Alex Gates (Jack Nicholson) is a wine dealer who is having a tough time of things. His business is not nearly as strong as he would like it to be, or as strong as he tells his wife Suzanne (Judy Davis). His marriage is also suffering, and he has a very poor relationship with his step-son Jason (Stephen Dorff). With things going so badly, Alex decides to try to do something to change his fortunes. His plan: steal an expensive diamond necklace, with the help of his partner in crime Victor Spansky (Michael Caine). He also intends to dump his wife to be with his mistress, Gabby (Jennifer Lopez). When Suzanne unknowingly interferes with the planned sale of the necklace, things become a bit more complicated.