5.9k Share this

Sheppard’s crimes ramped up, but he was an amateur compared to some of his contemporaries, and eventually wound up in the clutches of law enforcement (via Historic UK). His first arrest landed him in prison on a pick-pocketing charge. According to Britannica, he put together a successful escape attempt in April 1724 by breaking a chair and using it to create a hole in the ceiling of his jail cell. Then he climbed onto the roof and escaped by blending in with a crowd of people, per the BBC.

However, Sheppard had a habit of returning to one of his favorite watering holes, the Black Lion, after his escapes, which made him pretty easy to track down, and was usually pretty drunk by the time anyone came looking for him.

His second and third escapes were both accomplished the same way: by having visitors bring him tools which he used to free himself from his cell. The second time he was imprisoned, he was allowed to share a cell with Edgewater Bess, and he used her clothes and his to make a rope that he used to complete his escape. On the third escape, once out of his cell, he left the prison disguised as a woman. Sheppard’s fourth escape was done by climbing out onto the roof of the prison, much like he did in his first escape, only this time he accessed it by climbing up a chimney.

Source: This post first appeared on

5.9k Share this
You May Also Like

Trial of Clinton lawyer Michael Sussmann begins

The first trial to emerge from Special Counsel John Durham’s probe finally…

Ted Cruz Wins in Campaign Finance Case at Supreme Court

Senator Ted Cruz (R-Texas) The Supreme Court’s conservative majority ruled 6-3 in…

Heartbroken Parents Visit Scene Where 11-Year-Old Daughter Shot Dead by ‘Stray’ Bullet – Crime Online

An 11-year-old girl was shot and killed Monday by a gunman on…

Former Hospital Employee Charged With Murder 20 Years After Spate Of Deaths

Franco’s granddaughter, Aprille Franco hopes investigators get to the bottom of the…

[Update] Convicted Sex Offender Raymond Moody Admits to Killing Brittanee Drexel, Leads Police to Remains: Cops – Crime Online

A convicted South Carolina sex offender reportedly admitted to the murder of…

Thomas Lane Admits to Manslaughter of George Floyd

Thomas Lane Former Minneapolis Police Officer Thomas Kiernan Lane pleaded guilty on…

Vicky and Casey White Paid Sex Offender $100 to Reserve Motel Room They Hid in Amid Manhunt: Police – Crime Online

Alabama corrections officer Vicky White allegedly paid a homeless sex offender $100…

Florida Woman Admits Killing Elderly Man, Burying Him in Backyard – Crime Online

A Florida woman was charged this week with killing an elderly man…