You Can’t Win · Chapters

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Chapter companions for You Can’t Win by Jack Black.

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Chapter 1
Acknowledgments
The author dedicates the book to Fremont Older, Judge Frank H. Dunne, an unnamed friend who helped him escape from San Francisco jail, and a beggar named 'Sticks' Sullivan who removed buckshot from his back under a bridge in Baraboo, Wisconsin.
Chapter 2
You Can't Win
Jack Black reflects on his life of crime, the inevitability of capture, and the harsh realities of the criminal underworld. He recounts various experiences, including his time in prison and the betrayals he faced, emphasizing the futility of a life of crime.
Chapter 3
I
The narrator reflects on his transformation from a motherless schoolboy to a hardened criminal, contrasting his current role as a librarian with his past as a yegg and highwayman. He describes his bleak twenty-five-year criminal career, the loss of his mother at age ten, and his early departure from convent school at fourteen, which set him on a path of burglary and imprisonment.
Chapter 4
II
The narrator recounts his time at a Catholic convent school, where he forms a bond with the coachman Thomas, who tells him stories of Jesse James and other outlaws. He becomes fascinated with crime stories, especially after reading about Jesse James's murder, which fuels his sympathy for outlaws and his eventual turn toward crime. The chapter explores his internal conflict between religious devotion and admiration for lawless heroes.
Chapter 5
III
After leaving the convent school at fourteen, John returns to live with his father in a hotel, adjusting to a new, noisy life. He attends district school but struggles with arithmetic. He takes a job working for Cy at a bar, earning his first wages, and gains a sense of independence. The chapter ends with him saying goodbye to an old veteran before leaving for the city.

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Acknowledgments

You Can't Win

I

II

III