"The road was my home, and I knew every trick, every rail yard, every jail cell in the land." — Jack Black First published in 1926, You Can't Win is a raw, unflinching memoir from the underworld of America's early 20th century. Jack Black, a lifelong drifter, burglar, and safecracker, recounts his years spent hopping freight trains, dodging the law, and surviving in prisons from coast to coast. But this is not just a tale of crime—it’s a story of redemption. With gripping candor and unexpected wit, Black offers a rare window into the criminal class of his era, exposing the code, the culture, and the unspoken morality of life on the margins. You Can’t Win is as much a confession as it is a cautionary tale—proof that even the hardest life can hold the possibility of change.