The epic battle leaves Covey chastened and henceforth “gentle as a lamb” (117). Frederick, meanwhile, sees his reputation growing. His fellow Eastern Shore slaves know that he can read and write. Now they know he will fight, too. Unfortunately, Frederick knows he is unusual and that the slave system makes it nearly impossible for slaves to develop habits that will make them both yearn for freedom and fight for it. During the week between Christmas and New Year’s Day, for instance, slaveholders encourage slaves to spend their holiday free time drinking and playing games. Indeed, masters might view anything less than mindless debauchery as a sign of impudent aspirations toward self-improvement.

On January 1, 1835, one year after arriving at Covey’s, Frederick leaves for his next assignment at the farm of William Freeland, whom he finds to be a much better man than Covey. Though his situation is “every way improved,” Frederick remains “restless and discontented” (121). At Freeland’s, Frederick meets fellow slaves Henry and John Harris, Handy Caldwell, and Sandy Jenkins, the same Sandy who gave him food and shelter while he was hiding in the woods from Covey. With these men and a few dozen others as both friends and students, Frederick begins a Sunday school.