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You Can't Win, the cover of this edition

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Trama e riassunto di You Can't Win

8 min di letturaAudio a breve8 punti chiave
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A chi è rivolto

This book is for readers who love true tales of the Old West, hobo life and outlaw slang, and for anyone curious about how prisons shape people and how a person can change course.

Che cos’è questo libro

How does a boy who prays for a swearing wagon driver end up cracking safes, smoking opium and serving time in four prisons? Jack Black answers in You Can't Win. He is the librarian of the San Francisco Call when he begins, and he studies his face in the mirror.

This is Black's own account of about twenty-five years in the American and Canadian underworld, written in the 1920s with the help of the editor Fremont Older.

In questo riassunto

  1. 1A motherless convent boy meets crooked lawFree
  2. 2Life on the road teaches hobo rules and loyalty
  3. 3Smiler's death sends him into a prison school
  4. 4Sanc teaches that careful thinking is a thief's craft
  5. 5George and Salt Chunk Mary keep an outlaw code
  6. 6The lash in Canada hardens a young thief
  7. 7Greed, a betrayal and Folsom nearly break him
  8. 8Two men's kindness turns a convict toward work

Punto chiave 1 di 8

A motherless convent boy meets crooked law

Black's mother dies when he is ten. His father, a silent railroad man, cannot manage a child, so he sends him to the Sisters. The world reaches him through Thomas, the old Confederate coachman, who worships Jesse James. When Thomas reads that James has been shot by a traitor, the boy takes the newspaper from the Superior's desk and passes it around the school.

Soon he reads nothing but crime stories. He sides with the hunted man every time. Black says plainly that these stories turned his thoughts toward adventure and then toward crime.

At sixteen he works in a Kansas City cigar store that fronts a gambling room. One evening he waits in the hall of Madam Kate Singleton's house when the police burst in. A hog farmer claims a girl named Julia robbed him. At the station the money turns up in the farmer's own coat pocket, and the lawyer, the captain and the women all walk out friends. Only the boy, guilty of nothing, is locked up. A well-spoken inmate tells him it was a setup, and the idea takes root that the law and the lawbreakers are partners.

The road to crime starts small, with a hero picked at the wrong age and a lesson that power and crime can sit at the same table.

That’s 1 of 8 key points.

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About this edition

Every format is free to start, and print and large print are at cost.

  • LengthAbout 115,200 words
  • Reading timeAbout 8 h 5 min
  • FormatseBook, large-print eBook, audiobook, 15-minute summary; paperback, hardcover and large print at cost
  • LanguagesEnglish and 13 other languages

Questions about You Can't Win

What is You Can't Win about?

It is Jack Black's memoir of about twenty-five years as a hobo, burglar and prisoner in the American and Canadian West, and of how he finally left crime and became a newspaper librarian.

Is You Can't Win a true story?

Black presents it as his own life story, told in the 1920s. Some names and details are disguised, and the book is best read as a first-person memoir from a man who knew the underworld.

What do the slang words like yegg and jungle mean?

A yegg is a tramp thief who breaks into safes. A jungle is a camp where hoboes cook, wash and sleep, often beside a railroad. Black explains such terms as they come up.

Who are Smiler, Sanc and Foot-and-a-half George?

They are the older thieves who teach Black his trade. Smiler is a cheerful burglar, Sanc a careful and educated planner, and George a tough, loyal safecracker with a damaged foot.

What is the main message of You Can't Win?

Black argues that crime costs more than it pays, that brutal punishment breeds more violence, and that kindness and a real chance to work can change a person's course.

Cite this edition

Black, Jack. You Can't Win. Library of Alexandria, 2026, libraryofalexandria.com/products/you-can-t-win.

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