Rare Book Monthly

Articles - December - 2025 Issue

Lost Kerouac Short Story Discovered in Deceased Mafia Boss' Artifacts

A lost, or unknown short story by Jack Kerouac was recently discovered among the artifacts of a Mafia crime boss who died 40 years ago. Too bad Kerouac isn't here to write this story as he could have done it better than anyone. The story comes in the form of a signed typescript Kerouac sent to a friend. He had a habit of doing this as he was as yet an unpublished great novelist who no one but close friends knew was great or even who he was. The date is April 15, 1957, five months before the publication of On The Road. The story's title is The Holy, Beat, and Crazy Next Thing.

 

The backstory is not entirely known. Kerouac gave the story to a San Francisco poet. The part about how the letter ended up in the collection of Mafia boss Paul Castellano is unknown. Castellano succeeded to the boss of the Gambino crime family when Carlo Gambino died in 1976. Gambino died of natural causes. Castellano was not so lucky. The Gambino family broke into factions as the choice of Castellano was not universally popular, but it was accepted as this was Gambino's wish. However, internal struggles continued within the crime family, which eventually led a subgroup headed by John Gotti to decide it was time to off Castellano. He was shot as he entered a restaurant for a supposed meeting. Gotti quickly replaced Castellano as boss. Gotti would die of natural causes in 2002, and remained boss until that time, but the last 10 years of his life were spent in prison. Live by the sword...

 

This still doesn't explain how the story became part of Castellano's collection. That is unknown, other than it remained with his artifacts for another 40 years after he suddenly passed away in 1985. It was finally put up for sale and the story was purchased by Your Own Museum. They in turn put it up for sale for $8,500 and it quickly sold.

 

As for the story, it is not a disappointing amateur piece in want of a lot of editing. Reading it quickly reveals his writing genius, what sets him apart from even very good writers. While a separate piece, it sounds like it could be a missing chapter from On the Road. The parties are the author, “Dean Moriarity,” and “Marylou,” all characters from On the Road. It begins, “We hit Denver with the gas gauge kissing empty and the Hudson coughing dust from a thousand desert miles. It was that wild, holy, and crazy time when Dean and I were inseparable, two halves of a lost and found coin, and Marylou was with us, a sad-eyed angel in a too-tight sweater. The money was gone, spent on gas and cheap wine and a wild night in a Tucson motel that ended with a fistfight and a sprint to the car. Now we are broke, the sky was the colour of a dirty nickel, and a mean mountain wind cut down Larimer Street.”

 

The story concludes with Dean comforting young Marylou who wonders what it is they are doing. Dean replies, “'We're living. That's all. We're just...living. And when you're living, you're digging everything there is to dig, because it's all part of the great, mad, glorious dream.' He put his arm around her, and she leaned into him, a brief tender moment in the long rush.”

 

The story concludes, “We drank until the wine was gone and the stars turned into one smeared light. We talked about everything and nothing, our words tumbling into the vast American night. We were together, on the road, broke and freehand for that one moment, on a nameless hill, under a billion stars, it was everything. It was enough. Then Dean jumped up, 'Okay! Now! Let’s go find Ray Johnson! He’ll be at the poolhall! The night is young!' And the moment was gone, shattered by the next frantic impulse, and we piled back into the car, roaring towards the next thing, always the next thing, the holy, beat, and crazy next thing.”

 

Kerouac was a master at painting a picture with words. An artist. Five months later, we got the whole road trip story and everyone came to know who Jack Kerouac was.

Rare Book Monthly

  • Aste Bolaffi, June 17-18: Galileo Galilei. Dialogo sopra i due massimi sistemi del mondo tolemaico, e copernicano. Firenze, 1632
    Aste Bolaffi, June 17-18: Saverio Manetti. Storia naturale degli uccelli. Firenze, 1771-76
    Aste Bolaffi, June 17-18: Fortunato Depero. Depero futurista. Rovereto, 1927
    Aste Bolaffi, June 17-18: Nicolas Visscher. Atlas minor sive totius orbis terrarum contracta delineat ex conatibus. Amsterdam, circa 1649-95
    Aste Bolaffi, June 17-18: Andreas Vesalius. Anatomia. Addita nunc. Antiquorum Anatome. Venezia, 1604
    Aste Bolaffi, June 17-18: Tristan Tzara and Salvador Dalì. Grains et Issues. Parigi, 1935
  • June 25, 2026
    Doyle, June 25: Houdini's biography, boldly signed. $3,000 to $5,000.
    Doyle, June 25: A volume from Abraham Lincoln's library, signed just before heading to Washington for his inauguration. $20,000 to $30,000.
    Doyle, June 25: A very early Confederate recruiting manual belonging to the chief commissary in Lee's Army. $600 to $800.
    Doyle, June 25: Rare hand-colored lithographs of the life of Napoleon. $20,000 to $30,000.
    Doyle, June 25: The "Holster Atlas" of the American Revolution. $5,000 to $8,000.
    Doyle, June 25: Jewish ceremonies in fine hand-colored engravings. $7,000 to $10,000.
    Doyle, June 25: A very rare work on Turkish military costume. $1,000 to $1,500.
    June 25, 2026
    Doyle, June 25: The most important illustrated work on the Mexican-American War. $10,000 to $15,000.
    Doyle, June 25: The finest illustrated book on Afghanistan. $10,000 to $15,000.
    Doyle, June 25: Henry Justice Ford St. George rescues the Princess from the horrible Dragon. $2,000 to $3,000.
    Doyle, June 25: A rare work of Prussian Army uniforms under Frederick William II, with exquisite hand-colored engravings. $800 to $1,200.
    Doyle, June 25: Lenny Bruce typed letter signed to a Village bohemian during his obscenity trials, with a manuscript note and drawing. $300 to $500.
    Doyle, June 25: Schiff's scarce Shanghai Sketchbook. $300 to $500.
    Doyle, June 25: The first accurate published representation of the American flag. $2,000 to $4,000.
  • Old World Auctions (June 17): Lot 123. Celebrate 250 Years of Independence with Original Stars and Stripes (1790) Est. $1,400 - $1,700
    Old World Auctions (June 17): Lot 20. Keulen's Spectacular Chart of the World Featuring California as an Island (1728) Est. $12,000 - $15,000
    Old World Auctions (June 17): Lot 42. Schedel's Ancient World Map with Fantastic Humanoid Creatures (1493) Est. $14,000 - $17,000
    Old World Auctions (June 17): Lot 591. Matching Set of 3 Stunning Globe Gores of Eastern Asia from Coronelli's 3.5 Foot Globe (1688) Est. $5,500 - $7,000
    Old World Auctions (June 17): Lot 9. Speed's Popular World Map with Allegorical Representations of the Elements (1651) Est. $14,000 - $17,000
    Old World Auctions (June 17): Lot 168. First Separate Map of Kansas & Nebraska Territories (1854) Est. $5,500 - $7,000
    Old World Auctions (June 17): Lot 43. Only Macrobius Map with Britain Attached to Europe (1515) Est. $800 - $950
    Old World Auctions (June 17): Lot 250. Rare Map of Boston and One of the Earliest Maps of the Revolutionary War (1775) Est. $2,000 - $2,300
    Old World Auctions (June 17): Lot 79. Schenk's Uncommon Map Featuring Two Figurative Title Cartouches (1696) Est. $1,200 - $1,500
    Old World Auctions (June 17): Lot 681. Hand-Colored Image of the Annunciation to the Shepherds (1502) Est. $800 - $950
  • Sotheby's Book Week
    2 June - 9 July
    Sotheby’s, June 25: Smith, Adam. The Wealth of Nations, on its 250th anniversary. $180,000 to $250,000.
    Sotheby’s, June 17: Fontana, Lucio. Concetto Spaziale. 1967. Leporello en papier doré. Bel exemplaire signé. €4,000 to $€,000.
    Sotheby’s, June 25: Fitzgerald, F. Scott. "So we beat on, boats against the current, borne back ceaselessly into the past”. $150,000 to $200,000.
    Sotheby’s, June 25: Washington, George (as First President). Washington decries “an ostentatious imitation, or mimickry of Royalty” in his Presidency. $250,000 to $500,000.
    Sotheby’s, June 17: Lope de Vega. Rare manuscrit autographe signé de la préface dédicatoire de "El Cardenal de Belen" (le cardinal de Bethléem), pièce composée en 1610. €40,000 to €60,000.

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