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You Can’t Win · Chapter

XVI explained

After spending a year in San Francisco, the narrator considers moving to New York but is dissuaded by a fellow traveler who warns of the city's dangers for outsiders.

What happens

After spending a year in San Francisco, the narrator considers moving to New York but is dissuaded by a fellow traveler who warns of the city's dangers for outsiders. He returns west, working through harvest fields and encountering yeggs and thieves. Winter drives him toward Vancouver, but he is arrested in Canada for a hotel safe burglary. In jail, he befriends a Chinese cellmate, learns Chinook, and plans an escape using smuggled hacksaws.

Themes in this chapter

  • Survival and Adaptability

    The narrator adapts to changing circumstances, from deciding against New York to working harvest fields and planning a jailbreak, demonstrating resourcefulness.

  • Alienation from Society

    The narrator feels isolated as an outsider in New York and later as a prisoner in Canada, relying on his wits and a cellmate for companionship.

Characters to notice

  • George

    Foot-and-a-Half George is mentioned in the narrator's stories to other travelers, recounting his finish and the narrator's getaway.

  • Mary

    Salt Chunk Mary is referenced as someone the narrator could have written to for money, but he chose not to.

Key passages

  • “It’s the toughest town in the United States for an outsider to get by in.”

    New York is extremely difficult for a stranger to survive in.

    A fellow traveler warns the narrator against going to New York.

  • “I can get dollars in the West where I couldn’t get dimes in New York.”

    I can earn dollars in the West but would struggle to make dimes in New York.

    The traveler contrasts the ease of earning in the West with the difficulty in New York.

  • “My prestige grew and I came to be accepted everywhere as 'Stetson,' which, in the language of the road, means first class.”

    My reputation improved and I was recognized as a top-tier traveler among hobos.

    The narrator gains respect on the road after sharing his story about Foot-and-a-Half George.

  • “If a Chinese doesn’t like you he will keep away from you; if he does like you he will go the route.”

    A Chinese person will avoid you if they dislike you, but if they like you, they will be loyal and helpful.

    The narrator reflects on his positive experiences with Chinese people, including his cellmate.

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