Kevin Caffery (MARTIN LAWRENCE) is a professional thief with high tastes in both exquisite women and valuable loot. Thus, it comes as no surprise that he hits on Amber Belhaven (CARMEN EJOGO), a beautiful young woman who's being forced to sell a piece of art at an auction to pay off her hotel bill. The two end up in bed after Kevin lifts the purchased piece, and in turn, she gives him a unique ring that her father gave her.
Since she has no problem with his occupation, Kevin heads off with his partner-in-crime, Berger (JOHN LEGUIZAMO), to knock off a presumably unoccupied house owned by Max Fairbanks (DANNY DeVITO), a ruthless, Boston billionaire who isn't supposed to be in the home due to a bankruptcy ruling. He is there, however, with Tracey Kimberly (SASCHA KNOPF), a.k.a. Miss September, his latest in a series of flings he's carried out behind the back of his upper crust wife, Lutetia (NORA DUNN), that have also included Gloria (GLENNE HEADLY), his personal assistant, sometime in the past.
Accordingly, Max catches Kevin in the act and after the police arrive, he decides to claim that the ring Amber gave Kevin is actually his. The police obviously believe Max, but Kevin escapes from them on the way to jail and decides he can't let the billionaire get away with robbing him, especially when he's ribbed by Uncle Jack (BERNIE MAC), the man who raised him and serves as his loot launderer. Thus, he and Berger enlist the aid of Shelly Nix (GQ), a computer hacker who quickly tracks Max's every move and intercepts every communication.
As Kevin repeatedly breaks into Max's homes and attempts to steal back his ring, the billionaire enlists the aid of his head of security, Earl Radburn (LARRY MILLER), to catch the thief, much to the chagrin of Max's longtime lawyer, Walter Greenbaum (RICHARD SCHIFF). With foppish detective Alex Tardio (WILLIAM FICHTNER) arriving on the scene and believing that Max and Kevin are involved in an insurance scam, the two men continue in their battle over possession of the ring.