PICTURE WORTH A THOUSAND IMPLICATIONS

Sinatra never denied his presence in Cuba, yet the photos instigated decades of conjecture and allegations

When the crooner landed in Havana on 11 February 1947, a newsreel team happened to be there too. A still frame shows (according to government agents at the time) Sinatra situated near Chicago gangsters Joe and Rocco Fischetti (a third Fischetti, Charlie, was also on the flight). That image furthered suspicion and narratives formulated by unfriendly columnists and agents of the FBI and Narcotics Bureau. Sinatra already bore bad blood with some gossip columnists, but the Feds to that point only had him on radar for reasons relating to the ‘red scare’ (communist rhetoric). Everything changed quickly when American writer Robert Ruark outed Lucky Luciano’s presence in Havana and implied Sinatra and the kingpin were pals. If the primary target of Ruark’s war of attrition was Luciano, with Sinatra secondary, then columnist Lee Mortimer’s was the flip side. He upped the ante against the singer by suggesting to government contacts that Sinatra’s carry-on bag (seen in the photo) was packed with a $2,000,000 gift for Luciano. Sinatra tried feverishly to douse the flames of PR hell, but it didn’t help when he slugged Mortimer in a New York club two months later.

Both Sinatra and Luciano vehemently denied they ever knew each other prior to a ‘chance’ meeting in Cuba, but when Senator Estes Kefauver set his sights on American organised crime in the 1950s the infamous photo reappeared publicly, while a handful of ‘other’ photos were presented to Sinatra, allegedly depicting him hobnobbing with Luciano, the Fischettis and other ‘known’ gangsters. Interestingly, at least one of the purported photos disappeared. According to a 1962 FBI memo, “A photograph of Sinatra taken with two of the leading gangsters in this country was stolen from the files of the Kefauver Crime Investigation Committee not too long ago.”