James Joseph "Whitey" Bulger Jr. was an American organized crime boss who led the Winter Hill Gang, an Irish Mob group in the Winter Hill neighborhood of Somerville, Massachusetts, a city directly northwest of Boston. On December 23, 1994, Bulger fled the Boston area and went into hiding after his former FBI handler, John Connolly, tipped him off about a pending RICO indictment against him. Bulger remained at large for sixteen years. After his 2011 arrest, federal prosecutors tried Bulger for nineteen murders based on grand jury testimony from Kevin Weeks and other former criminal associates.

Whitey Bulger's father, James Joseph Bulger Sr., hailed from Harbour Grace, Newfoundland, with Irish parents. After settling in Everett, Massachusetts, James Sr. married Jane Veronica "Jean" McCarthy, a first-generation Irish immigrant. The eldest of six children, James Joseph Bulger Jr., was born in 1929. The family moved to Boston shortly after his birth.