Dannemora Gets Lucky
A mobster's not-so-hard time at Clinton Correctional
by Michael Berdan
Which of Time Magazine’s 100 “Most Important People of the [20th] Century” had the closest ties to the Adirondacks? Theodore Roosevelt, who technically became president while vacationing here in 1901, would certainly be a good guess. But Roosevelt only popped in for a few weeks every now and then. Same goes for Albert Einstein. So if affinity is defined by longevity, the award goes to Charles “Lucky” Luciano, who spent—or more accurately “served”—six years at Clinton Prison, in Dannemora, just inside the Blue Line, and another four at the Great Meadow facility, just outside it.
Unlike TR, Lucky Luciano was already president of his own not-so-little political organization when he arrived at Dannemora on July 2, 1936, shackled to several other new inmates. Moreover, even in his “retirement,” Luciano continued to run his New York City criminal empire, approving new business deals, resolving “family” disputes and authorizing the occasional contract—the kind only one party signs.
Born in 1897 in Sicily but raised on the tough streets of Manhattan’s Lower East Side, Luciano (real name Salvatore Lucania) was straight out of central casting: a tightly built thug with wavy black hair, a pockmarked complexion, and a raspy voice that betrayed his impoverished immigrant origins and a wont of settling disputes nonverbally. Endowed with both vice and vision, Luciano was credited by crime writer Edna Buchanan with having “reinvented the Mafia” by “replacing traditional Sicilian strong-arm methods with a corporate structure, a board of directors, and systematic infiltration of legitimate enterprise.” The FBI itself cited Luciano’s ascendancy as “the watershed event in the history of organized crime,” according to Buchanan.
Already a rising star in the mob’s pre-Prohibition extortion empire, Luciano soared to prominence in bootlegging, eventually becoming Joe Masseria’s second-in-command. When the internecine Castellammarese War of late-1920s and early-1930s New York threatened to ruin it for everybody, Luciano did what many thought had to be done: he eliminated both the principals and established a single ruling body made up of putative equals, but with Luciano the acknowledged though uncrowned capo di tutti capi. Known simply as “the Boss,” Luciano, whose income was estimated at a half million dollars in the middle of the Great Depression, began living even larger: fancy suits, long nights on the town and a suite at the Waldorf Towers.
The repeal of Prohibition in 1933 led to Lucky’s demise. The extensive workforce required to smuggle and distribute booze (much of which came through the Adirondacks from Canada) needed a new, equally labor-intensive line of employment. Reluctantly, Luciano agreed to get into prostitution.
But prostitution, with its inherently unreliable customer and supplier bases, increased Luciano’s exposure, much to the delight of politically ambitious new special prosecutor Thomas E. Dewey. A 41-brothel raid on February 1, 1936, resulted in a 62-count indictment against the man Dewey called “Public Enemy Number One in New York.”
After a sensational and lurid three-week trial, Luciano and eight of his lieutenants were convicted on all counts and sentenced by Judge Philip J. McCook. As the boss, Luciano drew the longest sentence—not just of the eight, but of all time in the state of New York for compulsory prostitution: 30 to 50 years. He wouldn’t be even eligible for parole until 1956.
Going to Dannemora would not, however, be Lucky’s first trip to the North Country. In the early 1920s he had been hired by “the Big Bankroll,” Arnold Rothstein, to help run games of chance at the Brook, Rothstein’s upscale casino near Saratoga Springs, which catered to the well-heeled horsey set. Later, Rothstein staked Luciano and his buddy Meyer Lansky their own downmarket place, the Chicago Club, near the Saratoga railroad station. Ever since, Luciano had been an enthusiastic summertime visitor.
This summer would be different. “When they told me I was goin’ to Dannemora, I wasn’t sure I’d be able to take it,” he recalled in The Last Testament of Lucky Luciano, the memoir he dictated to screenwriter Martin Gosch in the early 1960s with the stipulation that it wouldn’t be published until 10 years after his death.
Known unaffectionately as “Siberia”—for its remoteness and bitter cold winters—Clinton Prison (now “Correctional Facility”) was, and is, a foreboding compound on a windswept rise overlooking the Saranac River Valley. Firmly believing that he would win his appeal, inmate #24806 resolved that he would be a model—albeit privileged—prisoner, a resolution no doubt appreciated by Warden William Snyder who assigned Lucky a cell in “the Flats,” the first-floor gallery in West Hall, that came equipped with an electric stove, curtains and a pet canary.
Lucky was less pleased with his assignment to work in the prison laundry. Neither the heat nor the physical labor suited him, and he didn’t cotton to being “some kind of washerwoman.” A couple hundred dollars—Lucky never wanted for cash—got him transferred to the prison library, where he was able to indulge a newfound interest in books about American history, geography and his native Sicily. He also worked diligently on his penmanship.
Lucky’s status and munificence cushioned him from most of the physical hardships of prison life. But confinement took a mental toll. He suffered from nightmares, and “whenever somebody from my family come up . . . I couldn’t talk to nobody for a week. I’d see my brother walk out and then I’d go back to my cell and hit my head against the wall. One time it started to bleed and they hadda sew it up.” While medics had him under the knife, they also sewed up his trademark droopy right eyelid, the result of a vicious beating by Masseria’s goons in October 1929. (Luciano had earned his nickname by living to tell about what was supposed to have been a one-way ride.)
In March 1937 Luciano was transferred to C Block, “one of the best and cleanest blocks,” according to James D. Horan, a fellow inmate who recalled his hard time with Luciano in his 1959 autobiography The Mob’s Man. Horan gladly accepted the daily job of cleaning Lucky’s cell and pressing his clothes (silk shirts and creased slacks), for which he was paid handsomely in cigarettes, candy and salami.
Luciano’s culinary needs were taken care of by “Little Davie” Betillo, his former first lieutenant, who had received 24 to 40 years for a supporting role in Luciano’s prostitution empire. In a corner of the prison kitchen that had been made available to him in exchange for some payola, Betillo prepared Luciano’s meals before serving them to him in the privacy of his cell, where the gangster would listen to comedy shows on the radio. (Lucky’s favorite was Abbott and Costello.)
This homey little arrangement came to an end when Luciano said something that infuriated his hot-tempered chef. Little Davie bit his lip and bided his time. Eventually he caught the boss alone and began beating him with a baseball bat. Another con heard the commotion and came to Luciano’s rescue, an act which apparently earned him an early release from Dannemora. After that incident Luciano never went anywhere on the grounds without a full complement of bodyguards.
Like most inmates, Luciano was greatly concerned with the progress of his appeal, whose first incarnation, procedural error, had been summarily shot down. Luciano’s lawyer, Moses Polakoff, brought in an even-more resourceful attorney, George Wolf, to assist in formulation of round two: an attempt to prove that the testimony of the main prosecution witnesses—three prostitutes—had been fabricated, coerced and rehearsed by Dewey himself. It would cost Luciano $90,000, but Wolf eventually found the women in Paris, where Dewey had sent them on an all-expenses-paid, extended vacation. Wolf got them to sign affidavits to the effect that Dewey had indeed given them the choice of either taking the stand against Luciano or going on trial themselves.
Meanwhile Luciano was making the best of his situation. On a hill overlooking a recreation area called “the Courts,” he drank coffee, played rummy and held court of his own with the prison’s extensive Italian population. They beseeched him for favors. Luciano pledged to do what he could, especially for the ones whose sentences were just about up and whom he thought could be useful to “the outfit.”
More important, Luciano continued to monitor business down in New York. Under the pretense of discussing his appeal, Polakoff routinely arrived at Dannemora accompanied by Luciano’s cronies. During visits the lawyer would discreetly withdraw so they could get down to business.
Around Easter 1937 Joe Adonis, Luciano’s liaison with the Unione Siciliano, arrived to clue the boss in on Meyer Lansky’s latest venture—a deal with Cuban dictator Fulgencio Batista for the gambling concession at Havana’s ritzy Hotel Nacional. Lansky was summoned and appeared within a week, convincing Luciano he knew what he was doing.
Later that year the topic was Dewey’s new target, racketeer Louis “Lepke” Buchalter. Luciano decreed that Buchalter should be taken into mafia protective custody. Two years later an FBI agent would pay Luciano a visit over still at-large Lepke. Luciano agreed to disclose his whereabouts (an apartment in Brooklyn), but only if J. Edgar Hoover would commute his own sentence. The agent refused. Not long after, Luciano, whose freedom was increasingly dependent on gubernatorial parole, tricked Buchalter into surrendering so that Dewey, an as-yet unannounced candidate, would owe him a favor. Buchalter would die in the electric chair in 1944.
In late 1940 Frank Costello arrived to break the news that “Kid Twist” Reles, Lepke’s former enforcer, was singing his heart out at the Brooklyn district attorney’s office in exchange for immunity in a mob hit. Luciano gave the matter some thought and decided to have Reles thrown out the window of his sixth-floor hotel room by the Brooklyn detectives assigned to protect him. The collective peace of mind cost “the outfit” $50,000 in payoffs.
But not all of Luciano’s conferences were business: “When I was at Dannemora, the fellas who come to see me told me about a skinny kid from around Hoboken with a terrific voice [who was] 100-percent Italian.” That kid was Francis Albert Sinatra, and Lucky okayed an investment of some $50,000 to “put Frank across with the public,” i.e., “for publicity, clothes, different kinds of special music things” to supplement the $150 a week he was getting from Tommy Dorsey. Sinatra would later show his appreciation by singing at Lucky’s mobster conclave in Havana on Christmas Eve 1946.
The mobster was generous inside the walls too. Between 1939 and 1941 inmates constructed St. Dismas, an ornate house of worship also known as the Church of the Good Thief. Luciano donated the Appalachian red oak that prisoners used to build pews.
In 1941 Warden Snyder was replaced by Dr. Walter Martin, who believed that his most famous inmate had been given too harsh a sentence, so he granted him more in-house privileges. But Lucky’s big break would come near the end of the year—on December 7—though at first even the calculating con couldn’t see the connection.
The link became clear seven weeks later when the Normandie, a French liner being converted into a troop ship, caught fire and capsized at a Manhattan dock. Though the fire appeared to be the result of worker carelessness, a suspicion of sabotage by German or Italian agents persisted. A Navy intelligence assessment of the mob-controlled docks identified Luciano as the only person who could guarantee the cooperation of New York’s predominantly Italian longshoremen.
Luciano agreed to give his word, but only if the Navy got him out of “this dump.” And so, on May 12, 1942, Lucky—along with eight others for the sake of obfuscation—was transferred to Great Meadow Prison, in Comstock. Though Comstock was also maximum-security, hard time there was softer, especially for the top-secret linchpin of “Operation Underworld,” who would continue to be of material assistance (though mainly to himself) during the war. In addition to an office, Luciano was allowed to have personal possessions in his cell and catered food. His real treats, however, were escorted outings to Albany and at least one night in a roadhouse, where he was granted a couple of hours alone with his longtime mistress, Gay Orlova.
By the time the war was over, Lucky was convinced that his parole was in the bag, especially since Dewey, who had been elected governor in 1942, wouldn’t want any witness-suborning charges leveled against him during a presidential run. But there was something else in that bag that Luciano hadn’t anticipated: mandatory deportation to Italy. It was an offer that even the boss couldn’t refuse. Luciano was released from Great Meadow on February 2, 1946, and taken directly to Ellis Island. There, in sight of the city whose criminal empire he once ruled, he spent his last week in America waiting for deportation paperwork. After a sumptuous party aboard the Laura Keene, Luciano set sail for Italy, where he would die of a heart attack 16 years later, at age 65.
Despite having gained his freedom 10 years before he was eligible for parole, leaving was painful. “I began to get this real sour feeling in my stomach, and when the pilot horn started to blow, the sound of it seemed to fill the inside of my belly,” the mobster recalled. “The only other time in my whole life that I had this kind of experience was when the gates closed behind me up at Dannemora.”