In November of 1815, an enslaved woman known only as Anna jumped out of a third floor window in Washington DC in what was assumed to be a suicide attempt. Presumed dead, abolitionists used her story to expose the harsh realities of slavery and advocate for better treatment of slaves. In 2015, the Oh Say Can You See research project uncovered an 1828 petition for freedom from an Ann Williams for herself and three children. This woman was the same “Anna” who had leapt from the window, still alive but severely injured from her fall, a contrast to the widely held belief that she had died in the fall. In 1832, a jury ruled in her favor, granting Ann and her three children freedom from master George Williams. Ann and her children went on to live free in Washington, subsisting on the weekly $1.50 that Ann’s still enslaved husband was able to provide for his family. This inquiry and the compelling question seeks to address the autonomy that enslaved African Americans had, and the question of what freedom meant to Anna.