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Sinatra's Havana Nights

Far from the maddening crowd of fans, Frank Sinatra found secret pleasures, and friendships with American mobsters, in pre-revolutionary Cuba
| By Bill "Guillermo" Iezzi | From Camilo Villegas, July/August 2006
Sinatra's Havana Nights

Who knows what the agile old man is thinking as he slips out of an air-conditioned, Korean-made Tico and looks up at the entrance to Hotel Nacional, the venerable Grand Dame of Havana? Frank Sinatra's baritone voice is still resonating over the car's radio: "…Like a soft evaaasive mist, you arrr, Bonitaaa, you fly away when love is newww…" Maybe 83-year-old Jorge Miguel Jorge Fernàndez's thoughts are with "La Voz," whom he knew personally at the hotel during more exciting times, back in the '40s and '50s when Havana's nightlife was the envy of the world. Sinatra's voice on the radio is richer, lower, more like a cello than than before when it was softer, higher, like a violin. But there is no mistake about whose voice it is.

As Jorge Jorge, as he is known, waits in the tropical night air for his American acquaintance to alight from the tiny Asian auto, a black Plymouth taxi from the '40s pulls up. The old Cuban looks at the antique and its occupants and cocks his head like an eagle. He does that when he listens or is in deep thought. And now, as he sees his reflection in the cab's window, he stands transfixed and perhaps transported to another time, when he'd stop in the same spot among La Voz and legends of the underworld such as Meyer Lansky and Charles "Lucky" Luciano.

Those were the days when Havana was the Paris of the Americas, a place where high rollers could mambo their way to six casinos, cabarets with exotic showgirls, a horse-racing track, jai alai games and brothels during a weekend trip from Miami. If Havana was Paris, the Nacional was the Eiffel Tower. If Sinatra was "The Voice" that made young women scream, the Nacional was the place where he whispered. Havana was his getaway, the Nacional his fortress. Or so he thought. He didn't count on the memory of Jorge Jorge or the watchful eyes of government agents from the United States.

Now inside the lobby, Jorge, galvanized by the electric atmosphere of the hotel's anniversary celebration, turns left and heads for the swimming pool bar faster then a waiter smelling a big tip. He poses for a shot under a 1959 photo of him and Fidel Castro and another in front of a mural in which Sinatra and Ava Gardner share the wall with Mickey Mantle, Rocky Marciano and other sports and entertainment figures of the time. He also holds up a photocopy of a Sinatra picture, declares that it was snapped in the Nacional's banquet room on December 24, 1946, and autographs it without being asked.

What else would you expect of a man who says: "I am the living history of the Hotel Nacional"? Indeed, Jorge's knowledge serves as a Hotel Register for the good times in Havana. He was there in 1946ó47 during the clandestine Havana Conference, in which Luciano and Lansky were joined by reputed mobsters from all over the United States gathered to pay tribute to Luciano, the Boss of Bosses, who'd been deported by the United States to his native Italy. The gang included the Who's Who of underbosses: Joe Adonis, Alberto Anastasia, Giuseppe Bonanno, Frank Costello, Vito Genovese, Giuseppe Magliocco, Willie Moretti, Augie Pisano, Joe Profacci, Santo Trafficante and others. They arrived at the hotel in fleets of taxis, with their bodyguards. And Jorge was there, taking care of La Voz, who brought his voice, and maybe more if a muckraking journalist can be believed.

Slim, fit and average in height, Jorge still has enough hair to comb along the sides of his head. He wears oversized eyeglasses whose lenses magnify his dark-brown eyeballs, making them look as though they're peering out of a fish bowl. A large proboscis gives his voice some timbre, especially when he talks animatedly about the old days. Indeed, it is the past and Jorge's link to it that has brought the mustachioed octogenarian and the grand septuagenarian edifice together on this humid December evening, the 73rd birthday of Her Majesty, seated like a queen on a cliff overlooking the Malecón, Havana's famed ocean boulevard, and the Atlantic Ocean that rolls all the way to Miami. Jorge is a special birthday guest of the striking stucco senora, which looks like a younger sister of the Breakers Hotel in Palm Beach.

Earlier, two doormen in white uniforms had politely ushered Jorge through the portico and into the stately building in which young Sinatra long ago had been elusive, like Bonita. Sinatra's habits and the hotel's operation had been quite familiar to Jorge, the only known living Cuban who was acquainted with the crooner and even lit his Montecristo cigars.

Jorge worked at the Nacional during the period when The Voice, and the hotel, held secrets. To hear him tell it, he made his way up from box boy (bellhop) to room-service waiter/interior decorator to casino manager. Jorge, a workers' representative, made the leap to management when Fidel's soldados were at Havana's doorstep on the eve of the January 1959 coup d'etat and the Lansky group needed someone it trusted to take over in a hurry. Jorge still wears a red-and-gold oval medal of a man on a horse. The small pin recognizes his service to the revolution in which Fidel overthrew President Fulgenico Batista, the casino business partner of Il Capo de Tutti Capi and Lansky. With Batista's blessing the Syndicate, or La Cosa Nostra as it was called then, had rented hotel and cabaret space to operate a half-dozen casinos throughout the Cuban capital during the 1940s and '50s.

Jorge reportedly enjoyed a good relationship with the mobsters, the rebels and La Voz in the fun-filled '40s, as well as the perilous '50s. He was sort of a double agent then, quietly raising money for the rebels, recruiting fighters and engaging in what he called "subversion," while being a fly on the walls of underworld guests. In the state-run newspaper Granma International, writer Joaquin Oramas describes Jorge as a "retired captain of intelligence." In the December 29, 2002, article, titled "New Year's Eve in the Parisian Casino" (the name was changed from Gran Casino Nacional in 1954ó55), Oramas says gangsters left the casino and $250,000 in a bank account in Jorge's name. They figured that the revolt would be over in a few months and then it would be business as usual. Forty-seven years later, the revolution is still revolting to the old mobsters, who say that more than $1 million was given to Fidel or his brother, Raul, to keep the casinos open.

Meanwhile, the money in the bank account vanished, according to Jorge. At a pork-and-rum restaurant in his General Suarez neighborhood, the twice-divorced grandfather waves documents dated September 29, 1961, showing a total of $169,799.22 under his name in the Banco Nacional de Cuba. He never saw a penny of it, he claims.

At the Nacional in the '40s, Jorge was an honest, efficient and creative worker. What endeared him to Lansky was news that Jorge had refused to accept money for designing the interior of the Plaza Hotel's casino. He declined the dinero, he told a Lansky lieutenant, because he already had a paid job at the Nacional, whose casino decor he'd originated. His reward was $100 dinner tips and room-service duty for Suite 212, rented permanently by Lansky, the Mob's gambling genius. Room 212 overlooks the Nacional's gardens, in which families of domesticated turkeys still peck along the grass and flamingos strut among groups of guests who rove like the birds and gabble in languages that only a polyglot can understand. Lansky's suite included the room in which La Voz stayed. Other rooms in the suite housed other famous figures of the times. Some of their black-and-white photographs hang on the walls of the pool bar. A head shot of Trafficante suspends above one of the King of Swoon, under which a caption reads: "Frank Sinatra, visitó el Hotel Nacional en las decadas 40 y 50." On another wall is a larger photo of Trafficante being led away by FBI agents.

Photos everywhere are reminders of the hotel's history, which coincides with that of the revolution. History also is the reason why the Sinatra photo that Jorge held and autographed was available only as a photocopy, made at the Hotel Capri, a block from the Nacional, six months earlier. "You can't sell history," said Jesus, head of the Capri's renovation project, when the American offered him $100 for the shiny black-and-white photograph. So he had an assistant make a photocopy for the foreigner, who returned before and after the birthday party to learn that the photo had disappeared. So much for not selling history. The photocopy shows a baby-faced, thin, young man with big ears in a light-colored suit and dark tie. His left hand is holding a pole supporting a microphone; he appears to be singing in front of a group of musicians. Underneath is the caption, "Frank Sinatra, cantante nortamericano que se dice: Que estuvo vinculado a la mafia [he was linked to the Mafia]."

Well acquainted with the history of the Mob's attempts to assassinate their legendary leader in the 1960s, older Cubans who speak about Sinatra always start by praising his musical talent and end with his being connected to the Mafia. Osdalgia, considered by some to be the Sinatra of Cuban song because of her elocution, passion and lyrical colorings, does so. Estela Rivas, director of historical records at the Nacional, does so. And Jorge, whom the historiador recommends to those seeking information about the hotel's past, does so, expansively.

"The Hotel Nacional was the only hotel in Cuba which could guarantee the secret of Frank Sinatra being here," Jorge says after the hotel's anniversary celebration, from his apartment near the Plaza de la Revolution. "It was a secret because he was working for the Mafia. Frank Sinatra didn't want anyone to know that he was here."

If the Swoon Master did work for the underworld at the Nacional, he did the same thing all performers had done for the identical crowd in New York, New Jersey, Chicago and Miami nightclubs: singing and shaking hands. The gangsters controlled the venues in which the entertainers worked. But skinny Frankie was special. He was what you might call a big earner for the Mob, and sometimes he sang for free. His generosity, one theory goes, was due to Frank Costello's successful intervention with Tommy Dorsey, who'd signed the youngster to a lifetime contract that left him splitting his income almost in half with the vindictive band leader who wouldn't release him from it.

Jorge says he'd heard Sinatra sing once or twice in the hotel's banquet room, now the Parisian Cabaret, during lunch breaks at the Mob conference that started on December 13, 1946. La Voz had been a special guest. The songs he sang were beyond the recollection of the old man, but he designated the nortamericano the best singer in the United States. Senor Sinatra could be "unkind" when he was drinking, Jorge recalls, but overall he liked the entertainer because he was amiable, sociable and kind. "We were almost friends," Jorge says.

Then he adds something that strongly suggests that time and ego can alter a man's memory. Jorge says he had no compunctions about having a weeklong affair with Gardner in the winter of 1951, when Sinatra, who'd introduced Jorge to his bride, was called to Las Vegas during their 15-day honeymoon. Neither Rivas nor an interpreter, Wilmer Morales, believed the tale, although the translator conceded that the affair could have lasted an afternoon.

"I had no guilt. I was sad because we had only a short time together," Jorge says. "She was like Miss Universe. She had a perfect body, face. She was a beautiful woman. I fell in love with her and I'm sure she liked me more than Frank Sinatra."

While there's little doubt about Sinatra's ties to well-known mobsters, the allegations that he worked for them aren't universally accepted or directly acknowledged. Interestingly, Tina Sinatra addressed the subject with terminology that is often echoed in circles of older New York Italian-American men, who may or may not have had ties to that era. In her book, My Father's Daughter: A Memoir, she says, "A favor was paid, and a favor was owed," referring to her father asking racketeer Sam Giancana to get out the vote for John F. Kennedy in West Virginia and Chicago during the 1960 presidential campaign.

While FBI files on Sinatra document some of the crooner's trips to Havana, it may not have covered them all. One old-timer recalls a 1950 trip to Cuba that isn't in the files. But any comments about what trips he did or didn't take inadvertently raise the issue of Sinatra's hidden life in Havana. The clandestine nature of the singer's Havana visits (Jorge says the first was between December 15 and 26, 1946) was maintained by his not signing the hotel's register, according to Jorge, who said he went directly to Lansky's suite. In addition, Sinatra sang only for the Mob, according to Jorge, who says he often saw him in Lansky's quarters.

However, the old man's claim that the organization's favorite songbird never flew from the hotel is refuted by Scripps-Howard newspaper chain columnist Robert C. Ruark and Cubans who saw him at the Tropicana with bailarinas. Ruark wrote that Sinatra was seen with Luciano at the racetrack, the Gran Casino Nacional and special parties. Sinatra later said he went to a sports event and visited nightclubs, trying to explain away his being in the vicinity of the mobsters.

Young Blue Eyes' silent agenda in Havana was to run with capos and showgirls far from the American press, which had turned against him in the mid-1940s. Some fans had flipped on him, too, at least partly because he was annoyingly temperamental, but also due to questions about his draft status and politics as well as his association with the underworld.

One thing is clear: Prohibition-era gangsters who later opened their clubs to Sinatra regarded him as their own bad boy. At 5 feet, 7 1/2 inches and 119 pounds, the puny physical stature of the 31-year-old singer in 1947 belied a muscular social conscience. He was the featherweight champion of the underdog and he condemned racial and religious intolerance at a time when stars didn't do that. He wrote pamphlets about tolerance, gave speeches on the subject and made a film short called The House I Live In, in which he taught a group of young boys a lesson in religious tolerance. Bad boy even slugged a few bigots and spoke about his liberal political views fearlessly in the face of commie chasers, prompting attacks by conservative columnists. So when someone filmed him disembarking from a Pan-American Airways Yankee Clipper with two wiseguys in Havana on February 11, 1947, and Federal Bureau of Narcotics agents spotted him in the midst of the ongoing criminal conference, they leaked the information to Ruark, who was on the island to interview author Ernest Hemingway. Thus began the public perception of Sinatra as a friend of underworld figures, if not one himself.

Ruark received the news about Sinatra after the singer left Havana for Mexico on February 14. The writer pieced the story together and excoriated the entertainer for associating with Luciano—the New York Boss of Bosses—and other Mob chieftains in Havana, where they'd been seen carousing. Demoralized by the news account and others that followed, Sinatra issued the first of two statements: "I was brought up to shake a man's [Luciano's] hand when I'm introduced to him without first investigating his past. Any report that I fraternized with goons or racketeers is a vicious lie," he said, according to author Arnold Shaw. (The singer's second statement would come in 1952.)

Lee Mortimer, entertainment editor of the New York Daily Mirror, trailed with a story in which he called Sinatra fans morons for their love affair with a Mob associate. The singer responded by punching the writer on April 8, 1947, in a Hollywood nightclub.

Mortimer had him arrested, and on May 13, 1947, went to the FBI with a photo of Sinatra and a mystery man (Joe or Rocco Fischetti) stepping from an airplane in Havana, and asked for help in identifying him, according to the bureau's records. The editor also requested information on the Hoboken singer's arrest record in Bergen County, New Jersey, on a 1938 sex charge (later dismissed), his association with New Jersey Mob boss Willie Moretti, and information in his Selective Service file. Director J. Edgar Hoover's assistant, Clyde Tolson, noted that he couldn't give Mortimer any official information, but advised him how to get it.

The bureau opened its first file on Sinatra in 1943 because Hoover, after receiving a letter from a concerned citizen, became alarmed about the Hitler-like hysteria that the idol had generated among young people. Four years later, the agency began keeping tabs on his associates as a result of the Havana incident of '47. In between, agents investigated charges that the singer had bribed his way out of the draft and was a communist sympathizer, neither of which was true. The FBI accepted the hearsay of "confidential informants" of known and unknown reliability to launch investigations. The bureau also added the sensational journalism of the times to its files. The truth is that young Sinatra was despised by American men of the Second World War. They were the ones fighting in Europe while their girlfriends, wives and sisters were swooning over a skinny millionaire who'd evaded the draft. But the beau of the bobby-soxers was a victim, in this case. The doctor who delivered him, punctured his left eardrum and scarred his neck with forceps. He had chronic mastoiditis. He was emotionally unstable, according to Selective Service records. He was legitimately 4-F.

In 1952, Sinatra issued a more detailed statement about the 1947 Havana incident because Mortimer had launched new accusations, saying the singer brought $2 million in small bills to Luciano in 1947. As evidence, the writer noted that Sinatra was carrying his own bag as he left the plane with the Fischettis.

"Picture me, skinny Frankie, lifting two-million dollars in small bills," Sinatra wrote in the American Weekly, according to Shaw. "…I stepped off the plane in Havana with a small bag in which I carried my oils, sketching material and personal jewelry, which I never send with my regular baggage." He went on to explain that he ran into the Fischettis at a benefit at which he'd performed in Miami, and learned that the brothers were going to be on the same plane to Havana as he. That evening (probably at the Nacional), a large group of people invited him to have dinner. He accepted, and while eating discovered that Luciano was among them.

"After dinner I went to the jai alai games and then, with an acquaintance, toured the night spots," Sinatra wrote. "We finally wound up at the Havana [Gran] Casino [Nacional] where we passed a table at which were Luciano and several other men. They insisted that we sit down and have a drink. Again, rather than cause a disturbance, I had a quick drink and excused myself. These were the only times I've seen Luciano in my life."

Attracted by the glamour associated with gangsters since his boyhood in Hoboken, New Jersey, and apparently not displeased by the dangerous edge they added to his persona, the bad boy didn't mention that he and Hank Sanicola, his manager, had visited Luciano in Naples, Italy, in 1949. Italian police found Sinatra's unlisted telephone number among the mobster's possessions, along with a cigarette case with the inscription: "To my dear pal, Charlie, from his friend Frank Sinatra," according to author Kitty Kelley, who wasn't the first writer to mention the episode. Sinatra's tarnished image makes it difficult for some fans to defend his musical legacy. They find it necessary to separate the music from the man in order to love his work. ("I love his music, not him," they say.)

There's solid ground on which to defend his music, however. Sinatra was like a pit bull with a bone throughout a singing career that undulated with the ebb and flow of American culture. He wouldn't relinquish his determination to turn popular singing into an art. And with the unparalleled musical foundation he built in the Harry James and Dorsey schools of melody between 1939 and 1942, he succeeded like no one else. Maybe that's why his career lasted three generations and his music imprinted itself upon lovers from here to eternity. More than seven years after his death at 82 on May 14, 1998, Sinatra still croons and swings on stereos throughout the country every weekend on Sid Mark's nationally syndicated radio show. "The Sounds of Sinatra" celebrated its 50th anniversary last November 12 at Harrah's Hotel & Casino Concert Center in Atlantic City. Bill Miller, 91, Sinatra's personal pianist from 1951 on, was there, this time accompanying Frank Sinatra Jr. in a 38-piece orchestra playing the legend's music. Miller says that in the 47 years he knew Sinatra, the man never spoke with him about Havana.

But Cuban teenagers still speak about Sinatra. They listen as their grandparents and parents play his LPs and talk about his music in Havana, where he thought he went unnoticed for the most part. However, Havana is where the strains of his various public and private lives still live vividly in the public domain. Sinatra's photos, or photocopies of pictures, can be found at the Hotels Nacional and Capri. A nearly life-size cardboard cutout of him greets diners on the rooftop restaurant of the Hotel Seville, not far from the capitol. Cuba TV occasionally airs his life story. Sinatra is seen by more Habaneros now than when he was there in vivo. No one knows for sure how many times he visited. It could have been five.

Frankie Blue Eyes' final visit to the tropical paradise may have been in January of 1952. He flew there with Cleveland mobster Carmen Piro and met with Luciano, according to the FBI, which, as usual, could not substantiate the information.

By then, too, Las Vegas was blooming with hotel casinos, the colorful characters that created them and hundreds of showgirls. There was no longer any need for the singer to be dancing in the dark in the Cuban capital.

Nevertheless, Jorge Jorge still recounts his recollections of La Voz, and in so doing keeps alive the memory of Sinatra's Havana nights.

Bill "Giullermo" Iezzi is a suburban staff writer for The Philadelphia Inquirer who's been writing stories from Cuba for many years.