A Reformed Thief and Safecracker Shares His Personal Story of Crime and Redemption


You Can’t Win – Jack Black (1926)


            Books are magic.  Every time I enjoy a new one I am reminded of this fact.  Before humans assigned symbols to the sounds made as they spoke, all knowledge and information was dispersed orally.  For you to learn how to braid rope, for example, you had to live near someone who knew how to braid rope, and have them teach you the technique through spoken words and physical demonstrations.  This allowed knowledge and wisdom to pass along familial and then tribal lines, as humans shared their ever-growing store of knowledge with their offspring and neighbors.  Everything changed once humanity figured out how to use symbols to communicate information.  This was a change infinitely more monumental than the current change from physical media (books, magazines, DVD’s, LP’s) to digital file-storing media. 

            The ability to write down your experiences, have them printed or published, and put them out into the world at large changed us for the better. It removed the old taboos about sharing knowledge with outsiders.  Anyone can pick up a book by Mark Twain and gain a deep understanding of what life was like at the time he wrote his books.  This is time-travel, pure and simple.  A human consciousness reads the symbols on the page, and instantly, they are conversing in a very real manner with a person from the past.  Far too often humans assume that everyone’s lives are the same, that what happens to “me” is bound to happen to “you” as well.  This is a fallacy.  The world is so infinitely complex that no two individuals, even if identical twins, will have the same life and the same experiences.  Reading personal memoirs and accounts helps us realize the infinite variety of human life, and human experience.

            I found this book while scrolling through the Project Gutenberg website (I love Project Gutenberg!!).  Jack Black wrote a memoir about his life and his long-standing years as a Bum and Thief, riding the rails, visiting Hobo encampments, and surviving on the fringes of society.  He travelled multiple times across the US, and into Canada.  He describes his life and its many ups and downs in an honest, heartfelt matter, never bragging about the crimes he committed, or the people he stole from.  Instead, he often discusses reaching crossroads in his life, moments and situations where he could have chosen to go “straight,” and instead went back into the transient criminal life.  He also covers the “mistakes” he made, times when his greed or hunger got the best of him, despite the many warnings given and lessons taught to him by older road-warriors.

As with any and all memoirs, these tales must be taken with a grain of salt.  Our narrator is a self-defined criminal, transient, and ex-convict.  While he does not shy away from bluntness when it comes to himself, it is inescapable that such an author would omit specific details, either to protect himself, or someone close to them.  Even so, Jack Black’s account of his life does not hide away the self-reflection, understanding, and wisdom gained through suffering and hardship, even the self-created kind.  It makes perfect sense that, in reading about this book, I found out it was a seminal piece of writing for many of the Beat poets, William S. Burroughs specifically. Black’s tales of riding the rails, escaping police, finding big scores, losing big scores, and the general ability to live an outlaw life appealed to the counterculture writers of the 40’s and 50’s. 

As with many things, such a life was much easier to achieve in the past.  Small towns did not have the type of bank safes, police, or any other preventative to deter petty crime.  Mr. Black details the many methods he used in acquiring a “bank roll.”  From pickpocketing and petty thievery, to burglary, breaking and entering, and safe-cracking, it appears that not a single moment was spent in leisure activity. Every second was either an attempt to get information on a new mark, casing out a joint to either rob it or help someone else rob it, finding out the best “hop-joints” in town (for 25 years Jack Black nursed an addiction to smoked opium), secreting away stolen material, laying low for days or weeks until the stolen goods can be safely recovered, finding people to buy such stolen goods, etc.  It is a busy life, and Jack Black himself states that if any of his fellow “yeggs” (thieves specializing in safecracking), and hobos would just get a normal square job, they would have had far more free time, leisure, money, and prestige after ten years than what normally happens a decade into that outlaw life.  However, the goal is not safety and societal prestige.  It is complete and total autonomy.  To live in total autonomy in America means becoming an outlaw.  The government does not allow one to live without oversight of a thousand kinds, or so felt Jack and his fellow rail riders.

While Black was definitely a criminal, he details repeatedly the many ways that their subculture would provide and look out for each other.  They were fastidious about paying their debts to one another.  Those that did not were quickly ostracized.  This meant that every time Black scored big, he would first off send money to various people whom he owed, whether it was someone doing time in Folsom prison, or some kind underworld person that had previously lent Black some money or assistance.  As Black put it, an honest hobo would give you his last dollar if you needed it.  He details many occasions were this was true.  He also describes the kindnesses paid to him by his fellow rail-riders.  Once, while serving a long term in an unfamiliar prison, Jack began to receive care packages with food and money.  He did not find out who paid him this kindness until way later, and he busted his ass to repay every cent of it.  When you live on the rails, you own nothing, and your only collateral is your word.  Are you an honest thief?  Do you pay back your debts?  Do you keep your mouth shut?  These traits are far more valuable than a fancy car or a big home when you live life outside of normal society.

Jack Black wrote only one book, this one, after ten-plus years going straight, working as a librarian in a newspaper office owned by and old friend.  It became a giant bestseller, affording him an affluent life he never dreamed of.  The 1920’s saw a rise in the popularity of “true tales” of crime, prisons, and all aspects of the underworld.  It was not to last and the transient life does not provide lessons in saving and frugality.  The Great depression destroyed the last of his wealth and he sadly committed suicide sometime in the late 1930’s.

Reading “You Can’t Win,” it was evident that the author was an intelligent, conscious human being, despite all the obvious flaws of a criminal life.  I believe he owes it to his life-long love of reading and learning.  During an early stay in a Canadian jail, far out in the country, he found the jail to have a tremendous library, containing all of the best English authors.  He devoured these books.  In this jail, a very interesting policy was in effect.  Based on an English method, the entire population of inmates was kept silent.  Any speaking was met with severe punishment.  Ironically, it is this jail that Black describes as the most peaceful, safe, and orderly he ever saw.  There were no beatings, no fights, and no contraband because without the ability to speak to each other the inmates could not plot or set up schemes.  The only options for the prisoners were reading the classics, or silent contemplation of their lives and crimes.  I wish the USA would try this method, but it probably works only in jails or prisons containing 200 or less inmates.  In a world that currently seeks to close libraries, both public and in prisons, and to prevent access to books and ideas, Jack Black’s words of warning are key.  He states that a world that focused on inmates reading, expanding their minds, and creating new dreams, such as the jail in Canada, would do more to stop crime and suffering in the world than a thousand lashes.  At one point, sometime during a different decade-long stay in prison, he discusses reading an entire Encyclopedia Britannica, something I tried to do in Middle School.  Books can help you create yourself anew.

It is nearly one hundred years since this book was published, and I was able to find it as it is now in the public domain, and the wonderful saints at the Project Gutenberg provided all of us with a digital version.  Jack Black is immortal.  He now lives in my head, and in anyone’s head who’s read this great book.  I highly recommend it.

(This book can be downloaded here: https://www.gutenberg.org/ebooks/69404 )

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