James "Whitey" Bulger became an FBI official informant (double-crosser, hypocrite, narc, rat, snitch, traitor, turncoat) in 1975, although the FBI refused to admit this until 1997. Nicknamed Whitey because of his white-blonde hair, we think that Josh Brolin should find a bottle of bleach and take on the role of Whitey. We reckon he's a pretty adaptable actor; the man has played both a Goonie and George W. Bush.

Photo by Mikael Jansson.

Stephen "The Rifleman" Flemmi was, as his nickname suggests, another miscellaneous law-breaker from Southie and a friend of Whitey's. Flemmi was a key figure in Whitey's transition from criminal to criminal and FBI informant. Flemmi had been an FBI informant since the 1960s (code name "Jack from South Boston). In 1975, Whitey confided in Flemmi that he had been approached by the FBI and asked Flemmi's advice. According to Black Mass, Flemmi told Bulger to accept a meeting with the Feds. When Flemmi's original FBI handler retired, John Connolly Jr. became Flemmi's handler. We would like Boston native Casey Affleck to put on his outlaw hat and play Flemmi.

Whitey Bulger's FBI handler, the man who convinced him to partner up with the feds, was John M. Connolly Jr. John was also from South Boston—he grew up in the same housing project as the Bulgers and knew of Whitey from a very early age. Keen to move up the FBI ranks, Connolly saw Bulger as his biggest asset. Unfortunately for Connolly Jr., he got rather caught up in his friendship with Bulger and is currently serving a 40-year state prison sentence in Massachussets for second-degree murder. We pick Michael Pitt as our J. M. C. Jr.


Photo by Craig McDean.

As everyone knows, Whitey has a younger brother, William "Billy" Bulger, who chose a different path than Whitey's and ended up becoming president of the Massachusetts senate and then president of University of Massachusetts for a few years. Whether or not Billy helped Whitey elude capture by the FBI from 1995 to 2011 is a rather polemic subject. Our pick for the part is John Francis Daley. The actor is five inches taller than Billy, but perhaps he can stand in a ditch.


Photo by Mitchell Nguyen McCormack.

For our 19-year-old Whitey, we think former child actor Jonathan Lipnicki (the "a human head weighs eight pounds" child from Jerry Maguire) would make an excellent younger Whitey.  

John Connolly first met Whitey during the summer of 1948, when Connolly was eight and Bulger was 19. The story is that Bulger, who already had a reputation in Southy, bought young John an ice cream. Why this act of generosity? Irish solidarity: "Your mother and father are from Ireland, I'm no stranger," is what Bulger purpotedly told Connolly. We think Mason Dale Cotton (aka M.J. Delfino form Desperate Housewives) would make a lovely young Johnny. Look how sweet he is; we'd probably buy him an ice cream, too, if that didn't sound so creepy.