Why You Can’t Win…

An underground classic, You Can’t Win, is a book worth hunting down- even if takes a little effort. Though in these days of Amazon and rare used book websites, that should shouldn’t be too hard to do. The book was a major influence on Beat writer William S. Burroughs, who wrote the introduction to the reprint. 

You Can’t Win is almost like an anti-On The Road. Instead of seeing the openness and romance of America as a quest for spiritual enlightenment, Jack Black hits the road (and rails) in search of gambling, stolen goods to fence, drugs and cynical criminal opportunities.

It’s the dark side of the American dream, and a haunting one at that. And unlike Herbert Asbury’s historical Gangs of New York, You Can’t Win is an autobiography that gives you the first-hand persoective on life in the darkest of trenches. You can almost smell the cheap whiskey, sawdust and split blood on the saloon floor.

Written by author Jack Black in 1926, it recounts his exploits as a young runaway, train riding hobo, jewel thief, safecracker, convict, gambler, and opium addict in the American West at the turn of the 20th Century. It gives his insider perspective on the underground criminal subcultures that flourished in those days: their slang, rituals, codes, way of life and hideouts. And this guy can write; you’ll have trouble readjusting to your boring life after stepping away from its pages.

It’s an incredibly unique book, I don’t think I’ve ever read anything quite like it anywhere, and without Black’s descriptive writing, his colorful and sinister world would probably would be all but forgotten to the mists of time. His description of staking out and robbing houses in pre-earthquake San Francisco, solitary confinement and flogging in a Vancouver jail, and his motley crew of associates: “Salt Chunk Mary”, “Montana Blacky” and “The Sanctimonious Kid” will all stay with you as real as yesterday.

His use of slang that criminals spoke only immerses you further into a place where few of us would ever dare to tread: Yegg (Safecracker), Hobo Jungle (Homeless Encampment), Dr. Hall (Alcohol), Yaffled (Arrested), Bulls (Rail Yard Cops) Skookum House (Jail).

“The thought of working to me was a foreign as the thought of burglary or robbery would be to a settled printer of plumber after ten years at his trade. I wasn’t lazy or indolent. 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. I didn’t call them suckers or saps because they were different and worked for a living. They represented society. Society represented law, order, discipline, punishment. Society was a machine geared to grind me to pieces. Society was an enemy. There was a high wall between me and society; a wall reared by myself, maybe–I wasn’t sure. Anyway I wasn’t going to crawl over the wall and join the enemy just because I had taken a few jolts of hard luck.”

― Jack Black

However, nor Black doesn’t glamorize his life and the choices that led him there. Indeed, the book is written as a warning to other criminals to go straight and reject the lifestyle that he lived for so many decades. In Black’s opinion, committing crime in the near future will become all but impossible with newly advanced methods of policing and criminal detection. Similarly, his nearly 15 years of accumulated jail time he sees as, ultimately, a wasted life. Hence the title: You Can’t Win. 

Towards the end of his days, Black gets out of the prison and the criminal life, sponsored by and working for the wealthy owner of the San Francisco Call newspaper. He went on tour around the country lecturing on penitentiary reform.

He also tried his hand at playwriting, creating the poorly received “Salt Chunk Mary”. And then… Black simply disappears from history, though it’s surmised that he committed suicide by drowning at the beginning of the Great Depression. Maybe the struggle of life just got to be too much for him in the end.

I actually gave You Can’t Win to my little brother some years back. He liked it so much, he got a massive tattoo of it on his arm (I’m sure my parents will thank me for this):

My brother explained to me that the outer arm at the top depicts a hobo making mulligan stew in his encampment, underneath is a obviously a steam train (the positives of freedom). The inner arm on the right depicts the negatives of a life of crime (death and imprisonment).

You don’t have to rush out and get tatted up like my brother did, but give this classic of counterculture literature a try. Are there any lessons to be learned from it? I’m not sure- other than you’re gonna lose before you leave the starting gate if you follow Black’s path. Still, it makes for a gripping, insiders view of a now long-lost subterranean/outsider culture.

And you: what’s your favorite tome of counterculture literature? What books inspire you?

4 thoughts on “Why You Can’t Win…

  1. this book is an old favorite. I’m glad you wrote about it, I found it and enjoyed it all over again 🙂

    • Post Author Greg Goldblatt

      Yeah, I really should give it a second read- I probably last went through You Can’t Win about 10 years ago. I’m sure I would find old favorite passages and characters I completely forgot about. Black’s descriptions of 19th Century prisons just sound like sheer Hell.
      There’s another companion book about a female hobo I often find recommended alongside it: Boxcar Bertha, but I’m afraid I’ve never had the pleasure. So many books- so little time sadly…

  2. Hi Greg,
    I love reading ‘Romantic Bohemian’ and showed this Blog to Glen, my husband, who immediately bought the book. Don’t think it is my kind of read but he is enjoying it tremendously. Thank you!

    • Post Author Greg Goldblatt

      Hey there Jane- thanks for the complement and I’m glad you’re enjoying the blog! You’re right, its not the kind of book for everybody, but I hope your husband finds himself thoroughly immersed in a seedy underworld full of cat burglars, train jumpers, hop heads and generalized turn of the century low-lifes. As long as he doesn’t get a massive tattoo like my brother, he should be able to emerge undamaged from the experience.

Leave a Reply

Your email address will not be published. Required fields are marked *