New York, early 1960s. Against the backdrop of a vibrant music scene and tumultuous cultural upheaval, an enigmatic 19-year-old from Minnesota arrives in the West Village with his guitar and revolutionary talent, destined to change the course of American music.
During a bitter 1964 Massachusetts winter, young secretary Eileen becomes enchanted by Rebecca, the glamorous new counselor at the prison where she works. Their budding friendship takes a twisted turn when Rebecca reveals a dark secret — throwing Eileen onto a sinister path.
To take down South Boston's Irish Mafia, the police send in one of their own to infiltrate the underworld, not realizing the syndicate has done likewise. While an undercover cop curries favor with the mob kingpin, a career criminal rises through the police ranks. But both sides soon discover there's a mole among them.