You Can’t Win · Chapter
XIX explained
Jack Black reflects on his criminal past and the possibility of rehabilitation, travels to Vancouver and the Kootenai mining district, seeks Salt Chunk Mary in Pocatello only to find she has disappeared, and shares his observations on the o
What happens
Jack Black reflects on his criminal past and the possibility of rehabilitation, travels to Vancouver and the Kootenai mining district, seeks Salt Chunk Mary in Pocatello only to find she has disappeared, and shares his observations on the opium habit and the uncertainties of a burglar's life.
Themes in this chapter
Criminal Identity and Rehabilitation
Jack Black addresses ex-convicts directly, arguing that the will to quit crime is more powerful than external obstacles, and reflects on his own tempering through hardship.
Addiction and Self-Destruction
Jack Black discusses his own opium use and argues that the drug habit is largely mental, based on his observations of other addicts.
Survival and Adaptability
Jack Black adapts to life after prison, quickly earning and squandering money in mining towns, and navigates the uncertainties of burglary.
Characters to notice
- Chew Chee
Jack Black notes that Chew Chee did not appear in prison and likely quit stealing to go straight.
- Mary
Jack Black returns to Pocatello seeking Salt Chunk Mary, but learns she sold her place and disappeared over three years ago.
- George
Hannibal, an old acquaintance, knew of Jack Black's connection to Foot-and-a-Half George, who was killed.
Key passages
“Each of us must be tempered in some fire. Nobody had more to do with choosing the fire that tempered me than myself, and instead of finding fault with the fire I give thanks that I had the metal to take the temper and hold it.”
Everyone must undergo trials that shape them; I chose my own path and am grateful I had the strength to endure and be transformed by it.
Jack Black reflects on personal responsibility and resilience in the face of a criminal past.
“The other con who comes out time after time saying to himself cold-bloodedly and calculatingly, 'I won't quit,' might change his mind sometime and say, 'I will quit.' When he wills it, he does it, and no copper snitches him out of his job.”
An ex-convict who repeatedly resolves not to reform may eventually decide to quit crime, and that decision alone can lead to success without interference from police.
Jack Black emphasizes the power of will in rehabilitation.
“You can plan and plot and scheme; you can figure out just what you'll do from the minute you step into a place till you step out of it, but the great weakness of it is—you can't tell who or what is going to be outside when you go out, and all your ingenuity can't overcome it.”
No matter how carefully you plan a burglary, the unpredictable nature of what awaits outside the door is an insurmountable risk.
Jack Black describes the inherent uncertainty and danger of a burglar's life.