Writing the Rails: Jack Black’s ‘You Can’t Win’

“Hey you,” said George from across the fire, “you’re a liar.” His little dead blue eyes were blazing now like a wounded wild boar’s. “You was a good bum, but you’re dog meat now.” A gun flashed from beneath his coat, and he fired into Gold Tooth twice. Six feet away, I could feel the slugs hit him. His head fell forward and both hands went to his chest. He turned round, like a dog getting ready to lie down. His hat rolled into the fire. His hands were clawing the red-hot coals.

Welcome to a day in the life of the Johnson Family, a loose fraternity of burglars, safe-crackers, con artists, stick-up men and wild Civil War vets who traveled America’s railways in the 1890s, staying in one long enough to do a ‘job’, then moving on again.

The Johnsons’ bizarre underworld – its faces, rules and lore – would likely be lost to history if not for Jack Black, You Can’t Win‘s author. Taken in by the Johnsons in his youth, Black enjoyed a long career as a “yegg”: an elite safe-breaker, until the sloppy disposal of a cache of stolen jewelry landed him in California’s fearsome Folsom prison. Improbably, he emerged from that hellhole as one of America’s earliest true crime authors.

Check Out You Can’t Win by Jack Black at Amazon.

Black survived Folsom’s straitjackets and shankings, a fearsome opium addiction and even the San Francisco Earthquake of 1906 to finally go  straight at the end of his life, when he shared his tale with young reporter Rose Wilder Lane.

Lest anyone think he was fully repentant, he dedicated the book to “the unnamed friend who sawed me out of the San Francisco jail and to that dirty, drunken, disreputable, crippled beggar, Sticks Sullivan, who picked the buckshot out of my back under the bridge at Baraboo, Wisconsin.”

The book details Black’s life with his Johnson Family buddies – sample names: Smiler, Foot-and-a-Half George, Salt Chunk Mary and the Sanctimonious Kid – working town-to-town, carefully blending in with the ordinary hobos and ‘bindle stiffs’ who rode the freight trains. Spoils from the burglaries and bank jobs are ‘planted’ (buried) and picked up months later on a second trip when the heat dies down. It’s a rough life with a strict code of honor: never talk, never give your name, and always help a member of the Family.

Arrayed against the Johnsons are an army of trigger-happy small town cops, city detectives, brutal railroad guards, sadistic prison bosses and just plain bad luck – such as when Black returns to a ‘planted’ bag of stolen money to discover a house newly built over the spot. Famous faces occasionally make cameos; when Black and the Kid plan a heist on a card game, they’re forced to retreat hastily after spotting infamous OK Corral gunslinger Bat Masterson at the table, fully armed.

Packed with details on every criminal scheme from stick-ups to well-cased safecracking jobs, historians and outlaws alike will love this rough, tough rollercoaster of Wild West criminality and cat-and-mouse adventures. Joe Coleman’s dark illustrations and a foreword by rebel author William S Burroughs complete the package.

This is Black’s only book. After enjoying some small fame from it, he vanished into history. His end – and even his real name are uncertain – after all, a Johnson never tells. But what a story he left!

If you’ve ever enjoyed a show like Boardwalk Empire or Peaky Blinders, or a movie like The Sting or even Gangs of New York, this book deserves a place on your shelf – or better still, in your backpack.

Click here to buy You Can’t Win from Amazon today.

Prefer modern crime? Check out the Ozark underworld of Daniel Woodrell at Goods for Gents.