The Identity of The Sanctimonious Kid

Exploring the historic background of Jack Black's 'You Can't Win', and investigating the identity of The Sanctimonious Kid.
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Spoilers Ahead!

This article is about Jack Black's autobiography You Can't Win. Needless to say, this contains spoilers. If you want to enjoy the book to its fullest —and I recommend you do so, it's an amazing book— read it first, and come back later.

Having said this, Black reveals the ultimate fates of his friends to the reader almost as quickly as he reveals their existence. So even if you read on in spite of my prior warning, I wouldn't be spoiling too much.

Throughout the article I'll be quoting from the AK Press edition, which is freely available on archive.org


Among my many guilty pleasures is rereading my favourite books, and Jack Black's acclaimed autobiography You Can't Win is one I've returned to again and again. The AK Press edition —with an introduction by William S Burroughs— sits dog-earned on my bookshelf, well-worn from many nights spent buried in its pages. Once I picked it up I couldn't put it down. Black's prose is direct, matter-of-fact, and at the same time wonderfully poetic. He writes of his darkest days with grace and good humour, and takes the audience along with him for the adventure of a lifetime.

Jack Black, San Quentin mugshot, 1912.

You Can't Win features a cast of extraordinary, colourful characters that Black's words paint so vividly. Full of charm and life, they leap out of the page and run wild in the reader's imagination. Of all the gallery of rogues that grace the pages of You Can't Win, perhaps none remains more intriguing than The Sanctimonious Kid.

'Sanc' is first introduced to the audience as an esteemed member of the 'Johnson Family' criminal gang, with whom Black becomes acquainted while serving a prison sentence in Salt Lake City. Due to his reputation as an honest criminal, Black is 'put in' with 'the right people'. The right people in this case being Foot-and-a-half George, a safe-cracking Civil War veteran; Soldier Johnnie, an experienced bank-robber; and The Sanctimonious Kid.

"Sanc" had everything that George lacked. Tall, six feet, slender and soft stepping, more active than most men half his size, you would not suspect him of two hundred pounds, solid flesh and bone. Straight without stiffness, natural, like an Indian. Dark hair, eyes and skin. Handsome, intelligent. Years after, I saw him in the dock of a crowded court room in a big city. His head was the finest, his face the handsomest, and his poise the surest of any there, from the judge down to the alternate juror. His nose, eyes and forehead might have been those of a minister or divinity student. But there was a hard look about his mouth, and something in his jaw that suggested the butcher. He was educated and a constant reader. Whether it was his appearance or his careful manner of speech that got him his monoger, "The Sanctimonious Kid," I never knew. He was serving a short sentence for house burglary, at which he was an expert. The Sanctimonious Kid, You can't Win, Page 97

The esteem with which Black held The Sanctimonious Kid is clear. Throughout the book, Sanc is portrayed as streetwise and intellectual, as capable of great introspect as he was savage violence.

"Kid," he said later, "this is the season of peace on earth and good will to men. Who gives to the poor lends to the Lord, but when I give anything to the poor I am going to have a better motive. However, we are not givers; we are takers, and our taking should be reasoned out rationally. We will reverse this 'giving and lending.' We will rob the rich and discomfit the devil; thereby, perhaps, finding favor in the sight of the Lord." The Sanctimonious Kid, You can't Win, Page 145
"…The smallest trifle will upset you, and you'll have leisure to repent your carelessness. When you get your new suit from the tailor's, take all the tags out of it, and when you buy a hat don't let the hatter stamp your name on the sweatband. You don't know what house you might lose it in. "I know thieves so conceited and foolish that they have their names in their hats and monogrammed pocket handkerchiefs, and neat little notebooks with all their friends' addresses and phone numbers carefully noted. That's the type of thief that calls the police 'a bunch of chumps,' and goes to jail crying, 'Somebody snitched.' The Sanctimonious Kid, You can't Win, Page 126

It's easy to see how Black's tales of riding the rails over a wild and untamed American heartland with The Sanctimonious Kid were so influential on the beat poets. But is there more to the story? A lot has been written about Black's wild, real-life exploits outside You Can't Win, but what of The Sanctimonious Kid? If he did indeed escape from Canon City prison, and eventually end up in Australia, then surely he must have left some mark on the world that can be traced, some thread that can be followed to tease out the truth… In this article I intend to do just that, and maybe discover the identity of The Sanctimonious Kid.

Escape from Canon City

By far the most interesting lead to follow is Black's claim that the Sanctimonious Kid escaped from Canon City prison.

"A year after we were banished from Pocatello a letter from Mary told us that the Sanctimonious Kid was arrested in Denver, charged with a tough burglary, and wanted help… I sneaked into Pocatello for her generous contribution, and with what we could spare we went to Denver and got him the best lawyer there —Tom Patterson, afterward Senator Patterson from Colorado. We stayed in the state, turning every dollar we could steal into his lawyer's office, but in vain. Sanc got everything Patterson had in the way of service, and finished with fifteen years at Canon City." You can't Win, Page 168

The Canon City Black refers to was none other than the Colorado State Penitentiary, located in Cañon City, Colorado. Better known today as the Colorado Territorial Correctional Facility. The Senator Patterson mentioned is Thomas M. Patterson, who was indeed elected to the United States Senate in 1901.

A historic view of the Colorado State Penitentiary. Picture courtesy of Denver Public Library Special Collections.

After George's death, Black travelled from Utah to Chicago. While there he visited the historic World's Fair, which took place in 1893. Since Sanc was sentenced to 15 years in Canon City while George1 was still alive, we know that Sanc's incarceration occurred no later than that date.

We traveled together for several years after he was released, and I found him one of the squarest and most resourceful thieves I ever knew. At last, after one of the cleverest prison escapes on record, he went to Australia where he was hanged for the murder of a police constable. You can't Win, Page 98

The Colorado State Penitentiary played host to many escapes over its long history, but none more interesting than the January 22, 1900 breakout of prisoners Thomas Reynolds, Charles E. Wagoner, Kid Wallace, and the already infamous child criminal Anton Woode.

On that cold winter night the four inmates staged a daring and violent escape from 'Canon City' that would make headlines. Assigned the evening shift in the prison's boiler room, the inmates took the night guards by surprise as they returned from their evening meal, mortally wounding Night Captain William C. Rooney in the process. The four then sabotaged the prison's electrical system by pouring soapy water into the belts that fed the boiler, and escaped over the walls in the ensuing blackout (Harmon, 2011).

Fleeing into the frigid January night, they split into pairs to throw authorities off their trail. Wallace and Woode headed north, while Reynolds and Wagoner headed eastwards towards the nearby town of Florence. Wallace and Woode would ultimately be recaptured three days later in the town of Victor, some 30 miles away, and were promptly returned to prison where they were given what Warden C.P. Hoyt called 'The dungeon treatment' for their efforts. Police would catch up to Reynolds two days later in Florence, where he and Wagoner had taken warm clothes and food from a local household before going to ground with the law hot on their heels. After a brief chase Reynolds would be apprehended by the authorities. Wagoner however managed to elude his pursuers, presumably having hitched a ride on a train bound for Peublo ("How Reynolds Was Taken", 1900).

The elusive Wagoner had managed to slip away for good2. Despite an impressive reward of $1000 offered for his recapture, Wagoner would remain free ("Governor Thinks Wagoner Was Frozen To Death", 1900). Reynolds however, would not be so lucky. He was captured by a mob of angry townsfolk on his way back to prison, and lynched in retribution for the murder of Captain Rooney (Wermer, 2006).

The stone walls of the Colorado State Penitentiary.
Picture courtesy of Denver Public Library Special Collections.

Charles Evans Wagoner, Criminal

Prisoner 2998 Charles Evans, 1889.
Picture courtesy of Colorado State Archives.

Colorado State Penitentiary prisoner 4580 Charles E. Wagoner's final stay in Canon City began on August 11, 1898, sentenced to five years for robbery and burglary. Wagoner was a career criminal who had been jailed twice before in Colorado3 under the name Charles Evans, prisoner number 2003 and 2998. Once in 1889 for stealing a horse at Dodge City, and again in 1892 for a burglary he'd committed several years earlier ("Convict Hunt Abandoned", 1900; "Criminal Court", 1889; "Court Briefs", 1892). Wagoner had already attempted to escape Canon City in 1899, however he was recaptured an hour later.

The Rocky Mountain Daily News describes Wagoner as a skilled plumber4: 'in that population of 544, there was only one plumber and man accustomed to handling pipes. This was Wagoner'. It was this skill that led him —in spite of his poor reputation— to be entrusted with carrying out urgent repairs in the prison's boiler ("Warden Hoyt Was Not Obeyed", 1900).

Official prison records recorded Wagoner as being 5'8 1/2" in height, of dark complexion, and with a conspicuous birthmark on his neck5. The contemporary article Mutiny and Murder in Prison in the Pueblo Chieftain newspaper describes Wagoner as '34 years old, and about 6 feet in height and of a dark complexion', which is in line with Black's introductory description of being: 'Tall, six feet, slender and soft stepping, more active than most men half his size, you would not suspect him of two hundred pounds, solid flesh and bone… Dark hair, eyes and skin. Handsome, intelligent'.

While Wagoner's prison sentences don't quite match up with Black's account, if Wagoner were indeed The Sanctimonious Kid, it's possible that Black took artistic licence with the details.

Charles Schayne?

Prisoner 3157 Charles Schayne, 1893.
Picture courtesy of Colorado State Archives.

Another potential candidate for being The Sanctimonious Kid is the mysterious Charles Schayne, an ostensibly experienced burglar sentenced to four years at Canon City in February 1893 ("Quick Conviction of a Burglar", 1893). Schayne, prisoner number 3157 wouldn't stay put for long. On April 1st of that year, he embarked on a truly daring, and evidently successful, escape by cutting a hole in the roof of his cell —situated on the prison's upper floor— and climbing down using a makeshift rope fashioned from a blanket. According to newspaper reports, he then fastened an iron hook to his blanket rope, and used it to scale the outer walls, from which he dropped down the other side to freedom ("Prisoner Scales the Well Lighted Walls of Canon's Great Jail", 1893). Despite having a much more distinct name to search for, I can't seem to find anything else about Schayne in historic newspaper clippings6. He's described as six feet tall, and 30 years of age, which tracks perfectly with Black's description of The Sanctimonious Kid. His daring escape also tracks with Black's account of Sanc having made 'one of the cleverest prison escapes on record'.

Others Clues?

Other Escapees

As best I can tell, around half a dozen people successfully escaped Canon City around the time of You Can't Win. Nearly all can be conclusively ruled out as having been The Sanctimonious Kid by some fact or another. There's certainly a wealth of interesting stories to be told, but unfortunately I can't find any that really fit the details of Black's autobiography.

The Thomas M. Patterson Connection

Black's account that Sanc had Thomas M. Patterson as his legal counsel connection seems like a promising lead to follow, but unfortunately I haven't been able to follow it anywhere. I've pored over hundreds of articles at the amazing Colorado Historic Newspapers Collection, looking for some record of Patterson defending a thief of Sanc's description, but I couldn't find anything useful.

The University of Colorado Boulder maintains the Thomas M. Patterson Family Papers, but these don't seem to include the records of his legal practice. I would guess at this point these records have long since been lost to time.

Thomas M. Patterson purchased the Rocky Mountain Daily News in 1890, so it's unlikely he was practicing law after this point. If Sanc was indeed defended by Patterson, his conviction was likely before this date.


"We were comparing notes for a week. It was from him I learned that the Sanctimonious Kid had escaped from Canon City before finishing his fifteen years and that he had gone to Australia, where he was hanged for killing a police constable." You can't Win, Page 301

Australia is a young country, even by the standards of other young countries like America. It has few major cities, even fewer states, and in the fashion of the Commonwealth, good record keeping. Compared to its fellow Anglophone countries, Australia executed comparatively few prisoners, and executed even fewer for the murder of police officers. If The Sanctimonious Kid was indeed hanged in Australia for such a crime, it shouldn't be very hard to identify him.

On Christmas Eve of 1912, Black was sentenced to a year in San Francisco's San Quentin prison for a 1904 charge of assault to commit robbery ("Robber Is Resentenced After Long Legal Fight", 1912). This would ultimately be his final time behind bars. It was during this sentence that he learned from Soldier Johnnie of Sanc's fate in Australia. If Black's account is to be taken at face value, it would mean that Sanc's execution took place no later than 1912.

The Australian Police maintain a memorial in Australia's capital city of Canberra to honour police officers who have lost their lives in the line of duty. The National Police Memorial website maintains a comprehensive list of all the officers honoured by the memorial, stretching all the way back to the sensational death of Constable Joseph Luker, in 1803. Reading every record from 1893 through 1912, it's possible to conclusively rule out every one of the known perpetrators as having been The Sanctimonious Kid:

The Truth?

Was Wagoner The Sanctimonious Kid? Possibly. The mysterious character of Wagoner certainly fits the description: An educated and ruthless burglar. Determined, violent and unrepentant. If nothing else, the criminal convictions recorded against him definitely resemble the predilections of the Sanctimonious Kid.

But was Sanc hanged in Australia? I'm not convinced. Everyone executed for killing a policeman in Australia during the period Sanc could possibly have been there can be sufficiently ruled out. Is it possible that Sanc was actually executed for someone else's murder? Sure, but even then there aren't many good leads to follow. Maybe The Sanctimonious Kid was still pursued, and Black fabricated the story of his escape to Australia to throw the authorities off his trail? Maybe Soldier Johnnie was misinformed? Unfortunately, I don't think we'll ever know.

It's possible that Black constructed his tales and characters from contemporary criminal folklore. News at the turn of the 20th century may not have travelled as fast as it does today, but Black could definitely have read about Wagoner's daring escape into the Colorado night, and fabricated his own connection to the story7. Perhaps the story of Wagoner's escape propagated itself far and wide, travelling along the rails as Wagoner himself was rumoured to have escaped, a legend told over campfires in the hobo jungles of the American heartland.

In a fantastic blog post, Jon Von Zelovitz points out that while Black may have elected to spare his readers the gorier details of his life of crime, the reporters covering the police blotter for the San Francisco Call didn't pass up the chance to thrill their readers with tales of Black's daring and violent capers. Contemporary newspapers not only lend considerable authenticity to Black's autobiographical claims, they also hint that perhaps Black's real-life exploits were even more extraordinary than his account suggests.

While it's clear that some degree of artistic license has been taken in his telling, I choose to regard Black's characters as having represented real people. If for no other reason than the great, solemn affection with which they are regarded in the telling of his story. Black's statement that he honoured his father by never putting his family name in a legal document hints that he may have had his own peculiar reasons for obscuring the identity of his subjects.

One is surely tempted to mourn the passing of Foot-and-a-half George, Sanc, and Soldier Johnnie, as —how Black himself put so solemnly— 'unwept', and 'unhonoured'. However reserved for them is the honour of living on indefinitely; Captured forever in the hearts of readers captivated by the exploits of these outlaws, who rode the rails in search of adventure in a wild and free age long since lost. Almost a century on, these tales of daring in a time fortunes were won and lost by the bold still manage to captivate the imaginations of readers everywhere.

Whatever the true names of these men, and wherever their final resting places may be, their spirits will live on to capture the hearts and imaginations of readers for many years to come.

Further Research: If you're researching You Can't Win yourself, and have any information you could add to this article, I'd love to hear from you! If you think the truth is still out there, and would like to take up the task of researching this topic for yourself, I'd be happy to share my notes with you.


  1. I looked into whether there was any record of Gold Tooth's murder in the papers. I could only find two clippings in the Library of Congress about unsolved homicides in Pocatello that were around the right time: A Foul Murder In Idaho in the Butte semi-weekly miner, and A Murder At Pocatello in The Salt Lake herald. Neither of which really matches the details of the story, but who knows what actually happened around that campfire? As George himself said:

    "…No matter what they say, dead men do tell tales. Robbery and burglary are soon forgotten and outlawed, but when you leave a dead man behind you they've got the balance of your life to catch you and hang you. A couple of those bums could go into the Salvation Army ten years from now and get religion and hang me." Foot-and-a-half George, You can't Win, Page 170

    I also looked for any record of George's death in the Utah newspapers in the Library of Congress' Chronicling America collection, from around 1889 to 1903, but couldn't find anything that matches Black's account. Black explicitly mentions reading about it in the papers, presumably in Provo, but unfortunately I can't find any record of that now.

  2. I can't find any credible evidence that Wagoner was ever recaptured. Several contemporary newspaper clippings claim he was recaptured, however other more recent and significant articles contradict this claim. Whether Wagoner had been smuggled back into the jail to avoid a waiting lynch mob was also a matter of serious conjecture.

    Some contemporary articles feature lurid claims of Wagoner terrorising the Colorado hinterlands, however I don't personally consider these credible.

    I consider the articles Convict Hunt Abandoned, Tired Of Chasing Rumours, and Noted Convict Once Member of Band Which Dynamited Gate at Canon City and Escaped —all from The Rocky Mountain News— to be the authoritative last word on Wagoner.

  3. If, like me, you were wondering why an enterprising criminal would find themselves in Colorado again and again, this map might clear up why. Around 1880 Denver experienced a sudden population boom, and along with it would come plenty of opportunities for crime. This website is another great resource of maps showing America's population density over time.
  4. The Canon City Library's Local History Center lists Wagoner's occupation as 'Engineer'. Black clearly held Sanc in high esteem on account of his intelligence: 'He was educated and a constant reader' (Black, 1926, p. 98).
  5. A feature that would no doubt prove no small hindrance to a professional burglar looking to weave his way through society unnoticed. It would also make it easy to match Wagoner against prisoner records in Australia… If any did exist.
  6. One newspaper article spells his name as Shayne, but this doesn't lead to any new information.
  7. You Can't Win tells the story of a dramatic encounter between Sanc and the notorious 19th century conman Soapy Smith, in which the latter was relieved of a small fortune at gunpoint. Much has been written about the life and crimes of Soapy Smith, whose adventures came to a bloody end in July of 1898, gunned down in a dispute over gambling losses.

    As author Jeff Smith notes in his wonderful blog, it was all-too-common for authors to fabricate tales of Soapy to traffic in his notoriety. While Black's account of the encounter has no provenance, it's plausible enough. For what it's worth, the gambling house in which Black claims they ran their gambling concession —The Chicken Coop— is referenced in this lively piece by John R. Sanders.

    I admit that it's a bit of a stretch to imagine Black reading about Wagoner's escape in 1900, and keeping the story in mind for 26 years just to fabricate his own connection to it. Black could not possibly have imagined the means by which I'm able to research his story today. In my opinion, the fact that his story stands up to as much modern scrutiny as it does is a testament to its veracity.