Book//mark – You Can’t Win | Jack Black, 1926

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Jack Black (1871-1932)                                               Jack Black, You Can’t Win, 1926


“I was wrong. I knew I was wrong, and yet I persisted. If that is possible of any explanation
it is this: From the day I left my father my lines had been cast, or I cast them myself, among
crooked people. I had not spent one hour in the company of an honest person. I had lived in
an atmosphere of larceny, theft, crime. 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 you live with wolves, you will learn to howl.”

“I’m going to write about them as I took them — with a smile.”

“There were times when I thought I got a bit more punishment than was coming to me,
but I don’t regret a minute of it now. Each of us must be tempered in some fire. Nobody
had more to do with choosing the fire that tempered me than myself, and instead of
finding fault with the fire I give thanks that I had the metal to take the temper
and hold it.”

“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.”

“Every time I stole a dollar I knew I was breaking a law and working a hardship on the
loser. Yet for years I kept on doing it. I wonder how many of us quit wronging others for
the best reason of all — because it is wrong, and we know it.”

“The books so fired me with the desire for travel, adventure, romance,
that I was miserable most of the time.”

“I say they had character because, while they did wrong things,
they always tried to do them in the right way and at the right time.”

“My experience with short rations in many places has convinced me that we would
all be healthier and better nourished if we ate half as much food and chewed it
twice as long.”

“Looking back at it, it seems to me that I was blown here and there like a dead leaf whipped
about by the autumn winds till at last it finds lodgment in some cozy fence corner. When I left
school at fourteen I was as unsophisticated as a boy could be; I knew no more of the world
and its strange ways than the gentle, saintly woman who taught me my prayers in the convent.
Before me twentieth birthday I was on the docket of criminal court, on trial for burglary.”

Jack Black, You Can’t Win, 1926

John Black was a late 19th century/early 20th century hobo and professional burglar, living
out the dying age of the Wild West. He wrote You Can’t Win (Macmillan, 1926) a memoir or
sketched autobiography describing his days on the road and life as an outlaw. Black’s book was
written as an anti-crime book urging criminals to go straight but is also his statement of belief
in the futility of prisons and the criminal justice system, hence the title of the book. Jack Black
was writing from experience, having spent thirty years (fifteen of which were spent in various
prisons) as a traveling criminal and offers tales of being a cross-country stick-up man, home
burglar, petty thief, and opium fiend.

Black had spent a long time planning the job and was extremely depressed when it failed, not
to mention virtually broke. A friend offered him a “straight” job washing dishes to tide him
over, but Black refused, explaining his philosophy of life as follows:

“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 is an essentially anonymous figure (even his actual name is uncertain) who is
recognized through association with William S. Burroughs. Although his philosophy on
life was especially influential to Burroughs, who associated with similar characters in his
early adulthood and mirrored the style of You Can’t Win with his first published book, Junkie,
Black’s writings also had a profound effect on the writings and lives of all the Beat Generation.
In his foreword to the 1988 edition of You Can’t Win (reproduced in a 2000 edition), Burroughs wrote:
“I first read You Can’t Win in 1926, in an edition bound in red cardboard. Stultified and confined 
by middle-class St. Louis mores, I was fascinated by this glimpse of an underworld of seedy 
rooming houses, pool parlors, cat houses and opium dens, of bull pens and cat burglars and 
hobo jungles. I learned about the Johnson Family of good bums and thieves, with a code of 
conduct that made more sense to me than the arbitrary, hypocritical rules that were taken for 
granted as being ‘right’ by my peers.”
After his last spell in prison Jack Black became friends with wealthy patron Fremont Older and
worked for Older’s newspaper The San Francisco Call. He worked on his autobiography with
Rose Wilder Lane and eventually composed essays and lectured throughout the country
on prison reform.

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