The True Crime Autobiography of an Early 20th-Century Thief and Dope Fiend Jack Black's 1926 bestselling true-crime memoir inspired generations of counter-cultural writers, including William S. Burroughs. William S. Burroughs first read the book as an adolescent and cited You Can't Win as influential in his life and writing, mentioning the autobiography in his 1953 book Junky. A major motion picture starring Jeremy Allen White, Michael Pitt, and Julia Garner! In this enhanced edition, you will find: Full text of the 1926 novel Introduction by the Editor 24 Illustrations Glossary of Criminal Terminology Historical Newspaper Articles about Jack Black. You Can't Win is a raw, honest journey through the criminal underbelly of early 20th-century America, from boxcar hopping to safe-cracking, from opium dens to prison cells. Written with surprising literary skill and devastating honesty, it presents a unique historical document of a vanished underground criminal world and the code by which its members lived and died. This remarkable memoir also serves as a valuable historical document, offering vivid descriptions of turn-of-the-century America from a unique perspective.

From the bustling streets of San Francisco to the remote mining towns of the Northwest, from crowded prison cells to lonely hobo camps. Black's narrative begins with his early years at a Catholic school, where he first encounters the strict authority that he would later rebel against. Following the death of his mother and subsequent abandonment of a stable home life, young Jack falls in with a seasoned criminal named "The Smiler," who becomes his mentor in the arts of burglary and survival on society's margins. What follows is an education in the criminal underground that reads like a masterclass in the techniques and ethics of professional thieves. The book's final chapters, detailing Black's eventual reformation and integration into legitimate society, provide a satisfying conclusion to this epic journey. Through the intervention of a newspaper editor named Fremont Older and a sympathetic judge, Black finally finds his way to an honest life. His transformation is all the more powerful for being hard-won and unsentimental.