Auction Results

The Mafia boss and the Beat writer and the missing story 

By
15 October 2025 10:08
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Jack Kerouac's signature at the end of a manuscript of his unpublished story The Holy, Beat, and Crazy Next Thing, a "lost chapter" of On the Road, written in 1957
Image courtesy of Your Own Museum.

A previously unknown work by the most celebrated Beat Generation author, that was discovered in a mafia boss’s collection, has been sold by a New York collectibles dealer.  

The story is a 1957-written, two-page manuscript and is signed by Jack Kerouac in green fountain-pen ink. 

It was listed and then sold this month by Your Own Museum (YOM) with a published price of $8,500 (around £6,300), and an origin story tracing it back to the Gambinos, a New York mafia gang.

The text is entitled The Holy, Beat, and Crazy Next Thing. 

The previously unpublished short story tells a tale that Kerouac repeated in On The Road, his landmark Beat novel that was published just five months later.

It has been described as “very significant” by Kerouac specialist Dave Moore and sellers YOM say it looks like an attempt by Kerouac to develop the characters for his best-known work.

Kerouac looking uncharacteristically kempt in his naval reserve enlistment photo from 1943. He lived fast, and died, aged just 47, in 1969.

The document was previously owned by Paul Castellano, the head of the Gambino gang. He was murdered in 1985 on the orders of John Gotti, the “Dapper Don” who took over the clan not long after.

This document was found in a sale of Castellano’s papers and was probably acquired by him from a Beat poet in Kerouac’s circle. 

Jerry Braunfield of Your Own Museum, told the Guardian: “Preceding the sale of the property [Castellano’s Long Island mansion], the beneficiaries organised a private auction of Castellano’s collection. The amount of time Castellano owned this piece is unknown, however it has never been seen on public records.”

Kerouac is highly collectible. The scroll of paper on which he wrote On the Road, all 120-feet of it, realised $2.4 million in 2001. Signed first editions of On the Road can sell for thousands or tens of thousands of pounds depending on their condition.