In 1935, a con man was arrested for selling his victims a “currency copier”, purportedly capable of reproducing $100 bills. The day before his trial, he fashioned sheets into a rope and slipped out the window, pretending to be a window washer as he shimmied down the building.
Steven Jay Russell impersonated a prison guard to simply walk out of prison. Upon recapture Russell lowered and paid his bail by pretending to be a judge, escaped his next capture by impersonating a doctor, and did so AGAIN by faking his death, eventually landing him a 144yr sentence.
Steven Russell escaped from prison by using laxatives to fake the symptoms of AIDS. He then called the prison, posing as a doctor, asking for prisoners interested in an experimental treatment, and volunteered. Once out of Texas, he sent death certificates to the prison stating he had died.