strangers.

Bulger allegedly picked up the boy, sat him down on the counter, and looked him in the eye. "Hey, kid," Bulger said, "I'm no stranger. Your mother and father are from Ireland. My mother and father are from Ireland. What kind of ice cream do you want?"

The little boy, who knew of Bulger's reputation as a street tough, was instantly won over. "Vanilla," he said with a smile.

That little boy was the young John Connolly, who would grow up to become an FBI Special Agent and Whitey Bulger's handler in the Top Echelon Program.