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

Anna Maria Weems

She is remembered as the woman who escaped slavery around the White House dressed as a man. Born into slavery about 1840 in Maryland, Weems escaped through the Underground Railroad, despite how risky that was.

J. Bigelow, a lawyer from Washington, D.C., who had earlier helped Weems’ family purchase their freedom, came out with a plan to help her escape to freedom. On September 23, 1855, Weems, then 15, escaped the home of her slaveowners in Montgomery County and made her way to Bigelow’s residence, one of the safe houses used as hiding places along the lines of the Underground Railroad.

Due to a $500 reward for anyone who could bring her back, Bigelow hatched another plan. Weems was to dress up as a boy named “Joe Wright” in driver’s uniform, including a jacket, bow tie, pants, and cap. In late November, when her escape was no longer in the headlines, Dr. Ellwood Harvey, the Bigelow family physician, drove his carriage and parked it along the side of the road in front of the White House. As part of the plan, he climbed into the passenger compartment and waited for “Joe Wright” to arrive, who was escorted by Bigelow. The plan was to make people believe that Dr. Harvey had just completed some work in the White House and was now being escorted by his coachman.

Weems, now dressed as “Joe Wright”, successfully drove the carriage out of Washington and that began her journey to freedom.