Douglass personifies the trickster in this instance, daring the other boys to do something that will be advantageous to him. This is similar to the tar baby tale, from the Uncle Remus stories, in which a rabbit that is stuck in tar, and therefore susceptible to the fox, suggests that the last thing he wants is to be thrown into a thorn bush. In fact, the rabbit feels at home in the thorns and uses them to escape, when the fox throws him into them.
MacKethan writes “Mastering letters enabled Douglass to write his ‘pass’ and to ‘pass’ into a world where he could no longer be named a slave” (64). Her use of antanaclasis here, or a homonymic pun, aligns MacKethan’s writing with the African American literary tradition, at least according to the criteria Henry Louis Gates, Jr. established in The Signifying Monkey. Hence, Lucinda MacKethan not only writes about the black literary tradition, she also participates in it as she writes about it.
Douglass’s reading lessons are supported by his observation of how the pieces of a ship are labelled. If we consider the role that sea vessels played with regard to bringing black people to captivity in the New World–the start of their slavery–it’s worth noting that the ships referenced here are relevant to the end of Douglass’s slavery, which is intertwined with his learning to read.