“A child might play in his arms, or dance on his shoulders.”

In addition to being a moral person, Madison is gentle and kind. This quote develops his characterization by illustrating how he would handle children, including his own, with care and concern. The art of dance connects to other the arts referenced in the story, such as drawing and photography; it is a human pursuit that Black and white people share and a way to immortalize a moment.

“Madison (for that was the name of our hero).”

Madison’s name is revealed after Listwell and the reader hear his lamentations and prayers. Douglass’s use of the inclusive pronoun “our” is a way to appeal to the readers and persuade them to become abolitionists. Madison becomes a hero not only in the story but also to the reader.

“The hope of freedom seemed to sweeten, for a season, the bitter cup of slavery.”

This is a metaphor that compares freedom with sweetening a beverage in a cup, such as tea. The Boston Tea Party was part of the American Revolution, which Douglass frequently references. Freedom is sweet and pleasing to drink, while the violent institution of enslavement is bitter and hard to swallow.

“With true canine instinct, Monte quickly discovered that a friend, not an enemy of the family, was coming to the house, and instead of rushing to repel the supposed intruder, he was now at the door, whimpering and dancing for the admission of himself and his newly made friend.”

This quote develops the symbolism of animals. Listwell’s dog, Monte, is happy to see Madison. Listwell teaches Monte that Madison is a friend, rather than seeing him as an “intruder.” This can be contrasted with the “bloodhounds” that search for Madison after his escape. They are trained to treat him as dangerous.

“Here were hunger, cold, thirst, disappointment, and chagrin, confronted only by the dim hope of liberty.”

This is just one example of the repetition of the word “liberty,” developing the theme of The Pursuit of Liberty. Madison endures the trials of escaping enslavement because they will lead to liberty and freedom. Douglass emphasizes the significance of these trials through his use of a long list, contrasted with his singular “dim hope”: liberty. This underscores the material challenges that Madison must overcome to achieve freedom.

“I dreaded more these human voices than I should have done those of wild beasts.”

This is another example of the symbolism of animals. Madison is more comfortable with the “wild beasts” that roam free in the woods than with white people. Animals will only harm him if he upsets them or they are hungry. White people harm enslaved people because they believe that enslaved people are property, not humans.

“When he arose from his knees, like another Zacheus, I came down from the tree.”

This is a Biblical allusion from Luke 19:1-10. Zacheus is a tax collector who climbs a tree to see Jesus. After Jesus asks him to come down, Zacheus vows to give away most of his money. Madison compares himself to Zacheus when he explains how he came down from hiding in a tree to talk to another enslaved person.

“I caught a glimpse of the Great Bear (which ever points the way to my beloved star).”

The north star, Polaris, was significant to many enslaved people, as it guided them to freedom when leaving the American South. Abolitionists lived in the Northern states, and Canada (as a British colony) regarded chattel enslavement as illegal. Locating the Great Bear constellation is a way to locate the north star.

“For if it cost my farm, I shall see you safely out of the States, and on your way to a land of liberty.”

Here, Listwell describes his dedication to the cause of abolition. His willingness to endure economic hardship to help a freedom seeker supports the theme of Presenting Models of White Allyship. Douglass presents Listwell to white readers at the time of his writing as a strong example to imitate.

“He had done something ‘to deliver the spoiled out of the hands of the spoiler,’ he had given bread to the hungry, and clothes to the naked; he had befriended a man to whom the laws of his country forbade all friendship,—and in proportion to the odds against his righteous deed, was the delightful satisfaction that gladdened his heart.”

This passage further develops the theme of presenting models of white allyship. Listwell experiences pleasure in assisting Madison because his act is morally correct but illegal. Douglass appeals to not only pathos for the pain of enslaved people but also pathos for the joy of participating in abolition. Douglass does so to convince his readers to follow Listwell’s example.

“For, hating slavery as he did, and regarding it to be the immediate duty of every man to cry out against it, ‘without compromise and without concealment,’ it was hard for him to admit to himself the possible of circumstances wherein a man might, properly, hold his tongue on the subject […] he concluded […] that it was wiser to trust the mercy of God for his soul, than the humanity of slave-traders for his body. Bodily fear, not conscientious scruples, prevailed.”

At the tavern outside of Richmond, Listwell struggles with concealing his abolitionist views. He believes that it is his moral duty to denounce enslavement and experiences guilt when he says otherwise, even when it is necessary for his survival. This is another example of how Douglass develops the theme of presenting models of white allyship.

“Slave-gang […] Humanity converted into merchandise, and linked in iron bands, with no regard to decency or humanity! […] And all to fill the pockets of men too lazy to work for an honest living, and who gain their fortune by plundering the helpless, and trafficking in the souls and sinews of men.”

This quote develops the theme of The Horrors of Enslavement. Douglass lays bare the central project of chattel enslavement: to convert humans into “merchandise.” Enslavers shackled Black people, transported them from Africa to the United States, separated them from their families, forced them to work without pay, and sold them as possessions at enslavement markets. This practice allowed white enslavers to build their fortunes and maintain a racially segregated society.

“American Slave Trade […] how strange and perverse is that moral sentiment which loathes, execrates, and brands as piracy and deserving of death the carrying away into captivity men, women, and children from the African coast; but which is neither shocked nor disturbed by a similar traffic, carried on with the same motives and purposes, and characterized by even more odious peculiarities on the coast of our model republic.”

One of the horrors of enslavement is that American chattel enslavement was legal in the 19th century while other forms of enslavement were illegal. Douglass points out that it is hypocritical to condemn other forms of enslavement and condone the “peculiar institution” of chattel enslavement that keeps Black people as property.