Originally published in 1926, ‘You Can't Win’ is an amazing autobiography of a criminal from a forgotten time in American history by Jack Black, a burglar, safe-cracker, highwayman, and petty thief. The book recounts Black's adventures in the hobo underworld, freight-hopping around the western United States and Canada, with the bulk of incidents taking place from the late 1880s to around 1910. He narrates 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. It is a true lost masterpiece, one of the most legendary cult books ever published in America.