You Can't Win
John “Jack” Black was an American outlaw in the old west specializing in burglary, safe cracking and stick ups. I found out about his autobiography You Can’t Win bored one night googling William S. Burroughs favorite books and found this article. My interest was immediately peaked and before finishing the article I searched youtube for the audiobook and dove in.
“If you lay with wolves soon you’ll learn to howl.” - Jack Black
Jack was born in Canada and raised in Maysville, MO by his widower father who was a good man by Jack’s account, but not built to wrangle and raise an industrious free spirit such as himself. Jack went to a good boys school in Maysville and with this could have done just as well for himself as a straight citizen. All that changed when Jesse James died and he read the tales of Jesse and Frank in the local paper, much like Burroughs who read You Can’t Win at the tender age of 12. Both young and impressionable, they now had a code.
“Even at that age I had stumbled upon one truth, and that is, the best way to get misinformed is to ask a lot of questions.” - Jack Black
You Can’t Win is an American heirloom filled with tales of the golden age of thievery and the outlaw lifestyle. Something that is almost completely lost spare the pop culture obsession with Rap music, which is the last real form of in your face transgression. What our current outlaws lack is as far as I can tell is a code. Snitching was even a problem (and slang) in the old west, Jack talks glowingly about The Johnsons, which is a catch all for anyone who is good for it. Most of the Johnsons were thieves of course, but even a “copper”, a bank teller or a maid could be a Johnson. Lacking the energy to dig up an exact quote I found this Burroughs quote about the Johnson’s from this blog:
The Johnson Family’ was a turn-of-the-century expression to designate good bums and thieves. It was elaborated into a code of conduct. A Johnson honors his obligations. His word is good and he is a good man to do business with. A Johnson minds his own business. He is not a snoopy, self-righteous, trouble-making person. A Johnson will give help when help is needed. He will not stand by while someone is drowning or trapped under a burning car. - William S. Burroughs, The Dead Road.
Are there still Johnsons out there? I wonder. I believe I’ve run into a few; the two bearded old men who helped me charge the battery on my failing Honda Magna, “Big Sexy” a softball player who paid for my sweet tea when the card reader failed at 7-11…
This book is filled with outdated (but still fascinating) tales of burglary, prison escapes, safecracking and much more. He talks about the old old San Francisco and Seattle, Chicago and New York City, which he avoided in his thieving days by warning of another thief who basically described the setting of The Gangs of New York (there is a book the movie was based on) which was not hospitable to lone thieves of the craft.
The book tells of jail and prison life of the time. He broke out of more than a few jails, but not a Canadian prison which had him locked down for two years (rare for Jack). He describes this particular Canadian prison as being extremely regimented and well maintained compared to prisons in America. No speaking was allowed, but you always got fed and got to read as much as you liked. It sounds like Canada post Covid 19, but maybe that’s the outlaw spirit speaking through me… Jack Black is very self aware, and points out multiple times that he knows the life he’d led was “technically” wrong. He had this to say while awaiting lashings and reflecting on dead friends and misfortune:
“[…]I was the most miserable of them all and human like I tried to fix the blame for all my troubles on someone else.”
Is there still an Outlaw spirit in America beyond people saying faggot on twitter and considering themselves “the new avant garde”? I’ve already answered this and it is Rappers. Pretty much anyone with pale skin is a bitch (or non pale but might as well be) and thinks they’re fighting the good fight. Listening to this book has me wanting to do something bad. More bad than a naughty spanking for not wanting to get vaccinated. I had a couple petty charges and probation for graffiti as a minor and shoplifting twice as an adult, a third strike in Florida means actual jail time for me and I don’t think I’d be able to break out so I’ll stick to fantasies.
I’ve only read a few biographies and You Can’t Win is up there with Miles Davis’ Autobiography Miles in terms of entertainment and raw, unapologetic “truth”. I know I’ll come back to both of these books at some point and the audiobooks are both very well done.