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.
