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Frederick Douglass was born into slavery sometime in 1817 or 1818. Like many enslaved people, he is unsure of his exact date of birth. Douglass is separated from his mother, Harriet Bailey, soon after he is born. His father is most likely their white master, Captain Anthony. Captain Anthony is the clerk of a rich man named Colonel Lloyd. Lloyd enslaves hundreds of men, women, and children, who call his large, central plantation the “Great House Farm.” Life on any of Lloyd’s plantations, like that on many Southern plantations, is brutal. Those enslaved are overworked and exhausted, receive little food, few articles of clothing, and no beds. Those who break rules—and even those who do not—are beaten or whipped, and sometimes even shot by the plantation overseers, the cruelest of which are Mr. Severe and Mr. Austin Gore.
Douglass’s life on this plantation is not as hard as that of most of the others. Being a child, he serves in the household instead of in the fields. At the age of seven, he is given to Captain Anthony’s son‑in‑law’s brother, Hugh Auld, who lives in Baltimore. In Baltimore, Douglass enjoys a relatively freer life. In general, city slave-owners are more conscious of appearing cruel or neglectful toward those they enslave in front of their non‑slaveowning neighbors.
Sophia Auld, Hugh’s wife, has never "owned" enslaved people before, and therefore she is surprisingly kind to Douglass at first. She even begins to teach Douglass to read, until her husband orders her to stop, saying that education makes enslaved people unmanageable. Eventually, Sophia succumbs to the mentality of slaveowning and loses her natural kindliness. Though Sophia and Hugh Auld become crueler toward him, Douglass still likes Baltimore and is able to teach himself to read with the help of local boys. As he learns to read and write, Douglass becomes conscious of the evils of slavery and of the existence of the abolitionist, or antislavery, movement. He resolves to escape to the North eventually.
After the deaths of Captain Anthony and his remaining heirs, Douglass is taken back to serve Thomas Auld, Captain Anthony’s son‑in‑law. Auld is a mean man made harsher by his false religious piety. Auld considers Douglass unmanageable, so Auld rents him for one year to Edward Covey, a man known for “breaking” enslaved people. Covey manages, in the first six months, to work and whip all the spirit out of Douglass. Douglass becomes a brutish man, no longer interested in reading or freedom, capable only of resting from his injuries and exhaustion. The turning point comes when Douglass resolves to fight back against Covey. The two men have a two‑hour fight, after which Covey never touches Douglass again.
His year with Covey over, Douglass is next rented to William Freeland for two years. Though Freeland is a milder, fairer man, Douglass’s will to escape is nonetheless renewed. At Freeland’s, Douglass begins educating his fellow enslaved people in a Sabbath school at the homes of free Black people. Despite the threat of punishment and violence they face, many enslaved people from neighboring farms come to Douglass and work diligently to learn. At Freeland’s, Douglass also forms a plan of escape with three fellow enslaved men with whom he is close. Someone betrays their plan to Freeland, however, and Douglass and the others are taken to jail. Thomas Auld then sends Douglass back to Baltimore with Hugh Auld, to learn the trade of ship caulking.
In Baltimore’s trade industry, Douglass runs up against strained race relations. White workers have been working alongside free Black workers, but the whites have begun to fear that the increasing numbers of free Black people will take their jobs. Though only an apprentice and still enslaved, Douglass encounters violent tactics of intimidation from his white coworkers and is forced to switch shipyards. In his new apprenticeship, Douglass quickly learns the trade of caulking and soon earns the highest wages possible, always turning them over to Hugh Auld.
Eventually, Douglass receives permission from Hugh Auld to hire out his extra time. He saves money bit by bit and eventually makes his escape to New York. Douglass refrains from describing the details of his escape in order to protect the safety of future slaves who may attempt the journey. In New York, Douglass fears recapture and changes his name from Bailey to Douglass. Soon after, he marries Anna Murray, a free woman he met while in Baltimore. They move north to Massachusetts, where Douglass becomes deeply engaged with the abolitionist movement as both a writer and an orator.