Who did Frederick Douglass miss the most when he left Baltimore?
When Frederick left Baltimore, it was the "little Baltimore boys" that he missed the most (Chapter VIII).
Frederick's mistress, Sophia Auld, had begun to teach Frederick to read, but was soon caught and forbidden to do so by her husband. It wasn't long before Sophia herself was corrupted by the influence of the institution of slavery; not only did she cease teaching Frederick but she became "even more violent in her opposition" to allowing slaves to achieve literacy than her husband himself. Sophia had instilled a hunger for learning within young Frederick, however, which was not to be denied. He began making friends with "all the little white boys whom (he) met on the street", giving them bits of bread in exchange for lessons in reading. Frederick would surreptitiously carry a book with him whenever he was sent on errands, working quickly so that he would have time to sneak in a lesson here and there. As bread was more plentiful in the Auld household than in the homes of many of the poor white children in the neighborhood, the exchange was beneficial for all involved (Chapter 7). Frederick developed a stong attachment to the little Baltimore urchins, and "the thought of leaving them was painful indeed" (Chapter 8).