Douglas spent a year (1833) with Covey, during which he was frequently and brutally whipped. Having spent considerable time in the city, Douglass was not familiar with farm instruments and techniques. Because of this unfamiliarity, he made mistakes and was continually punished. Covey pushed his slaves to the limit, making them work long hours, and he constantly spied on them to make sure they did the work. Despite his professed religious piety, Covey saw profit in breeding slaves, so he bought a female slave and hired a married man to have sex with her for a year. Douglass confesses that witnessing this inhuman tyranny may have been the lowest point in his life for he contemplated killing Covey and ending his own life. Because Covey's farm was located on Chesapeake Bay, Douglass often saw ships from all around the world. The sight of their billowing white sails continually renewed his hope for an eventual escape.
One hot day in August, Douglass collapsed from fatigue, an event which led to matters that changed his life. Covey came by, kicked him, and gave him a beating. Although Douglass was bleeding profusely, he managed to escape and walked seven miles to St. Michael's, to ask Master Thomas for help. Although Thomas didn't believe Douglass' story and sent him back to Covey in the morning, he did allow him to stay for the night. On reaching Covey's farm, Douglass found himself the object of another beating. This time, however, Douglass ran into the cornfields and Covey couldn't find him.
Eventually, Douglass encountered Sandy Jenkins, a fellow slave who believed in the supernatural powers of certain plants. Sandy advised him to carry a certain root on his right side, an act which would make it impossible for any white man to harm him. Sandy believed that his own root had always saved him. To humor Sandy rather than argue with him, Douglass followed his instructions. To Douglass' surprise, when he returned to Covey's farm, Covey spoke kindly to him. A few days later, however, Covey pounced on him. This time, Douglass decided to physically resist. In the ensuing fight, Douglass gained the upper hand, and, after nearly two hours of wrestling and struggling, Covey finally gave up. Douglass recalls:
"Covey at length let me go, puffing and blowing at a great rate, saying that if I had not resisted, he would not have whipped me half so much. The truth was, that he had not whipped me at all."
Douglass thinks that because Covey enjoyed a widespread reputation for being the region's best slave breaker, it provided him with plenty of free labor, and he didn't want to punish Douglass any further because doing so would be an admission of his having lost a physical fight. For the rest of Douglass' stay, Covey didn't touch him again. Douglass recalls: "This battle with Mr. Covey was the turning-point in my career as a slave. It rekindled the few expiring embers of freedom, and revived within me a sense of my own manhood. It recalled the departed self-confidence, and inspired me again with a determination to be free."
Douglass then discusses why slaveholders allowed slaves to celebrate holidays. If it were not for these days of rest, Douglass reasons, that there would be a multitude of slave insurrections. Holidays, he says, are opportunities for slave owners to encourage slaves to get drunk, and keeping slaves drunk is one way of keeping them servile.
Douglass' tenure with Covey ended after a year, and he was hired out to William Freeland in January 1834. Douglass calls Freeland "the best master I ever had, till I became my own master." Freeland never hit Douglass, but, more important, he didn't profess religiosity. Douglass tells the reader that religious slave owners are all unparalleled hypocrites, vicious and perverse.
Douglass soon grew attached to other slaves with whom he worked, and together they celebrated the Sabbath. Douglass became the Sabbath school instructor to his fellow slaves, a task he enjoyed greatly.
In 1835, Douglass began to think seriously about escaping. Together with several other slaves, he planned to steal a canoe and row up Chesapeake Bay. He even forged notes stating that they had permission from their owners to travel to Baltimore. This escape attempt failed, however, before it began because another slave betrayed them. The group was arrested, and, to Douglass' surprise, Thomas Auld came to the jail and arranged for Douglass' release. Douglass, however, was considered the ringleader, so there was a general dislike of him in the community. Auld eventually sent him to live with his brother Hugh because he feared that someone might kill him. In turn, Hugh loaned Douglass to William Gardner, a ship builder.
For several months, Douglass was at "the beck and call of about seventy-five men," continually running errands for them. He might have stayed longer had it not been for a fight he had with his fellow white workers. The white carpenters were worried that free black men and slaves might become so proficient that they might eventually take their jobs away. One day, Douglass' fellow white apprentices started heckling and striking him. Because Douglass had promised himself after the Covey incident that he would fight back if physically mistreated, he struck back, and the ensuing fight nearly turned into a mob scene. Douglass was badly beaten and feared being lynched. In the end, however, he managed to escape.
Returning to Hugh Auld, he found his master and mistress surprisingly very kind to him. After taking care of his wounds, Auld took him down to Gardner to lodge a complaint. None of the white workers would testify on his behalf, though, and the words of black workers meant nothing.
Master Hugh didn't let him work with Gardner again; instead, he sent Douglass to work in the shipyard where he was foreman. Douglass took up the task of caulking (waterproofing boats) and soon became a skilled worker. In time, he started earning wages equal to the most skilled caulkers. All of his salary went to Hugh Auld, though, and this injustice made him more determined than ever to escape.
