Stupidity: Andy meets Tommy Williams who names another convict who described the scene of the murder of Andy's wife and her lover in sufficient detail to convince anyone that something was wrong with Andy's conviction. Andy then goes to the Warden, a man he knows to be utterly corrupt, a man who will suffer a huge loss if he is acquitted. Andy is an intelligent man - why would he do something as stupid as that? Why doesn't he write to his lawyer? This is a matter for an appeal court, not the Warden.
The Shawshank Redemption (1994)
1 stupidity
Directed by: Frank Darabont
Starring: Morgan Freeman, Clancy Brown, Tim Robbins, William Sadler, Bob Gunton, Gil Bellows
Factual error: When Red is sitting under the oak tree in 1967 and pulls the money out of the envelope, the top bill is signed by Nicholas F. Brady, who was Secretary of the Treasury September 1988 - January 1993. It's less about reading the handwriting as noting the different appearance of different signatures from different eras. (02:14:40)
Andy Dufresne: Get busy living, or get busy dying.
Trivia: There are many references to the number 237 in the movie. For instance, this is the number of Red's cell, and these digits are on Andy's prison I.D. This number makes appearances throughout Steven King stories, the most famous one being the room where the murders take place in "The Shining".
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Chosen answer: In a nutshell, tax evasion. He's running the prison like a company doing building work with, as its described by the builder in the movie, a pool of slave labour to allow him undercut other contractors. He is skimming profit for his own pockets, along with taking bribes, etc. that Andy's creative book keeping is hiding from the IRS.