Book Review: You Can’t Win by Jack Black

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Star Ratings for Nonfiction

Writing: *****  (5 stars)

Narrative: **** (4 stars)

Interesting Subject: ***** (5 stars)

Objectivity and research: **** (4 stars. This is a memoir.)

Overall: ***** (5 stars)

Age range recommendation: 14 and up.

The gents at my favorite coffee shop are on a roll with the book recommendations, lately.  You Can’t Win was described to me as “the memoir of a hobo turned safe-cracker turned house burglar turned highwayman turned librarian.”  You can probably imagine that I nearly dropped my maple spice coffee (yum) in eagerness to get my hands on a copy.  I ordered one the moment I got back to work, and have ordered another since to give as a gift.  It was just that good.  I want to call the book “inspiring,” but it’s probably a bad idea to immortalize one’s admiration for such a practiced criminal as Mr. Black on the internet.  So let’s just call it a riveting story, told with level-headed clarity and enough rollicking anecdotes to turn Jack Black’s life into a series of adventures well worth re-telling.

America in the early 20th century was a wild and crazy place. Saloons and opium dens were everywhere, housing wayward women and desperate men; bad men; or pretty much any other crooked variety of fella. Prisons were uniformly horrifying – even more so than they are today – and reforms had only just started. People still carried gold money on horseback. And security measures for houses and trains weren’t quite up to snuff. The West, especially, was paradise for train-hoppers; hobos; “yeggs”; stick-up men; gamblers… any manner of folk who made their living going against the law.

Jack Black (an alias, I believe) didn’t start out as a criminal. His story begins with a quite loving description of childhood years at a Christian school. Right off the bat, he ruminates on the lack of a mother in his life, though his portrayal of the nuns who took care of him shows that there was no lack of decent adult influence in his upbringing.

“It has often been a question with me just how much the best of it a boy has, who has his mother with him until his feet are well planted under him; who has a home and influences until he gathers some kind of a working philosophy that helps him to face the world… Looking back at it, it seems to me that I was blown here and there like a dead leaf whipped about but 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 way than the gentle, saintly woman who taught me my prayers in the convent.”

Jack’s father, too, is described with respect and care. In fact, I was touched by how Mr. Black’s protective nature towards his father’s reputation and feelings only grew throughout his life of crime, which is why it’s not hard to sympathize with the distance he keeps between them in later, more adventurous, years. Even as a kid, his knack for business and shrewd observational skills get Jack into troublesome learning experiences.

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

Well, it won’t be long before travel and adventure fill Jack’s days, though misery is always snapping at his heels. (As for romance… you won’t find much of it in You Can’t Win. One of many reasons I loved the book.) His first arrest is a classic case of being in the wrong place at the wrong time. Subsequent incarcerations are the unhappy results of more purposeful ventures. Jack Black writes candidly about his resilience in crime, neither apologizing for his misdeeds nor whining openly about the hard life of a roving thief.

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.”

Black’s unabashed memoirs are told in a fairly linear fashion, though every now and then he’ll mention the untimely demise of a fellow “yegg,” or write ominously about a future mistake as yet unknown to his younger self during the exploit of the moment. Most cases of foreshadowing lead to reciprocal and gratifying anecdotes later on in the narrative. Jack Black is a good writer: trust that he will reveal the conclusions of any and all story-lines that conclude neatly enough.

Characters – real people, yes, but certainly their colorful personalities deserve the term – filter in and out of his acquaintance as fate (or the judiciary system) lead their paths together and astray. From the first time he witnesses a fellow train-hopper get squashed by the cargo, through partnerships with the likes of “Smiler;” “Foot-and-a-Half George;” and “The Sanctimonious Kid,” Jack is a diligent observer of the attitudes that best suit a man on the road. Charming criminals, hardened ladies who orchestrate connections in crime, and even leaders of bloody prison break-outs take Jack into their confidence quickly and easily. I think that his quiet, unassuming nature serves him well in the field. Reading his recollections has made me want to write careful descriptions of the people I encounter: their mannerisms, their ways of speech, and even the measure of their moral standing. You never know when they might turn up in your life again, fifteen years later, harboring a grudge or willing to spring you from behind bars. Bums and highwaymen tend to have interesting backgrounds of their own accord, but it takes a memory like Mr. Black’s and a simple-but-crystallized handle of the English language to give such individuals real life on the printed page.

His voice never falters into sentimentality or veers towards the arrogance of a man who has succeeded where others have not. Sometimes he needs help, and he is grateful when he gets it. Sometimes he has the chance to assist a fellow disreputable soul, and he does so without expecting congratulations. There were runs of bad luck which made me cringe at the injustice of it all – a real life of crime has no guarantee of satisfaction at the end of several months’ plotting, despite what novels and films would have us believe. But there are still moments of triumph and even unexpected kindness to keep his mind in the game for so many years.

The era of saloon shoot-outs, railroad heists, and sacks of gold has dwindled into our less-thrilling modern age of electronic money and biometrics. I probably wouldn’t like to go through my days in a hail of bullets and a succession of jail cells, but it was awfully fun to read Jack Black’s account of such a life. His subdued good humor and unusually merciful view of human nature have rubbed off on me a little bit. If more “good” people adopted an attitude like this one “bad” man, I think we would all have a better idea of how luck and life all even out in the end.

“A bleak background! Crowded with robberies, burglaries, and thefts too numerous to recall. All manner of crimes against property. Arrests, trials, acquittals, convictions, escapes. Penitentiaries! I see in the background four of them. County jails, workhouses, city prisons, Mounted Police barracks, dungeons, solitary confinement, bread and water, hanging up, brutal floggings, and murderous straitjacket.

“I see hop joints, wine dumps, thieves’ resorts, and beggars’ hangouts.

“Crime followed by swift retribution in one form or another…

“In those twenty-five years I took all these things, and I am going to write about them.

“And I am going to write about them as I took them –with a smile.”

(Here’s another good review of the book, which helped inspire me to buy it sight unseen.)

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