For the bank robberies sequence, Tyler Hoechlin (Michael Sullivan, Jr.) had to learn to drive, something he was only too happy to do. Hoechlin mastered it all easily, but, just to be on the safe side, a stunt driver was sitting in the back, with his own set of driving controls.
The movie is loosely based on actual events, and a real enforcer for mobster John Looney, who was betrayed by him.
After his success with his directorial debut Beauté américaine (1999), Sam Mendes was the flavor of Hollywood and was sent all the top scripts. Some of these included Un homme d'exception (2001), K-PAX - L'homme qui vient de loin (2001) and Noeuds et dénouements (2001). He was attracted to La voie de Perdition (2002) because it was a film of few words, something of a change after the wordy screenplay of Beauté américaine (1999).
In order to court Paul Newman to appear in the film, Sam Mendes paid the actor a visit at his apartment. The first thing Newman said to him when he opened the door to Mendes was "Jesus, you're young".
To create a villain that could challenge the physically imposing Tom Hanks, director Sir Sam Mendes wanted Jude Law to seem rodent-like.