After Soapy fails to get himself arrested for harassing a young woman in front of a police officer, the narrator captures his experience using both a metaphor and a paradox, as seen in the following passage:
With the young woman playing the clinging ivy to his oak Soapy walked past the policeman overcome with gloom. He seemed doomed to liberty.
In the first sentence, the narrator metaphorically compares the young woman—who, it turns out, is a sex worker—to “clinging ivy” and Soapy to an oak tree. This metaphor helps readers understand how, rather than feeling threatened by Soapy’s advances, the woman reciprocates them, as she is a sex worker hoping to earn some money. Even as Soapy walks away, the woman “clings” to him the way ivy clings to trees. This metaphor communicates how the sex worker's desperation to earn income is similar to Soapy’s desperation to get arrested, demonstrating how both of these impoverished “criminals” are just trying to survive.
The paradox in this passage is found in the narrator’s contradictory statement that Soapy “seemed doomed to liberty.” The contradiction emerges from the fact that most people—including Soapy—strive to have liberty and often feel doomed not to have it. The statement makes sense, of course, in the context of the story—“liberty” for Soapy means living (and quite possibly dying) on the freezing streets of New York, whereas confinement means having access to warm living conditions and consistent meals (in prison). This paradox is O. Henry’s way of highlighting how so-called “liberty” is not experienced the same way for people of different socioeconomic classes in the United States.
