You Can’t Win – Jack Black

(Reviewed by JD Jung)


“From the day I left my father my lines had been cast, or I cast them myself, among crooked people. I had not spent one hour in the company of an honest person. I had lived in an atmosphere of larceny, theft, crime. I thought in terms of theft. Houses were built to be burglarized, citizens were to be robbed, police to be avoided and hated, stool pigeons to be chastised, and thieves to be cultivated and protected. That was my code; the code of my companions.”

However, he also admitted that the “murder” of Jesse James had a huge impact on him as a boy. Jack Black lost his mother when he was ten, and left school when he was fourteen. At age nineteen he was on trial for burglary, but acquitted. At twenty five he was burglarizing houses, and at age forty he was an escaped convict and fugitive. But when he wrote his 1926 autobiography, You Can’t Win, he was in his 50s and a librarian at a San Francisco newspaper. So what happened in between that time?

In his book he chronicled his life of crime, hopping freight trains in the United States and British Columbia where he was born. He graduated to robbing poker games, jewelry stores and more. “I knew there were lots of easier and safer ways of making a living but they were the ways of other people, people I didn’t know or understand, and didn’t want to…. They represented society. Society represented law, order, discipline, punishment. Society was a machine geared to grind me to pieces.”

He did have people he respected and trusted, though. Most were criminals, like Madam Singleton, Sanctimonious Kid, Salt Chunk Mary, Foot-and-a half-George and Smiler. Readers will learn all about them in the book. There was another group of people that he trusted, as he wrote, “underworld beggars are the most reliable and trustworthy, the most self-sacrificing and the quickest to help of any class of people outside the pale of society.” He always repaid the loyalty and kindness of others, which was more than just honor among thieves.

You Can’t Win was recommended to me by a clerk at the Beat Museum in San Francisco. So why is this autobiography and cautionary tale so significant to our cultural history?

It had a huge influence on the writers of the Beat generation, like William S. Burroughs who expressed his feelings in the foreword of the book. This is even though it took place in the late 1800’s and at the turn of the twentieth century. As you probably have already figured out, it appealed to those you felt like outsiders or who were living on the fringe of society.

Don’t forget to read the Afterword, as it reveals some additional information on Black’s life and mysterious death. An added bonus to this edition is Black’s 1929 article, “What’s Wrong with the Right People”, an editorial on the issue of crime and punishment.

I personally found You Can’t Win fascinating from a historical context; I learned about the hobo and drug subculture as well as  the prison system of the time. I was amazed how some institutions haven’t changed in more than a century. Black’s story itself was riveting. He detailed the relevant aspects of his life, while leaving out the trivial stuff. There were no tedious parts of the book and you got a real sense of who he was. He didn’t make any excuses for himself, and  took complete responsibility for his actions.

You Can’t Win is  part of the Nabat book series “dedicated to reprinting forgotten memoirs by various misfits, outsiders and rebels.” Jack Black’s story definitely falls into that category. It represents a chunk of American history that most of us will never learn about.


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