You Can't Win

 Black Jack. You Can't Win. New York : MacMillan 1926. Print.

First Sentences:

I am now librarian of the San Francisco Call. Do I look like one?

 

Description:

Hardly the opening sentence for the autobiography of a lifelong criminal, a thief who spent the greater portion of his life either stealing, incarcerated in jail, or on the run from police. But such is the start of this fascinating memoir from the author/criminal Jack Black in his 1926 book of detailing his life of crime, You Can't Win. Interestingly, this was a favorite book of William S. Burroughs, author of Naked Lunch, as well as several other Beat writers.

Black was born in the late 1800s and, after his mother died when he was 10, lived with his father in a hotel. Because his father traveled often for business, Black was placed in a Catholic school for four years until he aged out and returned to the hotel life. Unsupervised by his father for weeks, often months at a time, he obtained small jobs like collecting bills for the milkman and minding a tobacco shop (which the owner used as a front for illegal gambling). These jobs brought him in contact with former Civil War soldiers, drunks, gamblers, prostitutes, bums, thieves, and others who were, in his words, "bad men." 

 

At 20 he left "home" and began life as a "Yegg," that is, a beggar/thief, who hitched rides on trains, robbed homes, held up people by gunpoint, blew up safes, and was constantly on the lookout for "coppers."

My background is crowded with robberies, burglaries, and thefts too numerous to recall. All manner of crimes against property. Arrests, trials, acquittals, convictions, escapes. Penitentiaries! I see in the background four of them. County jails, workhouses, city prisons, Mounted Police barracks, dungeons, solitary confinement, bread and water, hanging up, brutal floggings, and the murderous straitjacket. I see hop joints, wine dumps, thieves' resorts, and beggars' hangouts. Crime followed by swift retribution in one form or another. I had very few glasses of wine as I traveled this route. I rarely saw a woman smile and seldom heard a song. In those twenty-five years I took all these things, and I am going to write about them. And I am going to write about them as I took them - with a smile.

After Black left home for the road, he met up with various other wandering men with colorful names such as "Smiler," "Foot-'n'-a-half George," "Salt Chunk Mary," "Soldier Johnnie, and "The Sanctimonious Kid." They taught him through example how to determine a source of money to steal, painstakingly prepare for all contingencies, investigate escape routes, execute the plan, and hopefully hop on a nearby train, leaving nothing behind of your presence in the town. All clothes used in a crime episode were always immediately discarded and any rental rooms cleaned out. Guns, seldom used except in stick-ups as a threat, were often thrown away as well, as they were cheap and readily available in those days. 

But the risks Black undertakes are high. Even with careful planning, things often go wrong. Statistically, burglars are successful only one in five attempts and are often shot at by homeowners or attacked by household dogs. Safes need to be exploded, the sound often raising the owners' interest and subsequent capture of the thief. Train guards were a constant threat as they were known to savagely beat up or even kill anyone they found jumping onto their trains for a free ride.

It was a grim life as well. Several of his fellow thieves were killed during a job with him. He was often jailed, waiting trial for months until shipped to a penitentiary for long-term sentences. He was betrayed by several people through their perjury in court, resulting in his convictions when there was little proof he committed the crimes. He endured solitary confinement, 30 lashes with a whip, and being bound up in a full-body straight jacket, a then-recently invented device that often drove prisoners completely insane after only a few hours trussed up in it.

He does meet people who are kind to him, whether fences, fellow prisoners, lawyers, judges, or simply people sympathetic enough to him to help him obtain legal help. He was even assisted in escaping several jail cells by friends who smuggled in files for him to saw through window bars. Once, he sawed for several nights under the nose of his drunk jailer. In several jails, he was given books from the prison library and passed the empty hours in his cell reading voraciously.

There is some ironic humor in several of his experiences. He and two partner picked the lock of their cell, left the jail and blew up a safe, hid its contents, then went back to their cells, achieving the perfect alibi. Once after two months' planning, Black blew a safe containing the local miners' weekly pay, but the exploded safe fell forward onto its door, thus preventing Black from opening it. He once buried a stash of stolen money in a vacant lot, only to return months later to claim it only to find a building had been constructed over his hiding place. In prison, he ordered cheap jewelry from mail order catalogs, then sold them at a profit to visitors who were told the items were "stolen stuff" smuggled into the jailhouse.

Although Black was twenty-five year thief, an opium addict, and Faro gambler, he brought an honesty and clarity to his world and the people he encountered. He was a thinker, whether in planning a job or wondering at length about the influences on a man which shapes his life, and how much one can control his own destiny. His writing in this autobiography is straightforward, thoughtful, and full of details that bring his world, the people he encountered, his jobs, and his personality into sharp focus.

Black does eventually give up his criminal life, kick his addictions, and secure lawful employment as a librarian no less. And with his former life behind him, he wrote this book. 

While this may not sound like an attractive read, believe me Jack Black is a wonderful writer with a compelling story to tell. You Can't Win paints a historical picture of the society of the late 1800-early 1900s that is both vivid and revealing.  I found this book tremendously engrossing and gets my highest recommendation for everyone.

The thought of turning to the right, squaring myself, and starting anew never entered my mind. Probably youthful egotism, which is nothing but confidence born of ignorance, whispered to me that I could beat a game I knew to be wrong and full of dangers....I knew I was wrong, and yet I persisted....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. That was the atmosphere I breathed. 

[If this book interests you, be sure to check out:]

 Lowrie, Donald. My Life in Prison

In the early 1900s, the author, after stealing a watch and purse valued at about $100 is sentenced to 15 years in San Quentin prison. In this fascinating book, he recalls his life as a prisoner, from food to riots to friendships and the strait jacket punishment that drove men insane. Brilliantly recorded, shocking at times, and revealing of a world, both positive and negative, that few of us know about. (Previously reviewed here)

 Happy reading.

Fred

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