Gavin Banek (BEN AFFLECK) and Doyle Gipson (SAMUEL L. JACKSON) are two men in a hurry to get somewhere when they're involved in a minor traffic accident. Gavin, a 29-year-old lawyer, needs to get to the courthouse for a probate hearing to deliver documents that will transfer control of a wealthy but deceased man's $107 million estate over to his law firm.
Unbeknownst to either man, Doyle, an insurance agent and recovering alcoholic, is also headed for the courthouse, but for different reasons. His estranged wife, Valerie (KIM STAUNTON), is planning to move their two young sons across the country to get away from him. Doyle needs to attend a custody hearing where he plans to announce that he's just been approved to buy his first house that he going to allow Valerie and the kids to use so that they won't move.
Unfortunately for him, the accident leaves his car out of commission, and Gavin, who gives him a blank check to pay for any inconvenience, refuses to give him a lift, telling him "better luck next time." When Gavin gets to the courthouse, however, he realizes that in his confused rush at the accident scene he accidentally left a folder containing one of the important documents needed for the transfer.
The judge gives him until the end of the day to file them with the court, and Gavin then lies to his bosses,
Stephen Delano (SYDNEY POLLACK) and Walter Arnell (RICHARD JENKINS), the former who just so happens to be his father-in-law, that everything went fine. Confiding in his assistant, Michelle (TONI COLLETTE), Gavin tries to figure out what to do.
Meanwhile, Doyle is late for his hearing and thus loses custody of his kids and most any chance of Valerie staying in the city. When Gavin eventually tracks him down, Doyle says he threw the folder away and heads off to a nearby bar, much to the chagrin of his AA sponsor (WILLIAM HURT), but not before retrieving the papers after realizing how much Gavin wants them.
He's about ready to return them when Gavin leaves him a nasty message stating that he's ruined his financial status thanks to the work of a hired gun (DYLAN BAKER) who can do such things. From that point on, and as Gavin's greedy wife Cynthia Banek (AMANDA PEET) urges him to continue in the firm's corrupt ways so that they can maintain their lifestyle, the two men get into an escalating match of tit for tat that eventually reaches extreme and even dangerous levels.