You Can't Win (book)

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You Can't Win
Author Jack Black
Published 1926
Publisher Macmillan

You Can't Win is an autobiography by adventurer Jack Black, written in the early to mid-1920s and first published in 1926. The book tells of his experiences in the hobo underworld, freight-hopping around the still Wild West of the United States and Canada. 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 book was a best seller in 1926. It has been republished several times.

The book has been adapted to film titled You Can't Win (2015) starring Michael Pitt who also wrote and produced.[1][2]

William S. Burroughs cited You Can't Win as an extremely influential book in his life, and lifts the book's style and stories in his 1953 book Junkie.[citation needed] The book was republished in 2000 in the Nabat series of radical autobiographies, by AK Press, with an introduction by Burroughs.

The topics and subcultures explored in You Can't Win are very similar to those explored in Edwin Sutherland's seminal classic of criminology, The Professional Thief (1937).[citation needed]


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. In his own telling, Black does not seem to have an especial weakness for addictions (for example, he did not become alcoholic himself), but he does describe the addictive allure that gambling and opium held for him in various stages of his life. He expresses an opinion that drug addiction is more psychological than physical; nevertheless, he also admits that breaking himself of a daily opium habit was the toughest battle of his life.

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 failing to elude it), fixing cases (which can be done from both sides, defense and prosecution), and the futility and self-defeat of penal systems that breed more criminality than they punish or prevent
  • The "wall" that criminals often sense between a law-abiding lifestyle and a law-breaking one
  • Pity, pride, and contempt, including the professional pride that some criminals feel in their "work", and the contempt that law-breakers and law-abiders sometimes feel for each other
  • Carelessness and hypocrisy among both criminals and noncriminals
  • Self-discipline or the lack of it
  • Conscience, motivations, habit, and the vagaries of chance

Publication history[edit]


  1. ^ "You Can't Win (2015)". IMDB. Retrieved January 23, 2015. 
  2. ^ Adam Chitwood (April 18, 2012). "Michael Pitt to Write, Produce, and Star in Adaptation of YOU CAN’T WIN". Retrieved January 23, 2015.