These five ‘gangsta’ slaves made some of the most daring escapes we’ll never forget

Frederick Douglass

Then known by his birth name Frederick Augustus Washington Bailey, Douglass had attempted to escape over the past two years before his success. After meeting a free Black woman, Anna Murray, and falling for her, Douglass hatched his plan of attack with Murray’s help when he was just 20 years of age.

On September 3, 1838, Douglass hopped aboard a railroad train heading north disguised as a free Black sailor. The ruse was made possible by Douglass’ knowledge of the sea by way of his working on the Baltimore waterfront. He was able to obtain sailor’s papers from a free man as part of his ruse and donned an outfit befitting of the role he played. By miracle and fate, the White train conductor did not discover Douglass’ impersonation and he rode the train through the slave states of Maryland and Delaware, still not outside the confines of danger and doubt. When he reached the town of Havre de Grace in Maryland, which at the time was near the Pennsylvania border, he crossed the Susquehanna River by ferry. The stressful journey finally ended when Douglass reached the safe house of abolitionist David Ruggles in New York City.