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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

Bill "Guillermo" Iezzi
From the Print Edition:
Camilo Villegas, July/August 2006

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.

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