At the age of ten or eleven, Douglass's master dies and his property is left to be divided between his son and daughter. The slaves are valued along with the livestock, causing Douglass to develop a new hatred of slavery. He feels lucky when he is sent back to Baltimore to live with the family of Master Hugh.
He is then moved through a few more situations before he is sent to St. Michael's. His regret at not having attempted to run away is evident, but on his voyage he makes a mental note that he traveled in the North-Easterly direction and considers this information to be of extreme importance. For some time, he lives with Master Thomas Auld who is particularly cruel, even after attending a Methodist camp. He is pleased when he eventually is lent to Mr. Covey for a year, simply because he would be fed. Mr. Covey is known as a "negro-breaker", who breaks the will of slaves.