Two years ago, what might’ve otherwise been an unremarkable real estate transaction in Albany’s Center Square neighborhood tumbled into the New York Times’s estimable spotlight. That’s because the unassuming 19th century brownstone at issue was no ordinary home; rather — and far more notoriously — it was the final resting place of Prohibition Era Albany’s most notorious gangster.
That’s how 67 Dove Street inspired “Jack Diamond’s ProhibiGin” (pronounced “prohibition”), an 82-proof London dry gin that reinvigorates the flamboyant mythology of upstate New York’s erstwhile hometown bootlegger.
Where the Dead Come Alive
“You could call us Albanyphiles,” New Scotland Spirits owner Jim Muscato says of his fellow partners in their Albany County-based craft distilling outfit, “but that’s probably too generous. We’re just local history nerds.” He gestures to the faded framed newspaper clippings adorning the wall of his company’s tasting room. “Can you tell?”
Jesse on the steps of 67 Dove Street in Albany
For an enterprise that famously stakes its brand identity in regional imagery, lore, and symbolism, the Tasting Room at the corner of State and Lark Streets stands out as a notable showcase. Aesthetically recalling century-old speakeasies empaneled with tin ceiling tiles and leather button-tufted sofas, its décor is punctuated by antique clocks, telephones, radios, and a ninety-year-old oak-and-mahogany bar to which Albanites once bellied up back when it lived a block away inside the old Larkin Restaurant.
Yet the Tasting Room’s most engrossing design flourishes are the literary portraits of Albany’s 20th century apex personalities — figures like Dan O’Connell and Erastus Corning 2nd — who intractably ruled New York’s capital city for more than 50 years at the intersection of politics and profit, power and patronage. The newest addition to this storied lineup is a hundred-year-old black-and-white mugshot depicting what was then one of the planet’s most recognizable faces: Jack “Legs” Diamond.
“Our [brand] labels exude a reverential sense of place,” says owner Jon Berquist. He’s been friends with New Scotland Spirits founder Jesse Sommer since nursery school; the company derives its name from their shared hometown (New Scotland). “But really it’s the people who give a place any meaningful significance, and few things symbolize ‘Albany’ quite like Legs.”
A Ghost of the Past Yields a Spirit in the Present
How Legs Diamond earned his moniker is a mystery; speculation most commonly credits his skill on the dance floor. The Philadelphia-born Irish-American gangster spent his formative years in New York City, was imprisoned at Leavenworth for desertion from the Army during World War I, and then cut his teeth in the criminal underworld as a hired gun for the Jewish mob. But it was America’s disastrous enactment of the Constitution’s Eighteenth Amendment that turbocharged Legs Diamond’s racketeering, ultimately catapulting him to superstardom, infamy, and eventually…an early grave.
Legs had been illegally selling alcohol at a speakeasy in Manhattan when gangland turf wars forced him from New York City to Kingston. There, his elaborate manufacturing operation — at which point he pumped beer via rubber tube through the city’s sewer system from an illicit brewery to a nondescript warehouse for bottling — was eventually shut down by the Feds in what became known as “the million dollar raid.”
So Legs again moved north, this time to Albany’s neighboring Greene County, wherein he discovered that robbing his bootlegging rivals of their liquor was much less hassle than distilling his own. But this netted him scores of enemies, a dozen assassination attempts, and multiple arrests leading to prosecutions which somehow never resulted in conviction. The media spectacle surrounding each gunshot wound and every acquittal rendered him “the Hudson Valley’s biggest celebrity, a symbol of the little guy standing up to the heavy government hand of Prohibition.”
Indeed, Jack Diamond’s renown directly proceeded from tabloids eager to sell papers with colorful reports of his even more colorful antics. In one of the many instances where Legs was rushed to a hospital riddled with assassins’ bullets, the New York Times seemed almost delighted to quote the attending physician’s prognosis that “there was practically no chance of recovery” — because, by this point, Legs had already received the nickname “clay pigeon of the underworld”; his recovery from this latest attempt on his life only furthered his seeming invincibility. NYC Police Commissioner Edward Mulrooney had reportedly asked Legs how he’d managed to crawl his way to rescue with five wounds. The indestructible clay pigeon replied: “I took two good shots of whisky and was able to make it.”
But Legs was no match for Dan O’Connell, himself a bootlegging brewer who pulled-double duty as head of Albany County’s Democratic political machine and its adjacent criminal syndicate. Legs disregarded O’Connell’s direction to skip town and instead setup a network of speakeasies and brothels mere blocks from the current site of the New Scotland Spirits Tasting Room. After months of antagonizing rivals and law enforcement alike, consequence caught up with Legs following yet another acquittal (this time on kidnapping charges) in neighboring Troy.
No shooter was ever identified, but history affords little wonder as to who ordered the hit.
It’s the bloody circumstances of Jack Diamond’s last moments on earth that are now memorialized on a New Scotland Spirits bottle of London dry gin, the label reads:
Destiny found Jack “Legs” Diamond in a rented bed on Albany’s Dove Street, sleeping off a celebratory gin-soaked evening in the wake of yet another acquittal. He’d been shot eleven times in the past, but this time the .38 caliber pistol which thrice split the night in those wee hours of December 18, 1934, left nothing to chance….
“Gentleman Jack” was a fixture in the Prohibition Era Hudson Valley, bootlegging “bathtub gin” from the Helderberg Mountains to the speakeasies of New York City. Yet Legs himself was no distiller; he was a highway robber who hijacked booze from illicit stills for which the law was no recourse.
Rakish scofflaw, debonair scoundrel, underworld rockstar. WOMANIZER.
Media darling, populist hero, celebrity gangster. MURDERER.
This is how New York tabloids described the Eighteenth Amendment’s most notorious rebel. And while his assassins were never found, Albanites of a certain era have no need to speculate. For it was Dan O’Connell’s Albany, but it was Jack Diamond’s Prohibition.
A Modern Day Media Spectacle
The release of Jack Diamond’s ProhibiGin will be exactly one month overdue when it hits shelves on Monday, July 14th, 2025.
“June 14th was World Gin Day,” says company owner Rosamaria Luppino. “Our product launch was supposed to coincide with the global celebrations, but we couldn’t rescue Jesse from his neurotic paralysis. He demanded forty — literally forty — pointless [label] redesigns.”
Jesse, who conceived the gin’s label, disputes his partner’s critique. The task of bringing his artistic vision to life fell to company owner Brian McGregor (the graphic artist responsible for all of the company’s product labels), and Jesse “salutes Brian’s heroic patience” throughout a process he knows he “made a bit more cumbersome.” But he doesn’t apologize for any delays.
“This label had to be perfect — historically accurate, artistically dramatic, and sensitive to Jack Diamond’s legacy while also recognizing that the dude was a malignant sociopath.” Jesse dishes it right back to his partners. “You can’t rush perfection. I would’ve expected my colleagues to understand that, given that we distill whiskey.”
But his partners very plainly don’t understand that, as evidenced by the fact that several of them took to the company’s social media accounts to publicly shame Jesse for repeatedly postponing the gin’s release.
“Watching my son graduate high school might someday prove to be my proudest moment,” says Jim. “But, so far, nothing rivals the satisfaction I felt when a complete and total stranger approached us on Congress Street in Saratoga Springs and demanded that Jesse explain why he was taking so long to approve the gin label design. That was a magical demonstration of a community coming together.”
Jesse says he wishes Jack “Legs” Diamond were still around today. “First, I’d want him to see that he’s still getting attention in the media, even if it’s just on our Instagram account. And second, I’d want him to stuff Jim into a burlap sack and dump him in the Hudson River.”
