Diamond is forever…

    He was gunned down 70 years ago in an Albany rooming house, but Legs Diamond left behind a glamorous persona that has been harder to kill.

    Note: The following article by A Small American City Host Duncan Crary first appeared in the September 2002 issue of Hudson Valley Magazine. It has been revised and edited, but all references to dates are relative to 2002.

    THEY DUBBED HIM “LEGS” and the “Clay Pigeon.” They branded him a bootlegger, womanizer, gangster, and thug. He used the alias John Nolan.

    “Nobody who knows him calls him anything but Jack,” wrote Pulitzer Prize-winning author William Kennedy in his 1975 novel, Legs.

    Call him what you will. In his day Jack “Legs” Diamond was the most visible and glamorous gangster of them all, with a fashionable hat tipped rakishly askew and a swell wardrobe to match. On one arm was his faithful wife, Alice; on the other: the sassy redheaded actress-turned-gangster’s-girl Marion “Kiki Roberts” Strasmick.

    Legs had it all. Until it all came crashing down one night in an Albany rooming house, on December 18, 1931. But that hasn’t stopped the underworld’s glitziest villain from resurfacing in movies, novels, and even a Broadway musical. Just this year, he returned from his unconsecrated grave in Queens to make a cameo in Roscoe, the latest installment of Kennedy’s growing “Albany Cycle” novels.

    “The bullet hasn’t been made that can kill me.”
    — Ray Danton as Legs in The Rise and Fall of Legs Diamond

    Even after all these years, whether in fact or fiction, you don’t have look hard in Albany to find a story with Legs.

    On Jefferson Street, a few blocks from where Diamond finally cashed it in, the Palais Royal bar seems to have hardly aged since that night 70 years ago. Though the watering hole has moved up the street since the Prohibition, owner Rocky Nigro, 91, still keeps the spirits of the time alive. With a little coaxing, the seasoned bartender starts to talk about his early days in the city. His father, Leonardo, ran speakeasies all over town during Prohibition, and one of Nigro’s fondest memories was the time the dapper Diamond popped in for a drink.

    “Legs gave me a 15-cent tip for shining his shoes. That was a lot of money for a 16-year-old kid,” he says.

    But while there may be a lot of stories kicking around town about the man, it’s lesser known how he ended up kicking around here.

    JOHN DIAMOND WAS BORN IN PHILADELPHIA to poor Irish immigrant parents in 1897. The family relocated to Brooklyn in 1913.

    At the time, Irish-Americans were just starting to break free from their clapboard ghettos through honest work and assimilation. But Jack and his younger brother Eddie opted for a life of crime and violence instead.

    Diamond’s ambition quickly brought him into the service of Arnold “The Brain” Rothstein. Known as “King of The Roaring Twenties,” Rothstein is said to have masterminded the 1919 World Series fix among other notorious 20th-century scandals. (He supposedly inspired the character Meyer Wolfsheim in The Great Gatsby and Nathan Detroit in Guys and Dolls.) Rothstein hired Diamond to strong-arm strikers in a labor dispute. Soon after, he made Diamond his personal bodyguard and hitman.

    “AR” relied heavily on Diamond’s protection during his reign as kingpin. But in 1928 he was gunned down and went to his grave refusing to name the killer. Gary Levine’s biography, Anatomy of a Gangster: Jack “Legs” Diamond, proposes that Rothstein’s own bodyguard pulled the trigger. If so, Diamond had good reason. A year earlier, Legs had been the victim of a double cross: Rothstein had set him up on drug charges to avoid arrest himself.

    Rothstein’s murder, just one of many that Diamond committed or authorized, set off a chain reaction the country is still recovering from. Almost overnight, inner- city punks and hoods became the richest and most powerful men in the nation by, in gangster Dutch Schultz’s words, “giving Americans what they wanted.”

    During Prohibition, what they wanted was liquor. By 1930, the illicit whiskey and beer trade in New York was big business, and competition had grown fierce. Not satisfied with only a piece of the pie, Diamond was determined to rub out all of his rivals in one fell swoop. His plot was foiled when city police confiscated his cache of arms and ammunition — pistols, machine guns, tear gas bombs, even hand grenades. It was the largest stash of weaponry ever seized by NYC cops — enough firepower to make the St. Valentine’s Day Massacre look like a cap-gun fight.

    Defenseless in the “Big City,” Diamond retreated upriver to Greene County to strengthen his hold on liquor smuggling in the rest of the state.

    “Legs gave me a 15-cent tip for shining his shoes. That was a lot of money for a 16-year-old kid”
    — Rocky Nigro

    THE CATSKILLS WERE RIPE for Diamond’s illicit activities, and soon his goons were terrorizing the mountains. In his spare time, Legs liked to strut his stuff on the dance floor of the Catskill Mountain House, showing off the fancy footwork that some say earned him his moniker.

    There were enough classy resorts in the Catskills to keep Diamond entertained but the allure of the Rain-Bo Room in Albany’s ritzy Kenmore Hotel often enticed the gangster and his showgirl away from his mountain hideout.

    During the ‘20s and ‘30s, the Kenmore was the place to be. Big acts like Duke Ellington traveled to Albany to broadcast nationwide over the Rain-Bo Room’s WGY radio hook-up. During the last years of his life, Diamond had his own corner spot in the bar. (Today, instead of serving bootleg whiskey and gin at its North Pearl Street address, the Kenmore serves as office and retail space.)

    Diamond made his final appearance at the Kenmore on the last night of his life. During the previous spring, he had simply gone too far in the Catskills. Wanting in on the local applejack trade, he had assaulted bootlegger James Duncan and kidnapped and tortured Grover Parks, who had refused to reveal to him the whereabouts of his still.

    Diamond made his final appearance at the Kenmore
    on the last night of his life.

    GOVERNOR FRANKLIN D. ROOSEVELT PUT HIS FOOT DOWN. The State of New York had tolerated a multitude of illicit activities resulting from Prohibition, but kidnapping and torture crossed the line. So FDR’s men stormed Diamond’s Acra compound to round up the gang and press charges.

    Diamond’s ingenious lawyer, Daniel Prior of Albany, had the trial moved to Troy, where he retained local attorney Abbott Jones as co-counsel. The Collar City has not forgotten the infamous case. Today, Abbott Jones’ grandson, E. Stewart Jones Jr., heads the esteemed family practice that continues in Troy. A photo of the Diamond trial in progress decorates the first floor of Jones’ Second Street firm.

    “Abbott Jones was regarded as a top cross-examiner of his time. He was the most prominent lawyer in Rensselaer County, and he greatly improved Diamond’s image in the trial because he lent credibility as a former judge and DA,” says Jones of his grandfather.

    Jones adds that there was no chance of convicting Diamond in Rensselaer County, where he was seen as a Robin Hood-type folk hero. “On his way to the trial, Diamond was passing out $20 bills to the people on the street.” He was acquitted on December 17, 1931.

    While the trial brought Abbott Jones fame and notoriety, that’s all he got. “Legs owed my grandfather $15,000,” explains Jones. “He had the cash on him the day of the trial, but he made plans to pay my grandfather later. Legs was murdered that night in Albany, but when the police found the body there was no money on it. So Abbott Jones never got paid. “That’s why in this profession you ask for the money up front,” Jones said.

    “That’s why in this profession you ask for the money up front”
    — Abbott Jones as quoted by E. Stewart Jones, Jr.

    THE OFFICIAL RECORD of what led up to Diamond’s murder remains murky. Following his victory in Troy, Diamond crossed over the Hudson to celebrate in Albany with Alice and Kiki. Afterwards, he put up his two women in their apartments while he retired to less luxurious digs on Dove Street. Sometime during the night, after stumbling upstairs to his bed, he was killed by three bullets to the head.

    To this day, the identity of the murderer (or murderers) remains a mystery. At the time, some suspected Dutch Schultz. Others pointed the finger at Alice Diamond, forever jealous of her husband’s extramarital relationship. William Kennedy poses another theory in his 1983 non-fiction collection 0 Albany!: Dan O’Connell, boss of Albany’s infamous political machine, ran the beer trade in the city during Prohibition, and he wasn’t about to let Legs muscle in on the business. Though short on cash, Diamond was reported to have quite a bit of booze stashed in the area. The idea of running hooch in Albany appealed to him, and the machine was well aware of his intentions.

    In 1974, Kennedy broached the topic with O’Connell. “Prior brought him around here — but he brought him around once too often. Fitzpatrick finished Legs,” Kennedy quotes O’Connell in the book.

    William J. Fitzpatrick was an Albany cop who worked for O’Connell. While no one knows for sure if Fitzpatrick actually pulled the trigger that night, Kennedy settles all doubts in his fictionalized account of the event in Roscoe. Fitzpatrick and fellow cop Jack McElveney appear as characters “O.B.” and “Mac,” who murder Legs for O’Connell’s persona, Patsy McCall.

    The headline-making slaying of Jack Diamond was a mystery, Kennedy explained to a crowd at Schenectady’s Union College, assembled last spring for a reading from Roscoe. “I presume to solve it”

    Diamond himself makes a few brief appearances in the novel, and Kennedy says that’s not the last we’ll see of him. While writing the screenplay for Francis Ford Coppola’s The Cotton Club — in which Legs’ nemesis, Dutch Shultz, plays a major role — Kennedy and the director entertained the possibility of filming a cinematic version of Legs. The movie was never shot, but Kennedy did acquire the notorious Dove Street boarding house in anticipation of filming. He uses it today as his writing studio.

    “There are no bullet holes in the wall; they’ve been taken out” — William Kennedy

    “There are no bullet holes in the wall; they’ve been taken out,” Kennedy told the disappointed Union crowd. Then he made it up to the audience by informing them that Ed Burns, director of The Brothers McMullen, now has the option of co-writing, directing, and starring in Legs.

    In an earlier film, The Rise and Fall of Legs Diamond, actor Ray Danton, playing the gangster, exclaims, “The bullet hasn’t been made that can kill me.”

    That bullet was made, but it couldn’t keep him down for long.

    Duncan Crary is a writer/podcaster based in Troy, N.Y. His great-grandfather, John Crary, covered the Diamond gang Catskills roundup for the New York Sun. Before moving to Troy, Duncan lived on Iriving Street in Albany, a few doors down from where his great-grandfather lived during the 1930s. Family legend has it that John Crary was the first reporter on the scene of the Dove Street Diamond murder, which was just three blocks away from his home. He was said to have been tipped off about the hit before it went down.

    [Update: Palais Royale proprietor Rocky Nigro died in December, 2004 at age 94. A Hollywood film based on Kennedy’s novel Legs has yet to be made.]


    • Legs Diamond mugshot. Photo by New York City Police Department
    • Duncan Crary, Rocky Nigro & unidentified woman at The Palais Royale, Albany, NY. Photo by Cal Crary
    • Postcard: The new Kenmore Hotel, Albany NY
    • Legs Diamond Trial, Troy NY 1931. Photo courtesy of E.Stewart Jones Law Firm
    • William Kennedy with his wife Dana and granddaughters in front of their Dove Street row house where Legs Diamond was murdered. Photo by Brendan Kennedy.
    • New York Sun articles about Legs Diamond by John Crary. Photo by Duncan Crary.


    William Kennedy's Prohibition Story - Still

    [From left to right: Matt Ryan, Chris Ryan, and Duncan Crary (as bartender) at Ryan’s Wake Public House, Troy, NY. Actors playing Legs Diamond and henchman in background. Photo Courtesy of WMHT.]

    In 2011, A Small American City Host Duncan Crary made a cameo appearance as a bartender in the public television documentary film, William Kennedy’s Prohibition Story.

    You can watch that scene here:

    Or you can watch the entire 30 minute film online here.

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