Nearly a century before hip-hop moguls flashed “bust-down” Rolexes, there was a different kind of titan setting the trend for audacious wristwear, and his name, Al Capone. The notorious Chicago gangster, a man synonymous with flamboyant style, wasn’t content with a “plain” Patek Philippe. His desire for ultimate bling led to a custom platinum pocket watch, encrusted with 90 diamonds spelling out his “AC” monogram, which is now slated to be a highlight of Sotheby’s upcoming Important Watches auction in New York.
This is a tangible piece of criminal lore. Capone, the “original Scarface” who defined the archetypal gangster image, reportedly took his Patek Philippe to a local Chicago jeweller with a very specific vision. The result? A solid platinum case, replacing the original and a daring customisation on the caseback. While today aftermarket diamonds are often looked down upon, on Capone’s watch, they tell a story of unparalleled audacity. As Geoff Hess, Sotheby’s global head of watches, notes, a custom gem-set case of this calibre “would definitely not have been standard, to say the least. He was a cutting-edge criminal!” and evidently, a cutting-edge watch enthusiast.

Image Credit: National Jeweler
The watch’s journey to the auction block is almost as captivating as its origins. This isn’t its first rodeo. In 2021, Capone’s direct descendants, inheriting the watch from his son Sonny, consigned it to Sacramento-based Witherells. Part of a wider estate sale dubbed “A Century of Notoriety” – which included Capone’s favourite Colt. 45 pistol and a diamond tie bar – the pocket watch vastly exceeded its pre-auction estimate of $25,000 to $50,000, ultimately fetching a remarkable $229,900. Experts even hailed that auction as “one of the most important celebrity auctions in history,” garnering over $3 million in total.
Now, Sotheby’s has stepped in, giving the iconic timepiece a fresh pre-sale estimate of $80,000 to $160,000. While its faded dial and missing minute hand might deter a purist seeking a pristine horological grail, its provenance and the sheer historical weight it carries make it an irresistible piece of memorabilia for collectors.
Alphonse Gabriel Capone’s life, from his humble beginnings in New York and his time with the ruthless Five Points street gang to his reign over “The Outfit” in Chicago, is the stuff of legend. Though ultimately brought down by tax evasion rather than rival gangs, his influence on American pop culture, inspiring countless films and novels, remains immense.

Image Credit: GQ
The upcoming Sotheby’s auction presents a unique opportunity to own a piece of this enduring legacy. While the Capone watch may not out-earn other rare Patek Philippe minute repeaters or the only-known example of a double-signed pink gold second series reference 2499 also on offer, for the right collector, Al Capone’s diamond-encrusted pocket watch will undoubtedly be the star of the show – a shining testament to the original gangster’s enduring style and notorious reputation. And with the US market currently enjoying a unique advantage for non-tariffed watches, the timing for American collectors couldn’t be better to acquire a piece of this extraordinary history.