It was the curious fate of Douglass to pass through almost every phase of slavery, as though to prepare him the more thoroughly for his future career. Shortly after he went to Baltimore, his master, Captain Anthony, died intestate, and his property was divided between his two children. Douglass, with the other slaves, was part of the personal estate, and was sent for to be appraised and disposed of in the division. He fell to the share of Mrs. Lucretia Auld, his masters daughter, who sent him back to Baltimore, where, after a month's absence, he resumed his life in the household of Mrs. Hugh Auld, the sister-in-law of his legal mistress. Owing to a family misunderstanding, he was taken, in March, 1833, from Baltimore back to St. Michaels.

His mistress, Lucretia Auld, had died in the mean time; and the new household in which he found himself, with Thomas Auld and his second wife, Rowena, at its head, was distinctly less favorable to the slave boy's comfort than the home where he had lived in Baltimore. Here he saw hardships of the life in bondage that had been less apparent in a large city. It is to be feared that Douglass was not the ideal slave, governed by the meek and lowly spirit of Uncle Tom. He seems, by his own showing, to have manifested but little appreciation of the wise oversight, the thoughtful care, and the freedom from responsibility with which slavery claimed to hedge round its victims, and he was inclined to spurn the rod rather than to kiss it. A tendency to insubordination, due partly to the freer life he had led in Baltimore, got him into disfavor with a master easily displeased; and, not proving sufficiently amenable to the discipline of the home plantation, he was sent to a certain celebrated negro-breaker by the name of Edward Covey, one of the poorer whites who, as overseers and slave-catchers, and in similar unsavory capacities, earned a living as parasites on the system of slavery. Douglass spent a year under Coveys ministrations, and his life there may be summed up in his own words: "I had neither sufficient time in which to eat nor to sleep, except on Sundays. The overwork and the brutal chastisements of which I was the victim, combined with that ever-gnawing and soul-destroying thought, 'I am a slave,—a slave for life,' rendered me a living embodiment of mental and physical wretchedness."

But even all this did not entirely crush the indomitable spirit of a man destined to achieve his own freedom and thereafter to help win freedom for a race. In August, 1834, after a particularly atrocious beating, which left him wounded and weak from loss of blood, Douglass escaped the vigilance of the slave-breaker and made his way back to his own master to seek protection. The master, who would have lost his slave's wages for a year if he had broken the contract with Covey before the year's end, sent Douglass back to his taskmaster. Anticipating the most direful consequences, Douglass made the desperate resolution to resist any further punishment at Covey's hands. After a fight of two hours Covey gave up his attempt to whip Frederick, and thenceforth laid hands on him no more. That Covey did not invoke the law, which made death the punishment of the slave who resisted his master, was probably due to shame at having been worsted by a negro boy, or to the prudent consideration that there was no profit to be derived from a dead negro. Strength of character, re-enforced by strength of muscle, thus won a victory over brute force that secured for Douglass comparative immunity from abuse during the remaining months of his year's service with Covey.

The next year, 1835, Douglass was hired out to a Mr. William Freeland, who lived near St. Michael's, a gentleman who did not forget justice or humanity, so far as they were consistent with slavery, even in dealing with bond-servants. Here Douglass led a comparatively comfortable life. He had enough to eat, was not overworked, and found the time to conduct a surreptitious Sunday-school, where he tried to help others by teaching his fellow-slaves to read the Bible.