Dennis (Paul Giamatti) has just been released from prison in Quebec, focused on rebuilding his life and reconnecting with his estranged wife and young daughter. When Dennis arrives home, he discovers that in his absence, his wife has lost patience with him and has told their daughter that he died in prison. Without a home and unable to get a job, Dennis turns to Rene (Paul Rudd), who is now living with Dennis' wife. Rene reluctantly agrees to take Dennis on as a partner selling Christmas trees in New York City during the holidays.

With business struggling, and tensions rising between the two salesmen, Dennis struggles to adapt to his new lifestyle - working hard instead of stealing. Befriending a straight talking local housekeeper named Olga, Dennis tries to prove he is a changed man, but old habits die hard when he has a goal to achieve before Christmas - to deliver a special gift for his daughter.