Frederick Douglass was born Frederick Bailey in February 1818, a slave belonging to Aaron Anthony, an overseer employed by Colonel Edward Lloyd in Talbot County, Maryland, on the eastern shore of the Chesapeake Bay. The boy scarcely knew his mother, who was expected back at work on Anthony's own farm soon after the birth, and he was raised by his grandmother in a cabin in the backwoods where her husband, a free man, earned a precarious living as a woodcutter. At the age of six Frederick was considered ready to take up duties at the big house of Lloyd's Wye Plantation, twelve miles distant, rejoining his three older siblings. Here he first witnessed the cruelties of overseers, which haunted him for the rest of his life. And then, two years later, he was wrenched away once more. Anthony's son-in-law, Thomas Auld, sent the young boy to live with his brother Hugh and his wife Sophia in Baltimore, the second largest city in the United States at the time, and the best part of a day's sail from the plantation.

There was no question of the boy receiving any formal education, but Sophia began to teach him how to read, before her husband stopped her, declaring that it was against the law, and even she now became cold towards him. But Frederick was tenacious and thereafter he sought every opportunity to continue his education in secret: he got hold of a copy of the Columbian Orator, a popular textbook with extracts from famous speeches, copying letters and enlisting the (sometimes unwitting) help of white boys he encountered in the shipyards.

When he was fifteen, Thomas Auld, now his owner, called him back to Talbot County and hired him out to various farms. This would have been Frederick's first real taste of demanding manual labour in the open air, and hard to take after the relatively light duties he had enjoyed in Baltimore. Auld, determined to take him down a peg or two, probably relished his discomfort. Indeed, after discovering that the enterprising youth had set up a clandestine Sabbath school, he resolved to teach him a lesson. In January 1834 he hired him out for a year to Edward Covey, a man with a reputation for disciplining hard-to-manage slaves.