Jack Black’s “You Can’t Win”: Another Life of Crime
This autobiography of a career criminal is also a fascinating portrait of the American proletarian criminal class and their associates at the end of the 19th century, from hobos hopping trains and being beaten mercilessly by railroad “bulls” to Salt Chunk Mary, an incredible character and the best fence for stolen property in the West. Black pops in and out of jail while continuously improving his connections with a widespread and mutually-supportive underworld. When one is in trouble, friends all pitch in: a socialist model in stark contrast to the prevailing mentality in America.
In passing, he profits from his experiences to provide first-hand social criticism that was surely radical at the time, and still bears up.
I’ve read a number of books of this type; Edward Bunker’s “Education of a Felon” is an interesting comparison. During my reading, I was increasingly disturbed by a nagging doubt: was the book genuine? The lack of documented detail  and Candide-like structure were capped by the classic “exploitation” formula: a final chapter of the form “I hope my story will serve as a warning to stay away from the criminal life.”
Does this make me more of a skeptic (or less gullible) than William S. Burroughs, who cites the book as a key influence? Perhaps. But now we have the Internet. Some searching led me to on-line archives of the San Francisco Call, the newspaper run by Fremont Older, a progressive with faith in the inner goodness of Black who bargained him out of jail and set him on the good path.
I discovered something marvelous. The timidity of Black to set out the gory details of his criminal life did not affect the reporters who covered the police blotter for the SF Call.  Quite the opposite. Here are a few examples that make for entertaining reading, and that also removed any remaining doubts about the authenticity of Black and his adventures. I suppose we have to take into account the vast differences in society and what has become allowable in literature since 1926, but imagine if he had let loose with all the nasty details that even the reporters didn’t know! Whew! What a book that would have been.  (Links below.)
It was not long after Black landed at Ingleside [jail], five years ago, that he became a power within the walls. He set himself as the commercial king and sold the most sought after commodity — “dope.” It is known that when in his cell Black sold “shots” of morphine through the wicket to other prisoners at 10 cents for each hypodermic injection. He would insert the needle in the customer’s arm, inject the “shot” and collect his fee.
San Francisco Call, Volume 111, Number 36, 5 January 1912
Black was the wealthiest man in the county jail, not excepting the officials. He was known as the “king of the opium ring,” and made a small fortune in the sale of morphine and cocaine to the other prisoners who desired the drugs. It is known that several days before his departure he had $2,700 of his own money strapped about his waist in a money belt. Two weeks ago he told a grand Juror who was inquiring into conditions in the jail that his “bank roll” amounted to $2,000. Among his other possessions he had diamonds, unset, solitaire, clustered, and watches and other jewelry. He was abundantly supplied with expensive clothes of the latest fashion.
San Francisco Call, Volume 111, Number 36, 5 January 1912
When the officers attempted to place the suspect under arrest Black drew a revolver. Before he could make use of the weapon, however, the detectives closed in on him. A desperate struggle ensued, and Black was not subdued until beaten almost into insensibility.
San Francisco Call, Volume 95, Number 138, 16 April 1904
A remarkable detail is the prevalence of opium sales and consumption by Chinese people, who seem to have their own separate underground society. In one scene, Black is in an unfamiliar town and needs a hit of “hop” (opium) . He simply looks for a Chinese laundry, in the way that someone today might look for a McDonalds, knowing in advance what is on the menu.
Another recurring theme is corruption in the criminal justice system, and the book finishes with an appeal for its reform. Black repeatedly buys himself out of situations in the most matter-of-fact way. At least today these practices are more concealed.
Overall, an interesting read in spite of my regrets over what this book could have been. Thanks to my friend Phil for recommending it, and to my old neighbors AK Press in SF and Amok in LA for putting it out.
 For example, when he steals a (fake) ruby, he says “strangely, it never made the papers.”
 The book’s excellent Afterword, written by Bruno Ruhland, lifts a phrase from an article without crediting it, while nevertheless citing the wrong date (1906). “Black, in 1904, caused a reign of terror in the Mission district during the course of a number of daring robberies and holdups.” (cf. SF Call 24 December 1912)
 Now I know where the fifties (?) term hop-head came from!
 The catastrophically bad Veridian OCR software for on-line newspapers apparently does not perform even the most elementary heuristic cleanup on the scans, leaving things like numbers and capital letters in the middle of words. It relies on “crowd sourcing” (cf. Wikipedia): the kindness of strangers to come in and fix up the lousy scans. As a public service, I located as many articles as I could about Jack Black and manually corrected them. Example:
A. Kriox, ;a /Valencia Street Gf roceiy ; Identifies ;. Him as ;tlie:Man^hat Held Him Up
-> A. Knox, a Valencia Street Grocer, Identifies Him as the Man That Held Him Up
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