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'You Can't Win' (Annotated) With Glossary of Hobo, Tramp, and Transient Terminology

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'You Can't Win' is the pioneering American underworld memoir and proto-Beat classic written by Jack Black, a burglar, drifter and criminal active in early 1900's America.

In his striking, and often deadpan and humorous memoir, the author recaptures the transient underworld of the early twentieth century. In 'You Can't Win', the reader will meet unforgettable underworld characters as diverse and fascinating as: 'Foot and a Half George'; 'Salt Chunk Mary'; the Sanctimonious Kid; Soldier Johnnie; and many more. Black's astonishing accounts of hopping trains, cracking safes, escaping prison cells, and drug addiction offers an unusually vivid portrait of American underworld life over a century ago.

This all-new 2022 edition is annotated with accompanying bonus glossary of Hobo, Tramp, and Transient Terminology

William S. Burroughs first read You Can't Win as an adolescent and cited the book as influential in his life and writing, mentioning the autobiography in his 1953 book Junkie.

You Can't Win tells of Black's experiences in the hobo and criminal underworld, freight-hopping around the western United States and Canada from the late 1880's to the early 1900's. The book also is among the first to introduce the 'yegg' subculture, a prototypical form of criminal Hobo or bum prevalent in the USA around the turn of the century.

A must read for fans of true crime, American history, Beat writers, and hobo-yegg culture!

The main criminal activity of Black's life and of the book is thievery, which leads to discussions of various technical aspects of the thief's trade, including casing of prospects (surveillance of targets), safe-cracking, fencing of stolen goods, the disposal of evidence, maintaining aliases and avoiding attention or traceability, the social networks of criminals, the experiences of being arrested, questioned, and tried, and the experience of doing time in jails and prisons.

The vices and addictions Black discusses include alcoholism, abuse of opium ('hop'), gambling, prostitution, and stealing.

Themes that Black explores through anecdotes from his life include:

• Doing time in jails and prisons (and sometimes escaping from them)
• The criminal justice system, including eluding arrest, and fixing cases (which can be done from both sides, defense and prosecution
• The criminal community and their codes of conduct.
• Carelessness and hypocrisy among both criminals and noncriminals
• Self-discipline or the lack of it
• Conscience, motivations, habit, and the vagaries of chance

386 pages, Kindle Edition

First published January 1, 1926

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About the author

Jack Black

89 books3 followers
Librarian note:
There is more than one author in the GoodReads database with this name.
This profile may contain books from multiple authors of this name
For other authors of this name, see:


Jack Black - Actor, Musician
Jack Black - 1871-1932, Biographies
Jack Black - Motivational Speaker
Jack Black - Sociology, Cultural Studies

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Author 5 books2 followers
May 26, 2022
All new edition of the underground classic, featuring a fascinating glossary of slang and terminology used in that time period. Also, some of the racist period language was softened, making this edition more classroom-user friendly.
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