Caan plays Frank, a thief who specializes in safe cracking and who prefers only to steal hard-to-trace valuables such as diamonds and cash. Frank is working hard to reach his goal of retiring and leading a normal life, but when he decides to take a shortcut to reach his goal sooner, he risks losing everything.
This film provides examples of:
- Bittersweet Ending: Frank successfully kills Leo and Attaglia, but he has cut all ties with Jesse and their adopted son and will likely never see them again.
- The cut, unfilmed ending had Jesse eventually find Frank.
- Break Her Heart to Save Her: What Frank ultimately does to Jesse.
- The Cameo: William Petersen has a small role as a club bouncer.
- The Dragon: Attaglia to Leo.
- The '80s: Right down to the soundtrack by Tangerine Dream.
- Honor Before Reason: Frank loses everything he cares about - and probably loses out on a much better albeit still criminal life - because of his my way or the highway attitude and refusal to work and play along with Leo and his gang.
- It's Not You, It's My Enemies: Frank orders Jessie to leave him after Leo threatens her and their child. He doesn't explain himself at all, making this a harsher but more effective use of the trope.
- Politically Incorrect Hero: Frank issues a slew of ethnic slurs at the adoption agency that would, if anything, make the agency less willing to allow him to adopt.
- Shown Their Work: In the director's DVD commentary, Mann explains that former Chicago thieves and police detectives consulted for the movie and even acted in several of the roles (most of the former thieves portrayed cops in the film, and vice versa), lending their technical expertise and knowledge of real-life criminal and law enforcement tactics to enhance the accuracy and realism of the film.
- Tracking Device: Chicago police hide one inside the bumper of Frank's car, and follow it out of town to what they think is his next score. Only problem is he found it, so they're following a Greyhound bus to Des Moines, which has the tracker inside a package in the cargo area.
- Villain Protagonist: Frank.