This Thing of His: Kerouac and the Gambinos

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New York City is a crazy place. An asphalt jungle where artists and criminals inconspicuously overlap without looking in the mirror. But just how in the hell did an original manuscript—written by the king of the Beats, wind up in the home of one the Five Families’ capo di tutti i capi.

It was hand-typed by the delicate poet himself. A man who fluttered across America’s various landscapes like some Buddha Sage of edible language. Just filed there. Amongst the trash. It was even signed in green fountain pen chicken scratch by Kerouac himself.

Well…no one seems to have even the faintest of an idea.

The unpublished but “very significant” story was recently discovered among the possessions of an estate sale. Matter of fact it was nearly thrown out but saved. The sale in question was that of former Gambino crime family boss, Paul Castellano.

Ran the show for a pretty long time. Born in Brooklyn. Stayed in Staten Island. Murdered in Manhattan.

The beneficiaries of Castellano’s estate decided to auction off the gaudy Staten Island 18-bedroom mansion last year, which Big Paul personally commissioned in 1976. The idea was that it should resemble the White House. It took four years to complete and remains among the most opulent spectacles on Shaolin.

However, it was what lay inside the abode that others would find of great value. A so-called “lost chapter of the On the Road saga.”

The two-page manuscript was titled The Holy, Beat, and Crazy Next Thing.

The newly-found text was dated 15 April 1957, just five months before his magnum opus was published.

The newly-found text reads similar to the introduction of the book, but punchier and more reminiscent of Thompson’s Fear and Loathing intro.

“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.”

All these years later and his prose still reads energetic as ever.

The manuscript was discovered by Jerry Braunfield of Your Own Museum, a New York-based company that specializes in rare collectible artifacts.

He acquired it at the estate sale in November 2024. It remains unknown how or when it got into the hands of the Gambino leader but one theory suggests that it could have originally been given to one of Kerouac’s compatriots, perhaps in San Francisco.

“As was his known practice during this fertile time, he would often produce unique, typewritten pamphlets and chapbooks—sometimes referred to as ‘brochures’ by his circle—for friends, lovers, and patrons,” reads Your Own Museum’s description of the keepsake, which has since sold for $8,500.

“These were not commercial publications but rather personal literary artifacts, gifts from the artist himself, typed by his own hand on his signature long-sheet roll paper and often bound simply.”

It was never published and there has been no public record of it found anywhere.

This prompted a third-party investigation into its legitimacy, complete with lab tests and signature experts. All of which corroborated its authenticity. Another stunning aspect of the discovery was how meticulously preserved it was nearly seven decades on.

It offers an intimate peak through a special window in time. A crystallized stream of Kerouac on the precipice of altering American culture.

But why was it languishing away among the private files of Paul Castellano? Did the crime kingpin, who is believed to have ordered somewhere in the neighbourhood of 200 hits during his reign, have a soft spot for Beat poetry?

We’ll likely never know as “The Beak” was gunned down by the infamous John Gotti and his crew outside Sparks Steak House on a particularly brisk December evening in 1985. The blood drenched cement meant a changing of the guards for La Cosa Nostra. With Castellano gone, so likely too went the answer to our little mystery.

I remain baffled as to how their paths could have crossed. No close friend of Kerouac’s would have pawned off something so sentimental, even in tribulation.

But had they, it still doesn’t explain Castellano’s discreet possession.

Or is it something as simple as Kerouac and Castellano being a booth over from one another at some all night diner in Greenwich Village. One hopped up on bennies and the other ordering some with a side of cantaloupe. Perhaps a conversation kindled over sports or politics or weather. Maybe the odd couple bonded momentarily, who knows?

There is some irony in this revelation here but I just can’t quite put my finger on it.

Perhaps it’s that the work of a writer who notoriously lived life on the road–a poor vagabond–weary of any form of stability, would be uncovered in the 33,000 square foot palace of an ostentatious brute. Castellano barely ever left his house, let alone the neighbourhood. He notoriously self-isolated, unable to trust a soul.

He famously once said: “The law is-how should I put it? A convenience. Or a convenience for some people, and an inconvenience for other people. Like, take the law that says you can’t go into someone else’s house–I have a house, so, hey, I like that law. The guy without a house-what’s he think of it? Stay out in the rain, schnook. That’s what the law means to him.”

The law may have cut through Kerouac like a mean mountain wind down Larimer Street but he trusted the universe.

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