It is the Prohibition Era of the 1930s when mobs ruled big cities who still had a thirst for outlawed liquor. Mob leader Leo O'Bannon (Albert Finney) has had a tight control over the city for years. Within the gangster group Johnny Caspar (Jon Polito) tries to take the liquor market from Leo. Tom Reagan (Gabriel Byrne) is Leo's right-hand man. But as Johnny rebells against Leo, he tries to enlist Tom to kill Leo's girlfriend's brother Bernie Bernbaum (John Turturro). To kill him, Tom must take Bernie into the forest to Miller's Crossing. However, Tom has started an affair with Leo's girlfriend, Vern Bernbaum (Marcia Gay Harden) so he is torn between loyalties. He doesn't really want to be working for either rival. But to carry out the killing would mean he would be switching sides and working for another mob boss and against his old mob boss. Tom is caught in a delimma for which he has an internal struggle.