16 Most Notorious Prison Breaks That Ever Happened

4. Jack Shepherd (4 Times), 1724

John Dillinger Fake Gun
Wikipedia

Having been a carpenter, Shepherd turned to crime in 1723 when his love of whores and drink burned through his wages and his reputation. Astonishingly, in 1724 he was imprisoned five times and escaped four of them before the crown saw sense and executed him. By then he'd already become notorious.

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