Jack BlackJack Black (1871-1932) was a hobo and professional burglar. Born in 1871 in New Westminster, British Columbia, [1] he was raised from infancy in the U.S. state of Missouri in the town of Maysville and eventually Kansas City. He wrote You Can't Win (Mcmillan, 1926), a memoir or sketched autobiography describing his days on the road and life as an outlaw. 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. Read More Read Less