You Can’t Win by Jack Black is a memoir of life among the “yeggs,” an American subculture that existed for decades in the early twentieth century, with tens of thousands of members pretty well hidden from the society at large. Today, the slang term “yegg” has become synonymous with “safe cracker.” A hundred years ago, yeggs were vagabonds who traveled by hopping freights, convened in the hobo jungles that sprang up on the outskirts of towns that had railroad yards, and lived primarily by committing small-time theft.
Some were pickpockets. Some were house burglars. Some specialized in safe-cracking. Some were explosives experts. Some ran crooked gambling games. Some specialized in robbing gamblers. Most spent large portions of their lives in prisons and jails.
This book has more plot twists than an Agatha Christie mystery and some of the most memorable characters you’ll find in literature. But it’s not a novel; it’s a memoir. The author is painfully frank about the details of his life, neither glorifying his adventures nor apologizing for his transgressions.
Some of the scams he pulled off both by himself and with partners are literally works of art—living theater at its finest. Example: Black and his partner find a jewelry store that has large crowds on Friday nights. There are numerous long display cases throughout the store, and many clerks are hired to stand behind the cases on Friday nights to show the merchandise to prospective buyers.
The scene is noisy and chaotic. Many of the clerks do not know each other as there are so many of them and it’s part-time work. Black’s partner gets decked out in a suit exactly like the suits worn by the clerks. He walks in and takes a place behind a display case. Black comes in acting like a customer and his partner starts bringing trays of jewels out to show him. Did I mention that Black was carrying what appeared to be a normal parcel, but was actually a box gaffed with a false bottom so that Black could nonchalantly walk out of the store with a whole tray of jewelry? Can you imagine pulling off something like this?
Some of Black’s adventures are hair-raising. He describes in detail how the house burglar works—first locating a victim who is known to have a large amount of money or jewelry in his home. Then, staking out the house to ascertain the victim’s schedule, how many people are living in the house, whether or not there’s a dog, determining the safest and most efficient escape route, etc. Then, waiting for hours outside the house until the occupants have had lights out for at least two hours so you know they’re in their deepest sleep. Then finding a way into the house—an unlatched window in most cases. Black describes spending an hour or more just going up a flight of stairs so as not to creak the wood, and rummaging around the bedrooms where the victims are asleep, while listening to the sleepers’ breathing rhythm.
I’ve been hooked on books by and about scammers, con artists, and crooks—fascinated by their freedom—since I first started to read. You Can’t Win ranks up there with the best of them. Initially published in 1926, it was out of print for decades, but was republished in 1988 with an Introduction by William S. Burroughs, in which he said he’d been fascinated as a teenager by this glimpse of an alternative life.
Like Burroughs, I was enthralled by how different Black’s world was. No one had an ID card. There were no drivers’ licenses, no social security numbers. If things went wrong in one town, you could hop a freight to the next town where no one knew you. Your name was whatever you said it was. No one in jail or prison ever gave their real name. At any time you could start a new life. As Black says:
Only the large cities attempted anything in the way of identification. The Bertillion system was in the experimental stage and fingerprinting unknown in police work. We jumped from one state to another, kept away from the cities, lived almost entirely on the road except in the dead of winter, and spent our money in the jungles…
As a professional gambler myself, it was fun reading how similar the yegg’s concerns a hundred years ago were to the concerns of the professional gambler today. Many of Black’s schemes took days, weeks, even months of planning, as he was trying to mentally cover all the angles. He was constantly aware of anyone who might be able to identify him, always ready to make a quick exit. He had to depend on partners who sometimes weren’t dependable. The amount of effort put into subterfuge, acting, costuming, and rehearsing on a single job is described vividly. Even after being captured by police, the yegg never stopped scheming. On more than one occasion Black escaped from custody and also helped friends escape from jails.
Black also discusses the code of honor the yeggs lived by. They considered themselves a family, up against the world. They wouldn’t steal from each other and the worst thing they could be called was a “stool pigeon.” They would put their lives on the line for each other and would do years in prison rather than rat on a partner.
Jack Black was 50 when this book was published in 1926, at which time he was working as a librarian in San Francisco. Born in 1876, he left home in 1892 at the age of 16 and began his life on the road. He lived this life for more than twenty years and likely would have died in prison had it not been for a San Francisco newspaper mogul, Fremont Older, who met him when Black was serving time in San Quentin. Older discovered how intelligent Black was—he’d educated himself in the prison library—and arranged for Black’s 25-year sentence to be cut short, then gave Black a job with one of his newspapers.
Black had been out of trouble and working in San Francisco for 13 years at the time You Can’t Win was published. The book did well, with five printings, and Black started working the lecture circuit, where he sought to inform people about the sadistic and corrupt prison system.
The book concludes with an excerpt from a 1929 article Black wrote for Harpers magazine lambasting the evils and ultimate failure of the U.S. prison system. You’ll notice that not much has changed.
In 1932, just six years after You Can’t Win was published, Black disappeared. His watch, a prized possession that had been given to him by an ex-con he helped, was later found at a pawn shop, but no one ever learned what happened to Black. I can’t help feeling he missed his freedom.
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