We begin with a sweeping aerial shot of the neighborhood where Whitey was born, raised and reigned: Southie, as South Boston is known, a blue-collar, insular Irish enclave “whose residents valued loyalty to family, neighbors, and neighborhood over all else.” Dissolve to a sepia-toned shot of Southie streets in the 1940s, where a muscular teenager named James Bulger, one of six kids in a working-class family, has already become something of a neighborhood legend: shunning school, running with a bad crowd, with a criminal record from early adolescence on. (“The rest of the Bulger kids were well behaved and studious,” the authors write. “Whitey was just the wild one, the black sheep.”
We throw in some foreshadowing here. One of Whitey’s brothers, William “Billy” Bulger, is already demonstrating the political skills that will one day take him to the presidency of the state senate. We’ll also see another Southie resident, a kid named John Connolly, regard Whitey Bulger with something approaching hero worship.
We move quickly through Whitey’s prison years — he spends nine years in various federal facilities for a bank robbery gone wrong — but we’ll linger long enough to note that Bulger volunteered as a guinea pig in 1957 for a series of experiments with LSD, experiments that produced horrific hallucinations that should make for great footage. (“Suddenly, blood seemed to explode from the walls and drown him. The inmate sitting next to him turned into a skeleton.”)
It’s when Bulger comes out of prison in 1965 that the plot begins to thicken (and the blood begins to flow). Whitey returns to a Boston where the battles between the Irish-dominated mobs of Southie and the Italian-dominated gangs of the North end have left a pile of bodies and a power vacuum that Bulger quickly fills. Moreover, that worshipful kid, John Connolly, has now become a celebrated Boston-based FBI agent with one obsession: crush the power of the Mafia, now that FBI Chief J. Edgar Hoover has belatedly recognized that organized crime does, in fact, exist. Under the theory that “the enemy of the enemy is my friend,” and drawn to the flamboyant lifestyle of these outlaws, Connolly puts Bulger together with a fellow mobster, recruits them as informers and becomes their protector, in effect immunizing them from the law as long as they help him against their common foe — and, astonishingly, tipping them off about prospective informers, which directly leads to at least four killings.