Nick is in love with his pen-pall Ashley Mercer that he never personally met and has known her through a magazine, letters, and photos.
In Michigan, the car thief Rudy Duncan and his cellmate Nick Cassidy, who killed a man protecting his girlfriend Millie Bobeck, are to be released in a couple of days. Things don't go as planned with a number of plot twists and double crosses.
Rudy is violently coerced to cooperate with a Christmas Eve casino robbery scheme that Gabriel and his gang have been planning with Nick's casino knowledge as the key. Nick had spoken of his previous employment in security with an Indian casino and Rudy finds himself involved with Ashley's criminal gun runner brother Gabriel (Gary Sinise). When Rudy Is released the next day from prison he recognizes Ashley waiting outside the prison for Nick and Rudy takes his place and pretends to be Nick. Nick is killed defending Rudy during a prison riot. Rudy is looking forward to returning to his family and having a fresh cup of hot chocolate. Nick has a number of pictures from a romantic correspondence with a woman named Ashley he has never met but is waiting for his release. After being imprisoned for six years on a grand theft auto charge, Rudy Duncan (Ben Affleck) is days away from release as is his cellmate Nick (James Frain) who is is serving a two year sentence on a separate charge.
