In 1787, a man named Cuff (sometimes “Cophy” or “Cuffee”) Douglas sat down with a Quaker named Thomas Stapler to tell his story. Douglas was a free tailor, seventy years old, and he recounted how, after four decades of enslavement, he had worked to purchase his own freedom and that of his wife and three children, including his older son, also called Cuff. Stapler also noted that for the previous seven years, Douglas’ father-in-law, who was blind, had been living under his roof. Stapler would send the remarkable, though brief, biography to the London Abolition Society along with other similar accounts as proof that formerly-enslaved Black Americans were becoming pillars of society. That Douglas was chosen for a testimonial suggests that he was, in fact, one of the most prominent free Black Philadelphians of his time.