On January 1st, 1833, Douglass leaves Master Thomas’s to work as a field hand for Mr. Covey. Douglass’s city upbringing makes him unfit for this labor. In the first few days, Covey sends Douglass with a team of oxen into the forest to retrieve some wood. Douglass does not know how to manage the oxen, and they startle and upset the cart. Douglass narrowly escapes injury. He is stranded in the middle of the woods with a damaged cart and a team of oxen tangled in their own reins. Douglass manages to re-yoke the oxen and sets off again, but they quickly become frightened for a second time, and nearly run Douglass into a gate. After Douglass reports his troubles to Covey, Covey whips him savagely.
Douglass’s experience trying to manage the team of oxen demonstrates the unfair expectations masters have of their slaves. Covey can’t be bothered to teach Douglass to handle the oxen, and Douglass assumes a task at great physical risk—but nevertheless, Covey blames Douglass when things go wrong, and whips him for the accident.
During Douglass’s first six months living with Covey, he was whipped roughly once a week. Covey works his slaves from before dawn till after dusk, and while he gives them enough food to eat, he does not give them enough time to eat it. To ensure productivity, Covey labors alongside his slaves, and Covey will often sneak up on his slaves in order to make sure they work even when unsupervised. Covey often uses elaborate ruses to trick the slaves into thinking he has disappeared, only to watch his slaves from a hidden vantage point. This forces the slaves to work constantly, from fear of constant surveillance.
Covey is Douglass’s most sinister master. Not only does he make extraordinary physical demands of his slaves, he also uses trickery and deceit to erode their mental strength. Life on Covey’s farm consists of nothing but constant work and constant paranoia.
Covey’s sinister powers of deception also extend into his religious practice. He prays frequently, but only in ways that do not give the slaves a break from fieldwork. Covey often sings hymns with his family, but is not a strong reader, and Douglass is usually required to read the hymns. However, Douglass often refuses, which unsettles Covey, and forces him to read haltingly to show his independence from the slave.
Covey is the worst sort of religious hypocrite—he feigns intense Christian faith, but only when it is advantageous for him to do so. Douglass’s refusal to read is a small act of rebellion that affirms that Covey hasn’t broken him completely.
Covey is a poor man, who can only afford to own one slave (he “rents” the others from different slave-owners). This slave was a twenty-year-old woman named Caroline, whom Covey bought as a “breeder.” He compels another man to sleep with Caroline nightly, and after some time, Caroline gives birth to a pair of twins.
“Breeding” slaves is one of the most morally outrageous practices of slavery, and it further refutes Covey’s professed commitment to Christianity.
Douglass is broken by his six months with Covey. He is forced to work in every weather condition, no matter how hot or cold. The constant toil erodes Douglass’s hope and destroys his interest in intellectual pursuits. He spends Sundays—his only leisure time—in a dream-like stupor, unable to think clearly. He entertains the idea of killing himself or Mr. Covey, but cannot follow through out of a combination of hope and fear.
Under Covey, Douglass reaches his lowest point. His enslavement is so total that he can no longer use the one thing he retains full control of: his mind. The stupor Covey’s practices induce in Douglass illustrates the dulling of slaves’ minds that allows slavery to continue. Slave owners treat slaves this way on purpose—only with such inhumane treatment can they beat their slaves down enough to keep slaves down.
Covey’s house is on the Chesapeake Bay, and Douglass’s regular sight of the far-ranging ships in the harbor makes him fearful and sad about his wretched condition. The sight of the ships inspires him to attempt to run away and seek freedom.
To Douglass, the ships in the Chesapeake symbolize freedom of movement and control over one’s destiny.
While fanning wheat for Covey in August of 1833, Douglass collapses from heat exhaustion and is unable to continue working. Covey hits Douglass and demands he continue working. Douglass rises and resumes work, but he vows to complain to Master Thomas about Covey’s treatment. After work, a disoriented Douglass ignores Covey’s orders to stay put and stumbles seven miles to Thomas’s house. Thomas ignores Douglass’s complaints, and says that Covey is a good man who poses no danger of killing Douglass.
Douglass’s choice to appeal to Thomas shows how desperate he has become. The trip to Thomas’s surely required a good deal of effort from the exhausted slave, and, besides, Douglass already knew that Thomas was an uncompassionate master.
Douglass spends the night in St. Michael’s, and returns to Covey’s the next day. He sees Covey running out to whip him and successfully hides in the cornfields. Douglass spends the day in the woods, and meets a slave named Sandy Jenkins, who is on his way to the house where his free wife lives. Jenkins takes Douglass home with him. There, he tells Douglass to return to Covey, but to always carry with him a special root on his right side. This root, Jenkins says, will prevent a master from hitting any slave that carries it. Douglass is skeptical, but agrees to follow Sandy’s insistent advice.
Sandy in several ways represents a commonly held negative stereotype of the slave. He is superstitious—he believes in the powers of a mystical root—and he is very deferential to his master, which shows in his recommendation to Douglass that he return to Covey.
The next day, Sunday, Douglass returns to Covey’s carrying the root on his right side. On his way back, he passes Covey, who is headed to church. Covey speaks to Douglass kindly, and Douglass begins to believe in the root’s powers. The next morning, Douglass is given an early chore, and as he works, Covey catches Douglass off guard and ties his legs up. Douglass falls down, but resolves to fight Covey, and seizes his master by the throat. Another farmhand, Hughes, comes to help Covey, but Douglass incapacitates him with a kick to the ribs. The two fight for two more hours, and Covey finally gives up without having whipped Douglass.
Regardless of the actual merit of Sandy’s superstitious beliefs about the root, Douglass’s rebelliousness and self-confidence has been restored. By responding in kind to Covey’s violence, Douglass intimidates his master and keeps Covey’s abuse in check.
The fight with Covey renews Douglass’s self-confidence and his desire to be free, and he experiences a satisfaction that could only be understood by someone who has himself repelled slavery. Though Douglass remains a slave for four years after the fight, he is never again whipped.
This event marks a turning point in Douglass’s life, as he now understands the value of standing up to protect himself.
Douglass is at first surprised that Covey doesn’t have him whipped by a constable. Douglass theorizes that Covey doesn’t want to lose his reputation as a slave-breaker, and having Douglass whipped in public would discredit Covey.
Douglass’s defiance exploits Covey’s insecurities. While Covey holds more power than Douglass, he is clearly a weaker man both physically and spiritually, and his reputation as a slave breaker makes him vulnerable to those slaves he can't break. He has to keep them from revealing his failure, and can only do that by giving in to them.
Douglass’s year of service to Mr. Covey ends on Christmas Day of 1833. Slaves are given the days between Christmas and New Years off as holidays. Some spend this time preparing industriously for the coming season, but most simply revel. Douglass sees these holidays not as an illustration of the slaveholders’ benevolence, but as a calculated attempt to prevent insurrection. Slaveholders encourage the slaves to drink heavily and sicken themselves, so that the slaves will believe they cannot live independently. Part of the inhumane fraud of slavery, Douglass says, is to disgust the slave with his freedom.
The debauchery of the holidays illustrates the slaveholders’ despicable methods of ensuring slaves’ complacence. By keeping slaves ignorant of what true freedom is like, the slaveholders convince them that they do not deserve the privilege. The malicious trickery of the holiday season is a strong example of the way slave owners perpetuate slavery through ignorance and deception.
On January 1st, 1834, Douglass is sent to live with William Freeland, who lives near St. Michael’s. Freeland is a more honorable man than Covey, and does not deceive his slaves. Douglass is also relieved that Freeland does not try to use religion to justify owning slaves, because Douglass has found religious slaveholders to be the most cowardly and cruel. For example, Mr. Weeden and Mr. Hopkins, two ministers who live near Mr. Freeland, regularly whip their slaves for no reason other than to assert their own authority.
Freeland is, to Douglass, a less objectionable slaveholder because he does not use religion to engineer a moral justification for his ownership. Ironically, his de-emphasis of religion makes him a more humane master.
Mr. Freeland treats Douglass more fairly than Covey did, giving his slaves both enough to eat and enough time to eat. Freeland himself owns only two slaves, Henry and John Harris. Douglass is a hired hand, along with Sandy Jenkins and Handy Caldwell. Douglass instills in his fellow slaves the desire to learn to read, and he spends his Sundays teaching them. The school expands—Douglass remembers teaching over 40 people at one point. Douglass is touched by the risks the slaves take in order to educate themselves, and looks back on his teaching days with great pleasure and pride.
Douglass’s belief that education can bring empowerment—and his dedication to his fellow slaves—is made clear in his commitment to teaching the reading class. It also shows how a slave who can read is a threat to slavery, because that slave can pass both knowledge and the skill onto other slaves, who can then pass on their knowledge and the skill, etc., breaking down the ignorance that keeps slaves from thinking critically about their enslavement.
Douglass passes a relatively easy year with Mr. Freeland. He attributes some of his comfort to the love that he shares with his fellow slaves. In 1835, at the end of his first year, Douglass is taken again for a second year with Freeland. Douglass decides that he would rather live “upon free land” than “with Freeland,” and resolves that 1835 will not come and go without an attempt to escape.
The human connection Douglass experiences with his fellow slaves makes his experience at Freeland’s easier to endure. However, Douglass is not content with his relative comfort, and will finally make good on his promises to attempt an escape.
It is important to Douglass to convince his fellow slaves to escape with him. They meet frequently to plan their flight, and are intimidated by the dismal odds they face. Finally, they become determined to run away—to Douglass, this is more impressive than Patrick Henry’s trademark cry of “give me liberty or give me death,” as the slaves were faced with the prospect of dubious liberty or certain death.
Again, Douglass’s compassionate concern for his fellow slaves compels him to include them in his escape plans, likely at greater risk to himself. Symbolically, it’s noteworthy that Douglass’s decision to seek liberty is seen as a more profound choice than the founding fathers’.
Douglass’s escape plan involves his group of slaves paddling a canoe up the Chesapeake to reach the north. The group of escapees consists of Henry Harris, John Harris, Henry Bailey, and Charles Roberts. Sandy Jenkins was initially going to come, but backed out. To give their escape some plausibility, Douglass forges written travel passes from a master.
Douglass’s ability to read and write gives the escaping slaves a strategic advantage. Because their intelligence is constantly underestimated, nobody will guess that they could have forged their own passes.
On the day the slaves had planned to flee, Douglass goes to work as usual. However, he is overcome with an inexplicable feeling of betrayal. Then, without warning, Douglass and his co-conspirators are tied up and brought to jail in Easton. Douglass manages to destroy the pass he had written, and he and his co-conspirators agree to deny their plot.
Sandy’s last-minute choice to back out of the escape suggests that he may have been the one who betrayed his fellow slaves.
In jail, slave traders appraise and demean the imprisoned slaves. After some time in jail, all the slaves except Douglass are taken home; this separation pains Douglass dearly. Douglass believes that he will be the only one sold, because he was the ringleader of the escape plan.
Notably, what hurts Douglass most about his time in jail is his separation from his fellow slaves.
While languishing in jail, Douglass abandons hope. His master, Thomas Auld, announces plans to send him to Alabama. However, Thomas decides instead to send Douglass back to Baltimore to live with Hugh Auld.
Once again, it seems as though providence has intervened to improve Douglass’s luck.
When Douglass arrives in Baltimore, he is apprenticed to a ship-builder named William Gardner, who will teach him how to caulk ships. However, because the shipyard is scrambling to meet a tight deadline, Douglass is overwhelmed with simple errands and cannot learn any new skills. After eight months working in the shipyard, Douglass is assaulted by a group of four white apprentices. The white carpenters have become disgruntled working with blacks, because they fear that the blacks will take their jobs. Douglass tries to fight back, but is badly beaten. Despite there being many witnesses to Douglass’s assault, nobody comes to his aid.
When he is assaulted by the white carpenters, Douglass is targeted simply because he is an unwilling part of an unfair system. Douglass doesn’t represent any meaningful threat to the carpenters’ jobs, and, more importantly, it isn’t even his choice to work. Nevertheless, racist insecurities prevail over logic, and the blameless Douglass is beat up.
Douglass returns to Master Hugh that day, and Sophia cares for his wounds. Hugh is outraged at the violence done to Douglass, and speaks to a lawyer. The lawyer informs Hugh that he has no legal recourse, unless a witness will step forward on Douglass’s behalf. No blacks can testify, and no whites—even those who sympathize with Douglass—will testify for Douglass and against a fellow white man.
Douglass’s beating exemplifies the injustice that slaves face. He is beat in front of numerous witnesses, but individual and institutional racism prevents his case from being handled fairly by the law.
With no chance for redress, Hugh nurses Douglass back to health in his home, and then apprentices the slave to another caulker, Mr. Walter Price. Douglass learns the trade, and is soon able to earn wages of six or seven dollars per week. Douglass now routinely earns money, but is compelled to turn it all over to Master Hugh at the end of each week. This “piracy” of his pay makes Douglass resent slavery still more: he realizes that every improvement in his condition only makes him desire freedom further, because slavery depends on keeping the enslaved in moral and intellectual darkness, so that slaves cannot see the inconsistencies of slavery.
Douglass is beginning to develop more and more of the characteristics that freemen have. He has learned a trade and cultivated his intellect. This worldliness only makes Douglass more aware of the unfairness of his situation—he has the same skills as others who can make a living for themselves. But Douglass's money goes to his masters. The better equipped he is to recognize the hypocrisy of slavery, the more acutely Douglass recognizes it.