You Can’t Win : by Jack Black, 279 pgs. By Todd Taylor

Apr 13, 2011

No, it’s not an autobiography of the chubby dude with shaggy hair in the movies. You Can’t Win is neck-and-neck with Boxcar Bertha (see last issue), in fact, reading them in tandem gives the reader an extremely lucid view of the turn of the century in America from the bottom of the barrel, this book from the perspective of a lifetime thief. In its time, this book was a best seller, going through five printings in the 1920s, and much like Nelson Algren’s Walk on the Wild Side that was wildly successful and in turn virtually forgotten decades later, there’s a real humanity and a concerned depth of character to the people in the story. Jack Black’s no one “important” – he isn’t the owner of a railroad, a doctor, a senator, or a general – but his story, of coming from a broken home, being “raised” by his father, and his slow, meandering lifelong induction and involvement in both the hobo and yegg (criminal) lifestyles, is tinged with timeless qualities that make the book extremely relevant and topical, especially today. When I read this book, I couldn’t help but think of folks like Howard Zinn and Studs Turkel – historians who understand the importance of letting the “little” people speak in their own voices and air their concerns.

You Can’t Win is a great look at the inside of a loose criminal organization and a close examination of one professional thief’s code of ethics that conscientiously isn’t full of hyperbole. The book reads in a very even tone, which is surprising since it’s rich in experiences could easily be morphed into a movie with lots of explosions and intrigue. Thankfully, it reads honestly. There’s no doubt that Jack did wrong things – like stealing a (fake) ruby, breaking open a copious number of safes, and often creeping into people’s rooms (once a champion boxer) at night when they slept. He self-admits that, but he did these illegal actions in a way that was consistent for him, a man who became incapable of taking a straight job. Ethics? Can a thief have ethics. Yes. Jack explains: “The thief who goes out and steals money to pay back room rent rather than swindling his poor landlady has character. The one who runs away without paying her has no character.”

For this review, I’m going to hold Jack Black to a higher standard than what’s clogging up the book charts. Instead, I’ll consult a higher source – the Dwarves’ classic album: Blood, Guts, and Pussy. Let’s take a look

 Blood: There’s a lot of blood. Lots of folks get shot and killed. Occasional chunks of skull fly from close-range shotgun blasts. In one instance, a fellow train hopper and Jack get into a boxcar filled with lumber. When the train hit a downgrade, the lumber shifted: “The boy had died instantly. His body, from the waist up, was flattened between the lumber and the front end of the car.” Jack was imprisoned from above by the lumber, and cut his way out of the boxcar with a pocketknife. This is much more engaging than reading about people stuck in cubicles, having conversations in a mall, or complaining that there’s a downside to fame.

Guts: There’s no question that Jack was brave, but later on in life, his digressions against the state began accumulating and he had to suffer longer prison sentences and severe beatings. Roughly, the last third of the book is a look into the prison system (which hasn’t changed all that much in eighty years, truth be told) and details a whipping when he’s tied and stretched up on a tripod and beaten with a leather strap: “The first blow was like a bolt of lightning; it shocked and burned.”

Pussy: I have to credit co-Razorcake dude Sean for bringing this up. This book is, oddly, virtually devoid of sex. Sure, there are prostitutes lurking about, but not once – to my recollection – does Jack size up a woman, invite a woman to spend an evening with him, nor comment on a woman’s shape. I even thought about the possibility that Jack was gay, but, being in prison, he would have ample time to pursue male tail in the joint. First-hand sex never reaches these pages. I’m still wondering why. Was Jack asexual or was it a publishing decision not to go against the mores of the times? So, in place of pussy, Jack Black delivers with drugs, which he slowly became addicted to. He claims “I discovered that the finest quality of morphine may be obtained from lettuce and proved it in the prison garden by extracting it and eating it.” This, I did not know.

All in all, if I were to become the Czar of Reading and there were required texts you had to read before being let out into society at large, You Can’t Win would definitely be in the top hundred. Not only is it well-written and easy to read, it’s got the weight of a man’s heart in it and the power of eighty years lapsing to show that history may have happened in the past, and there’s a lot to learn from it, but due to the themes that Jack presses that haven’t been resolved, history sure as hell isn’t over. –Todd (AK Press, PO Box 40682, SF, CA 9410-0682)

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