Inspired by actual events, Money Fight describes the plight of a young fighter who learns the hard way that the driving force behind a worthwhile victory is a valiant purpose.

In 1912, the notorious and violent prisoner Robert Franklin Stroud is transferred to the Leavenworth Prison convicted for murdering a man. When a guard cancels the visit of his mother, Elizabeth Stroud, due to a violation of the internal rules, he stabs and kills the guard and goes to trial three times. He is sentenced to be executed by the gallows, but his mother appeals to President Woodrow Wilson who commutes his sentence to life imprisonment. However, the warden, Harvey Shoemaker, decides to keep Stroud in solitary for the rest of his life. One day, Stroud finds a sparrow that has fallen from the nest in the yard and he raises the bird until it is strong enough to fly. Stroud finds a motivation for his life raising and caring for birds and becomes an expert in birds. He marries Stella Johnson and together they run a business, providing medicine developed by Stroud. But a few years after, Stroud is transferred to Alcatraz and has to leave his birds behind.

Leroy Lowe, grand dragon of the Texas Ku Klux Klan confronts everything he's been taught to hate when he's sentenced to three years of hard labor on a prison work farm, where Warden Merville, dead set on rehabilitating Leroy, chooses Emilio, a Hispanic field worker imprisoned for fighting for labor rights, to be his cell-mate. Leroy, confined in a small cell with the enemy, far from the KKK comrades who deserted him, finds the chatty Emilio slowly chipping away at his anger and prejudice. His weekly rehabilitation meetings with the warden, barely tolerable as the man drones on about farm labor and field crops, take on a different meaning when Madalena, a beautiful Mexican maid is hired to clean the warden's office. An unconventional love story develops that opens Leroy's eyes to the possibility of a different life. And a man who was a born and bred racist finds himself heading down a completely different path to salvation.

Paul "Wrecking" Crewe was a revered football superstar back in his day, but that time has since faded. But when a messy drunk driving incident lands him in jail, Paul finds he was specifically requested by Warden Hazen (James Cromwell), a duplicitous prison official well aware of Paul's athletic skills. Paul has been assigned the task of assembling a team of convicts, to square off in a big football game against the sadistic guards. With the help of fellow convict Caretaker, and an old legend named Nate Scarborough to coach, Crewe is ready for what promises to be a very interesting game. It's only the warden and the guards who have no idea who or what they're up against, with Paul the driving force behind the new team.