A partial account of the life of James 'Whitey' Bulger is presented. This phase of his story begins in 1975 when his gangster activities are largely confined to the South Boston neighborhood where he grew up, there where his group, the Winter Hill Gang, are the kingpins of such criminal activity. John Connolly, an FBI agent recently returned to Boston and a childhood friend of Whitey's state senator brother, Billy Bulger, from the neighborhood, approaches Whitey with a proposal: to act as his snitch against other Boston mobsters, most specifically the Angiulos of North Boston, in return for protection against any FBI action against himself, with only a handful of people within the Bureau in the know. Although reluctant at first in not wanting to be caught or thus identified as an informer, Whitey eventually agrees following a specific incident. The effect of their agreement on their professional and personal lives over the next twenty years is presented, as Whitey's criminal empire is allowed to flourish with the unfettered elimination of his competition, as Whitey does whatever he feels he can and wants without FBI retribution to protect his own interests, and as those in the know within the FBI begin to question whether Whitey has been of any real use to them.