Willie Sutton's criminal activities began when he was young. He robbed about 100 banks from the late 1920s through the heydays of the Mafia era during the Great Depression to his final arrest in 1952 - with several prison terms in between; he was also a master at breaking out of prisons.

An accomplished bank robber, he usually carried a pistol or a Thompson submachine gun. "You can't rob a bank on charm and personality," he once observed.

In an interview to the Reader's Digest published shortly before his death 2 November 1980, Sutton was asked if the guns that he used in robberies were loaded. He responded that he never carried a loaded gun because somebody might get hurt; Sutton is said to have taken great pride in never using the guns that he carried.  

A gentleman to the core, Sutton allegedly also never robbed a bank if a woman in the premises screamed or a baby cried.

According to the FBI's dosier on him, Sutton had the reputation of a gentleman; in fact, people present at his robberies stated he was quite polite. One victim said witnessing one of Sutton's robberies was like being at the movies, except the usher had a gun.

It is estimated that Willie Sutton stole perhaps $2 million in his career, and spent more than half his adult life in prison, dispening mounds of legal advice to any convict intelligent enough to listen.