You Can't Win
Jack Black
1926

This classic account of a life lived at the edge was a major influence on Beat generation writers.

First Edition, Third Printing
You Can't Win is an autobiography by burglar and hobo Jack Black, written in the early to mid-1920s and first published in 1926. It describes Black's life on the road, in prison and his various criminal capers in the American and Canadian west from the late 1880s to early 20th century. The book was a major influence upon William S. Burroughs and other Beat writers.

The book tells of Black's experiences in the hobo underworld, freight-hopping around the western United States and Canada, with the majority of incidents taking place from the late 1880s to around 1910. He tells of becoming a thief, burglar, and member of the yegg (safe-cracking) subculture, exploring the topics of crime, criminal justice, vice, addictions, penology, and human folly from various viewpoints, from observer to consumer to supplier, and from victim to perpetrator.

 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.

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Black's book was written as an anti-crime book urging criminals to go straight, but it is also his statement of belief in the futility of prisons and the criminal justice system, hence the title of the book. Jack Black was writing from experience, having spent thirty years (fifteen of which were spent in various prisons in Canada and the United States) as a travelling criminal, and offers tales of being a cross-country stick-up man, home burglar, petty thief, and opium addict. He gained fame as a prison reformer, writer, and playwright. He disappeared in 1932 in a likely suicide.

--Wikipedia
394 pages

This copy has definitely seen better days but is still in readable condition

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