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You Can’t Win · Chapter

XVII explained

After escaping from jail, Jack Black and his Chinese cellmate Chew Chee travel to Vancouver.

What happens

After escaping from jail, Jack Black and his Chinese cellmate Chew Chee travel to Vancouver. Black grapples with his ingrained criminal code, refusing to take money for helping Chew Chee and instead planning a burglary of a Chinese storekeeper's money. He attempts to use chloroform but fails, leading to his arrest. After escaping again, he searches for Chew Chee in Chinatown, eventually meeting a Chinese contact who leads him to a loft where he observes opium smoking. The chapter explores Black's internal conflict between his criminal upbringing and moments of moral hesitation.

Themes in this chapter

  • Criminal Identity and Rehabilitation

    Jack reflects on his ingrained criminal code, stating he thought in terms of theft and lived among crooked people, yet hesitates to use chloroform, showing a conflict with his identity.

  • Survival and Adaptability

    Jack adapts to escape jail, travel by freight train, and navigate Chinatown to find Chew Chee, demonstrating resourcefulness in dire circumstances.

Characters to notice

  • Jack Black

    Narrator and protagonist; reflects on his criminal code and attempts a burglary using chloroform, then escapes jail and searches for Chew Chee in Vancouver.

  • Chew Chee

    Jack's Chinese cellmate who escapes with him; later sought by Jack in Chinatown.

  • Sanc

    Mentioned as a knowledgeable figure who never taught Jack about chloroform.

Key passages

  • If you live with wolves, you will learn to howl.

    One adopts the behaviors of the people they associate with.

    Jack uses this proverb to explain how his criminal environment shaped his own actions.

  • I was practical, I knew nothing about chloroforming people. Sanc had never once mentioned chloroform and what he knew about burglary was plenty.

    Jack admits his lack of experience with chloroform, contrasting it with Sanc's expertise in burglary.

    Highlights Jack's reliance on learned criminal knowledge and his hesitation to use unfamiliar methods.