Jack Foley, a small-time crook and obviously agitated, walks out of an office building, rips his necktie off and throws it on the ground. He walks into a nearby bank and surveys the lobby for a few minutes. He walks up to a teller's window and informs the woman behind the counter that his accomplice is sitting with her manager and that if she doesn't follow his instructions, the man will shoot her boss. Foley tells her to empty the cash drawer of it's contents, leaving behind the bills on the very bottom of the piles. Foley assures her she's doing a good job, takes the money and walks out, stopping to talk momentarily to the man he identified as his accomplice. The man (a cameo by director Steven Soderbergh) has no idea who Foley is. Outside the bank, Foley tries to start his car, only to flood the engine in his desperation to flee the scene. A police officer, gun drawn, apprehends Foley, who submits without any altercation.
The story jumps to two years before when Foley is a prisoner in Glades Correctional facility in Florida. Playing basketball with other inmates, he looks over the crowd of old-time "lifers" and seemingly reaches the conclusion that he doesn't want to end up like them. He spots a couple of fellow inmates, Chino and Lulu, jogging by. When he speaks to them later, he tells them he knows they are plotting an escape. Another security fence is being constructed just beyond the primary one just beyond the point where they plan to emerge once they've tunneled out. Foley tells them he's going with them in exchange for keeping silent about the breakout. Foley does tell a guard about the plan, telling the man to meet him in the prison chapel that night.
In Miami, Karen Sisco, a US Marshall, has lunch with her father, a retired Marshall himself. He gives her a Sig-Sauer pistol as a birthday gift. He also questions her about a man she's been seeing, Ray Nicolette, another Marshall, who is married. Karen's father doesn't approve and she tells him to drop the subject. She also tells him that she has to go to Glades Correctional to follow up on a case.
Karen arrives at Glades. Also arriving in the prison parking lot is Foley's longtime friend, Buddy. Lulu and Chino have already begun their escape from the prison chapel, while Foley stands watch. The guard Foley had told to come to the chapel arrives and Foley tells him to watch the fenceline. Foley grabs a large vase and hits the guard with it, knocking him out. Outside the fence, Sisco sees the men emerging from their tunnel and alerts the tower guards. Two men escape (one of them is Chino) and two more are shot. Foley surfaces, wearing the guard's uniform and tells the other guards that the tunnel is clear of escapees. Foley approaches Sisco, who wields a shotgun. Foley distracts Karen long enough for Buddy to grab her from behind and they throw her in the trunk of her car; Foley crawls in after her. Buddy drives them away. In the trunk, Foley and Karen have a lengthy conversation, largely about prisoners and movies. Buddy stops under a highway overpass where they are to meet another former convict, Glenn Michaels, who waits with another car. When Foley gets out of the trunk, Karen immediately opens fire with the pistol her father had given her. Foley manages to slam the trunk lid shut trapping her inside. They let her out when she promises to give herself up. They put Karen in the car with Glenn; Buddy and Foley talk for a few minutes about what to do with Karen. Foley is attracted to her, but Buddy doesn't believe she shares his feelings. Glenn suddenly drives off leaving them both behind.
Buddy and Jack return to Miami and go to Buddy's apartment. Foley draws a hot bath and relaxes. Karen appears, gun drawn and finds Foley in the tub. She looks him over briefly and moves in to arrest him when he suddenly opens his eyes and greets her. Karen wakes up in a hospital bed, her father next to her. He asks her what she was dreaming about and she asks him what she said. Her father says, "Hey back." Karen had been unconscious for a brief time and recounts to her boss, Burdon, what happened: in the car with Glenn, Karen, remembering Glenn from a previous prisoner transfer, had persuaded Glenn to leave Buddy and Foley behind. Glenn had complied but an argument had broken out between them about what route to take. With both of them panicky, Karen had grabbed the steering wheel trying to force Glenn to take an exit on the highway. The car spun out of control, hit a water barrier and Karen hit her head inside the car. Karen's inexperienced boss is somewhat incredulous.
At Buddy's apartment, Jack goes through the contents of Karen's purse, finding a picture of her father. Buddy tries to persuade Jack that they need to leave town immediately, however, Jack wants to see Karen one last time. Jack calls her at home and they have a short conversation. She suggest he turn himself in which Jack refuses to do. Buddy suddenly starts talking in the background and Karen recognizes his voice. Their need to escape even more serious, Jack hangs up. On the television is a report about a squatter's camp being raided; Lulu is among the dead. Jack realizes that Lulu could be tied to Chino; in prison, Jack had told Chino about his former wife, Adele, and where she lived. Jack also realizes that it won't be long before the US Marshal's Office finds Adele.
Chino finds Adele's home and goes there, however, Karen has gotten there first and asks Adele if she knows of Jack's whereabouts. Chino starts pounding on Adele's door. Karen gets Adele to stall and when Chino breaks in, Karen arrests and cuffs him immediately. She calls Burdon and asks to be part of the task force looking for Buddy and Jack. Burdon refuses, so Karen asks him if he'll allow her on the team if she brings in Chino. At Buddy's apartment building, Burdon and his team close in on Buddy's apartment and Burdon makes Karen stand watch in the lobby. Buddy and Jack have already exited the room and head down to the parking garage in the elevator. The elevator stops at lobby-level and Karen catches a glimpse of Jack, who sees her also. Buddy and Jack make it to the car and leave.
Jack and Buddy drive to Detroit, intending to catch up with a fellow inmate, Maurice "Snoopy" Miller. They also plan to find another former inmate, Richard Ripley, a wealthy businessman who'd been serving time for embezzlement. While incarcerated, he'd spoken to Glenn about a small fortune he had in uncut diamonds that he kept in his Detroit home. Glenn, however, didn't keep the information secret and Snoopy also intends to rip off Ripley as well. While driving in a limo around Detroit, Snoopy tells Glenn that he's taking over the operation of the heist. Glenn is initially resistant but quite intimidated by Snoopy. Snoopy also demands that Glenn accompany them on a job where they'll kill a transvestite who competes with Snoopy over drug-dealing territory. Glenn does so and the job turns out to be more violent and terrifying than he ever thought. He goes with Snoopy to the Kronk Gym where Jack and Buddy meet up with them. They all agree to meet at a boxing match the next night to discuss the plan to steal Ripley's fortune.
Karen arrives in Detroit and talks to an associate about finding Jack. The agent, Raymond Cruz, in the midst of cleaning up the crime scene left by Snoopy and Glenn earlier in the day, tells her he'll get an address. Karen goes to Snoopy's home and talks to his sister, Moselle, who says she hasn't seen Maurice for several months but he may show up at the boxing matches at the State Theatre the next night. Also at the house is Kenny, Snoopy's brother-in-law. He corroborates Moselle's story and sends her to the store. After Moselle leaves, he tries to force himself on Karen, who hits him with a compact police baton and leaves.
Back at her hotel, Karen fends off the advances of a few businessmen at the hotel bar, pointing out to one of them that she knows he's married. Foley quietly appears & they share a drink together. They go back to her room and have sex. Karen leaves the bed and begins to question Foley's motives in having sex with her. He assures her that he was not out for a one-nighter. In the morning, he's gone and has left the Sig-Sauer pistol he'd taken from her in Florida.
Glenn goes with Maurice to the State Theatre where they watch boxing bouts. Glenn asks to be excused to use the mens room and quickly bolts out of the State and, while trying to hotwire the car Maurice had taken from him, finds Karen waiting for him. Glenn explains that he's really frightened of Maurice & just wants to get away from him. He also tells her that they're planning to rob Ripley's house. Karen lets Glenn go.
Jack and Buddy case Ripley's house. While they sit in the car, Jack remembers meeting with Ripley at his Miami headquarters; in prison, Ripley had offered Jack a job with his corporation after he'd gotten out. Jack is angry to find out that Ripley expects him to take a lower-waged job as a security guard. Jack is furious, thinking Ripley owes him more because he'd protected him in prison. Ripley coldly counters by saying that Jack is a repentant criminal and not worthy of gainful employment. Jack is hustled out by security and walks toward the bank he robs in the first scene.
After the fights at the State, Maurice, Jack, Buddy and Maurice's partners, Kenny and a hulking thug named White Boy Bob. Karen follows them. They drive to Ripley's mansion where Bob, posing as a plumber, forces himself in over the objections of Ripley's housekeeper, Midge. Maurice asks where Ripley is, Midge tells him he's in Florida for the winter. The crew forces her to take them to Ripley's safe in his bedroom. Maurice charges Foley with checking the other rooms in the house. In Ripley's closet, Maurice finds the safe behind some suits. He, Kenny & Bob try to shoot it open; before they can open fire on their second try, Midge tells them the combination is Ripley's birth date. When they get the safe open they only find Ripley's hairpieces. Maurice leaves the room, looking for Foley.
Jack enters Ripley's office and finds Ripley on hold with 911. Buddy finds them both and Jack mentions that he knows that Ripley has hidden his stash of uncut diamonds in the large fish tank in the office. Jack has Buddy retrieve them and take them out to the van, believing they can slip away before Maurice finds them. Out at the van, Jack has an attack of conscience, believing that Maurice is going to kill both Ripley & Midge, possibly raping Midge first. he tells Buddy to take the diamonds and go. Buddy give him a pistol and drives off. Foley reenters the house and goes up to the bedroom. Kenny is in bed with Midge, forcing himself on her. When Foley calls to Midge, Kenny shoots through the door with his sawed-off shotgun, missing Foley. Foley rushes in and shoots Kenny dead, something he's never done before. As Foley makes his way back to the main staircase, he's stopped by Bob. Bob begins to trot up the stairs, trips, and kills himself when his pistol goes off under his chin. Maurice rushes to the scene, shooting at Foley. When they both run out of shots, they begin to fight, Maurice quickly gaining the advantage with his boxing skill. Foley finds Kenny's gun, Maurice seizes Bob's, but isn't faster than Foley, who shoots him dead. Karen also shows up, telling Jack to surrender. Jack, not wanting to go back to prison, wants Karen to kill him but she refuses, shooting Jack in the leg. Jack is tackled by another cop and handcuffed.
Within a few days, Jack is due to be transported back to Florida to face charges associated with his escape from Lompoc. He's put into a van that Karen will also ride in. Before they leave another prisoner, Hejira (a cameo by Samuel L. Jackson), is also put into the van. Jack asks him where he got his name; "Hejira" is the Arabic term for the prophet Muhammed's 7th Century flight from Mecca. Hejira goes on to tell Jack that he's escaped from prison at least nine times. Jack thinks that Karen put Hejira into the van with him because they'd "have a lot to talk about" during the long drive to Florida. They drive off, Karen smiling in the front seat.
(This summary of the movie is not long enough to be suitable as a synopsis. Please add more information to complete the synopsis.)
The story revolves around the relationship between a career bank robber, Jack Foley (George Clooney), and a U.S. Marshal, Karen Sisco (Jennifer Lopez). They are forced to share her car trunk during Foley's escape from a Florida prison. After he completes his getaway, Sisco chases Foley while he and his friends - his right-hand man, Buddy (Ving Rhames) and Glenn (Steve Zahn) - work their way north to Bloomfield Hills, a wealthy northern suburb of Detroit. There they plan to pay a visit to shady businessman Ripley (Albert Brooks), who foolishly bragged to them years before about a diamond stash at his mansion. But a vicious criminal (Don Cheadle) who also spent time in jail with Jack and Ripley, is planning on hitting up Ripley's mansion with his crew, consisting of (Keith Loneker) and (Isaiah Washington), as well. The question of whether Sisco is really pursuing Foley to arrest him or for love adds to "the fun" Foley claims they are having.