It was time for a re-reading of You Can't Win, Jack Black's autobiography. Maybe because I often wonder why intelligent people make bad choices in life. Why someone raised in a "decent" family will choose to go wrong. This book pretty much answers my questions and it's entertaining to boot. The timing of Black's adventures are the 1890's and early 20th century. A completely different time from Dillinger and Capone but I think with some of the same sensibilities. Thieves saw themselves as professionals. It's also easy see that many of the same social problems that abound now, homelessness and addiction, were much the same.
It's telling to admit that I had to buy another copy of this book. I had loaned my copy to someone who moved away and took the book with him. I usually wish that most of the characters that I read about had written an autobiography explaining the why they chose crime. I think as to the choice, if not the methodology and experience, they might say the same thing Jack Black says. The honest life the pay is too little and the demands too great; the criminal life excitement and "easy" money for the high life.
This book gives great descriptions of jails, penitentiaries, flop houses, hop houses, and other places in plain language that rivals any novel. Ah, to go on a binge with Salt Chunk Mary and to attend a "convention".