The Vanishing Act: What Happened to Jack Black?
In 1926, a book hit the shelves that would become one of the most authentic accounts of criminal life ever written. You Can't Win wasn't penned by a journalist or sociologist—it was the raw, unvarnished autobiography of Jack Black, a man who had spent over two decades as one of America's most accomplished criminals. But here's the mystery: after achieving literary success and apparent redemption, Jack Black simply vanished. What happened to the reformed burglar who captivated readers with his brutal honesty about life in the underworld?
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| The Call (San Francisco). "Two Desperate Criminals Give Finn the Laugh." January 5, 1912: 1 | Public Domain |
From Altar Boy to America's Most Wanted
Jack Black's story reads like a tragic American fable. Born around 1871-1875 (records vary), his descent into crime began with his mother's death when he was just ten years old. After three years in a Catholic convent school, where he served as an altar boy, young Jack's fascination with outlaw stories—particularly the Jesse James saga—planted the seeds of his criminal future.
By age 14, Jack was living largely unsupervised in Kansas City boarding houses, devouring adventure novels by Dumas and Victor Hugo while working at what appeared to be a cigar store but was actually a front for illegal gambling operations. It was here, surrounded by card sharks and dice men, that he absorbed his first lessons in the criminal arts.
His transformation accelerated when he attempted to rescue Julia, a young woman trapped in prostitution. When his father confronted him with the harsh words "John, do you know what you are? You are a pimp" (Black 1926, 62). Jack fled Kansas City and embraced life as a hobo and professional criminal.
The Making of a Master Criminal
What followed was a criminal education that would make him legendary in the underworld. Under the tutelage of mentors like "The Smiler" and the "Sanctimonious Kid," Jack mastered the arts of burglary, safe-cracking, and highway robbery. By his own account, he was on trial for burglary at 20, an expert house burglar by 25, a professional "yegg" (criminal) by 30, and a fugitive highwayman with 25 years in the underworld by 40.
His criminal résumé was extensive: multiple prison sentences, brutal treatment in various penitentiaries, and countless property crimes across the American West. Prison records show he served time in both Folsom and San Quentin, with sentences including eight years for bringing stolen property into California (1898) and twenty-five years for assault to commit robbery and murder (1905).
The California Crime Spree and Newspaper Wars
Even after multiple prison sentences, Jack couldn't stay out of trouble. Following his 1905 conviction for assault to commit robbery and murder (which earned him a 25-year sentence), his criminal record continued to grow. After the 1906 San Francisco earthquake destroyed many court records while his appeal was pending, Jack seized the opportunity and escaped from county jail on January 4, 1912.
The Manhunt
The authorities took his escape seriously. Sheriff Thomas F. Finn immediately issued a detailed wanted poster that painted a vivid portrait of the fugitive: "Age, 42 years; height, 5 feet 9 inches; eyes blue; hair black, gray; complexion, dark sallow; weight, 131 pounds." The poster catalogued his scars like a roadmap of violence—"Long scar across first front right finger, two scars on right side of neck near ear, and one in front of neck on right side; long scar left arm" (Gonzalez 2009, Wanted Poster).
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| Jack Black Photo on 1912 Wanted Poster |
But it was the behavioral description that truly captured the man: "Very nervous and is a drug fiend. Has been in County Jail 7 years. Does not like much hard work. Hangs head when addressed. Likes to gamble and is an expert card player." The poster offered a substantial $200 reward—significant money in 1912—for information leading to his capture or the arrest of those who aided him in his escape (Gonzalez 2009, Wanted Poster Image).
Despite this manhunt, Jack managed to reach Canada, where he was eventually arrested as a pickpocket in Lethbridge under the alias Harry J. King and received a three-month sentence. However, San Francisco police identified and extradited him, leading to a one-year stint in San Quentin on the original charges. Released in October 1913, his freedom was short-lived.
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| San Quentin State Prison | By Zboralski (Own work) | CC BY-SA 3.0 via Wikimedia Commons |
Jack's extensive criminal record was documented with multiple booking numbers: Folsom (1495), San Quentin (26,196), and San Francisco police (16,881, 19,768, 32,193) (Gonzalez 2009, Wanted Poster).
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| Jack Black, Mugshot from San Quentin | By California Department of Corrections | Public Domain |
The Unexpected Transformation
The bridge between Jack Black, the criminal, and Jack Black, the author, was a remarkable man named Fremont Older, a crusading editor of the San Francisco Bulletin. In 1913, Older encountered Jack languishing in Ingleside jail, forgotten by a system overwhelmed by the aftermath of the 1906 earthquake.
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| Fremont Older, 1919 | Public domain, via Wikimedia Commons |
Jack had been convicted of highway robbery before the great fire and sentenced to twenty-five years. His case was on appeal when the earthquake struck, burning all court records. In the chaos of rebuilding San Francisco, Jack's case was simply forgotten. By the time Older found him, Jack had been buried alive in Ingleside jail for seven years with no hope and little faith that his appeal would ever be resolved.
But Older saw something different in this broken man. Unlike other prisoners Older had encountered, Jack was "in a class by himself." There was an intelligence, a depth of character that intrigued the reform-minded editor. Older began working to secure Jack's freedom, setting in motion a transformation that would be as remarkable as any in American criminal history (Older 1926, 316).
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| Fremont Older |
When Jack was finally released, Older didn't just set him free—he gave him a job at the Bulletin and became his mentor, protector, and friend. It was under Older's guidance that Jack began to channel his experiences into something constructive: the raw, honest account that would become You Can't Win.
From Bodyguard to Circulation Manager
Jack's work at the San Francisco Bulletin went far beyond writing. He became "something of a bodyguard to Older, who needed one because his paper continued to fearlessly take on the system." Older didn't stop at exposing lower-level corruption; he was willing to go after "the magnates and their corporations—in this era the Southern Pacific Railroad—at the top of the pyramid." These powerful interests fought back with "an impressive arsenal...from legislators and media outlets to squads of detectives, and—for the really dirty work—underworld characters" (Ruhland 2000, 268).
Jack's reputation as a "tough old con and his underworld connections served nicely" in protecting Older, who "narrowly escaped kidnappers and would-be assassins several times." Later, Jack became the Bulletin's head of circulation during its fierce rivalry with the San Francisco Call in 1916—"a circulation war so serious it involved actual street battles between the two papers' 'newsboys'" (Ruhland 2000, 268).
The Shooting and Its Aftermath
By 1916, Jack had become embroiled in San Francisco's violent "circulation wars" between competing newspapers. He was arrested for slugging Thomas Rockwell, a Call newsboy at Market and Post streets, and later for impersonating a federal officer to spy on The Call's subscription lists (San Francisco Call 1916).
In one of these violent skirmishes, "Robert Wall, a Call newsboy, shot Black, who was wounded so badly that at first he was not expected to survive" (Ruhland, "Afterword," 268). When Jack recovered enough for Wall to be brought to his bedside for identification, "Jack socked him but didn't say a word." Yet within days, in a remarkable display of the redemption that had transformed him, Jack forgave his would-be killer (Ruhland 2000, 268).
The Publishing Triumph
In 1926, Jack Black's transformation reached its pinnacle when Macmillan in New York published You Can't Win. The book was an immediate sensation. What had begun as a serialized cautionary tale in Fremont Older's San Francisco Bulletin—originally titled "Breaking the Shackles"—proved so popular with readers that a major publisher decided to take a chance on the full memoir.
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| First-edition cover of You Can't Win (book) by Jack Black (1926) | By Macmillan Company | Public domain via Wikimedia Commons | |
The gamble paid off spectacularly. You Can't Win became a bestseller and went through five additional printings, a remarkable achievement for any book, let alone the autobiography of a career criminal. The success transformed Jack from "one-man San Francisco reign of terror" into a legitimate literary figure and sought-after public speaker (Ruhland 2000, 265).
Critics and intellectuals embraced the book with surprising enthusiasm. Carl Sandburg praised it, writing, "Much of this book is about loneliness." John Dewey and Lincoln Steffens also endorsed it, recognizing its unflinching honesty and social insights. The book's success suggested that American readers were hungry for authentic accounts of life outside respectable society—stories that revealed the harsh realities behind the country's promises of opportunity and justice (Kennedy 2017).
The Unlikely Collaboration
The hardened criminal became a bestselling author, but some believe Jack Black may not have written "You Can't Win" alone. In one of history's most unlikely literary partnerships, compelling evidence suggests he worked with Rose Wilder Lane, daughter of Laura Ingalls Wilder and the woman who helped craft America's most beloved frontier stories, the Little House on the Prairie series.
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| Rose Wilder Lane | Public Domain via Wikimedia Commons |
The Documented Connection
The relationship between Black and Lane is well-established through their earlier work together. In 1917, nearly a decade before You Can't Win was published, Lane collaborated with Black on two newspaper serials for Fremont Older's San Francisco Bulletin: "The Big Break at Folsom" and "Out of Prison." These prison narratives, published when Lane was working as a writer for Older's paper, may have served as a kind of rehearsal for the full memoir that would follow (National Archives 2000).
Lane was already known as a skilled ghostwriter and collaborator, most famously with her own mother on the Little House books, where correspondence reveals her deep involvement in shaping those iconic American stories. Her experience with frontier narratives and her proven ability to help authors find their voice made her an ideal partner for Black's memoir of the underworld.
Expert Opinion
The case for Lane's involvement in You Can't Win has found support from an unlikely but authoritative source: James Grauerholz, who was William S. Burroughs' companion for 23 years and executor of his estate. As "a longtime student of Black's life and works," Grauerholz has stated that he "strongly suspects that Lane had a hand in the composition of You Can't Win." He also suggests the book is "about 25 percent fanciful," which doesn't diminish its power but acknowledges the collaborative craft that went into shaping Black's raw experiences into the compelling narrative (Grauerholz 2014).
The Burroughs Connection
The book's lasting influence can be traced through another famous reader: William S. Burroughs, the Beat generation author who discovered You Can't Win as a boy in St. Louis and called it his "good red book" (referring to its flame-red boards). Burroughs later used it as the foundation for his first novel Junkie, filling his work with addicts and outcasts united by a code of outlaw honor much like the one Black describes. Bob Dylan seemed to pick up this same ethic in "Absolutely Sweet Marie": "to live outside the law you must be honest" (Kennedy 2017).
The Perfect Mismatch
The contrast between Lane's wholesome frontier stories and Black's gritty criminal memoir couldn't be starker, yet this unlikely pairing may have been precisely what made You Can't Win so powerful. Lane's skill at finding the humanity and moral lessons in harsh frontier life would have been perfectly suited to helping Black transform his brutal experiences into a story of redemption and hard-won wisdom.
A Legacy in Language
Beyond its literary merits, You Can't Win served as a bridge between the underworld and mainstream America, introducing readers to a rich vocabulary of criminal slang that would eventually enter common usage. Black meticulously explained terms like "junk," "stones," "poke," "yegg," "vag," and "plant," along with colorful criminal nicknames like "The Sanctimonious Kid," "Salt Chunk Mary," and "Foot-and-a-Half George" (Teale 2017).
Perhaps most remarkably, Black revealed the criminal origins of phrases that had already crept into everyday speech. The common expression "I have him pegged," he explained, came from thieves' practice of placing wooden pegs in door jambs to determine if a building had been entered during the night—having someone "pegged" meant understanding their patterns and vulnerabilities (Teale 2017).
The Continuing Collaboration
Following the success of You Can't Win, Black became a sought-after speaker and writer on prison reform (Ruhland 2000). He penned articles for Harper's Magazine, including the brilliant 1930 essay "A Burglar Looks at Laws and Codes," which argued that the criminal's code of conduct was often more honest and reliable than the "complicated, perverted, prostituted" legal system of respectable society (Black 1930).
Black also tried his hand at playwriting, working with co-author Bessie Beatty on "Jamboree"—a dramatization of You Can't Win that was first produced in Los Angeles under the title "Salt Chunk Mary" (Kennedy 2017). The play featured characters "drawn from the personal experiences of Jack Black during his years as a criminal or as a prisoner," with the central character being Salt Chunk Mary, a Pocatello madame who runs a "thieves' den and liquor saloon" but has "a 14-karat heart." For a brief time, MGM even paid him $150 a week to write prison dramas, though none of these projects achieved the lasting impact of his memoir (Ruhland 2000, 269; Time Magazine, December 5, 1932).
The Vanishing
And then... nothing.
After the publication of You Can't Win, Jack Black effectively disappeared from the historical record. However, research by Michael Disend and Bruno Ruhland reveals that his final years were far more dramatic than a simple transition from literary success to quiet retirement.
The Decline Begins
Despite the book's popularity, Jack's finances remained precarious. As the Great Depression deepened, his speaking engagements dwindled and royalties from You Can't Win dried up. By the early 1930s, he was trapped in New York, surviving on increasingly rare lecture fees that were, as he wrote to his friend Fremont Older, "keeping him out of the soup kitchens and breadlines" (Ruhland 2000, 272).
Jack knew he was always welcome at Older's ranch south of San Francisco, where he had actually written You Can't Win. Older, legendary for his generosity and considering Jack a great friend, would have gladly helped. But Jack's fierce pride wouldn't let him ask for charity. "I'm not borrowing money," he reportedly told a friend. "I'm afraid I'll never be able to pay it back" (Ruhland 2000, 272).
The Final Plan
In a chilling bit of foreshadowing, Jack had once told his friends exactly what he would do if life became unbearable: he would tie weights to his feet, row out into New York Harbor, and drop overboard. In You Can't Win, Black describes this state of mind as being "ready for the river" (Black 1926, 217). It was a plan both methodical and dramatic—fitting for a man who had lived his entire life on the edge (Ruhland 2000, 272).
The Last Trace
In 1932, Jack Black vanished from New York. Investigators found his watch, pledged for eight dollars in a Manhattan pawnshop, as the only clue to his fate. This wasn't just any timepiece—it was his most cherished possession, a gift from an ex-convict whose life he had helped turn around. For those who knew Jack, finding this watch in a pawnshop was definitive proof he was gone (Ruhland 2000, 272).
Older's wife, Cora, who admired Black, later wrote that her husband believed "Jack did what he always said any down-and-outer should do, 'fill his pockets with rocks and take a header into the bay'" (Kennedy 2017). The image is both tragic and oddly fitting for a man who had always lived on his own terms.
As Randy Kennedy reflected decades later: "Occasionally when I'm on the subway crossing the Manhattan Bridge, I look at New York Harbor and think of Black out there late at night in a little rowboat, wearing his last good suit and taking himself far enough from shore to guarantee no possibility of return" (Kennedy 2017).
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| New York Harbor | By piercarloabate | Pixabay.com | CC0 Public Domain |
The watch represented everything Jack had become: a bridge between the underworld and respectable society, a symbol of redemption and second chances. That he would part with it for a mere eight dollars suggested desperation so profound that death seemed preferable to life.
Questions Remain
Did Jack carry out his dark plan, weighing himself down in New York Harbor? The evidence suggests he did, but questions linger. Was it suicide, or did old enemies finally catch up with the master criminal turned reformer? Did the Depression's grip prove too much for a man who had survived decades in the underworld but couldn't navigate the legitimate world's economic collapse?
Or perhaps the master of disguises and false identities pulled off one final disappearing act like , shedding Jack Black's identity like an old coat and vanishing into anonymity.
A Legacy in the Shadows
The mystery of Jack Black's disappearance remains unsolved, a fitting end perhaps for a man who spent his life in the shadows. His book endures as one of the most authentic accounts of criminal life ever written, a testament to the possibility of redemption and the power of brutal honesty about the darkest corners of the human experience.
But the man himself? Jack Black achieved in death what he could never quite manage in life: he became truly invisible, leaving behind only questions, a pawned watch, and the enduring mystery of what really happened to America's most famous reformed criminal.
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Pinpointing Jack Black's Birth Year
Jack Black's birth year is difficult to pinpoint due to conflicting contemporary records. In 1904, the San Francisco Call reported he was 30 years old, suggesting a birth year around 1874. However, a 1912 official wanted poster listed his age as 42 (birth circa 1870), while in 1915 he told police he was 40 and born in Canada (birth circa 1875). These discrepancies—spanning a five-year range from 1870 to 1875—likely reflect either inconsistent record-keeping or Black's own misrepresentation of his age to authorities, a common practice among transients of that era. Given the clustering of evidence around the early-to-mid 1870s, with the 1904 report placing him at 30 and the official 1912 document being the most detailed, his birth was most likely in the early 1870s.
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