Sinatra 'carried millions of dollars through airport customs for Mafia'

Frank Sinatra once came within a hair's breadth of being caught carrying millions of dollars as a Mafia money courier, and had family links with Charles "Lucky" Luciano, according to a new book giving perhaps the most detailed picture yet of the gangland connections of Ol' Blue Eyes.

Frank Sinatra once came within a hair's breadth of being caught carrying millions of dollars as a Mafia money courier, and had family links with Charles "Lucky" Luciano, according to a new book giving perhaps the most detailed picture yet of the gangland connections of Ol' Blue Eyes.

The near arrest, according to the actor Jerry Lewis, a friend of Sinatra, came in 1947 when the singer was going through customs at a New York airport with a briefcase carrying "$3.5m in 50s". Customs officials actually opened the case, but then abandoned the search because of the crowd of people trying to get a glimpse of the star. "Otherwise," Lewis said, "we would never have heard of him again."

The episode is recounted in an unauthorised biography, Sinatra: the Life by Anthony Summers and Robbyn Swan, of which excerpts are published in the latest edition of Vanity Fair magazine. The authors say that Lewis did not see the customs incident in person, but described it as "a fact of which he had knowledge".

Sinatra's association with the Mafia has been the subject of speculation for decades, well before the singer's death in May 1998. Later that year the FBI released a file depicting him as a friend of the Chicago boss Sam Giancana.

The character of Johnny Fontane in the film The Godfather is believed to have been based on Sinatra. In the movie, Fontane is a singer whose faltering career is revived by the mobster Corleone family. The book sayspressure from the Luciano crime syndicate got Sinatrathe part of Private Angelo Maggio in the 1953 film From Here to Eternity, for which he won an Oscar for best supporting actor.

Sinatra always denied any gangland connections, but the book claims that in addition to Giancana, the singer-actor knew both Frank Costello - known to Mafia aficionados as the "Prime Minister" because of his links with politicians, judges and police officials - and Luciano himself, generally considered the most important Italian-American gangster of the mid 20th century.

The book claims that Sinatra's grandfather was born in Lercara Friddi, a small Sicilian town in the Palermo province that was also home town of the Lucianos. The two families apparently knew each other there, before they emigrated to the US.

The young Sinatra grew up in Hoboken, New Jersey during prohibition, when bootlegging was rife and the Mob a constant presence. Later, say the authors, the casual contacts with Mafia figures grew personal.

The account of Sinatra's association with Luciano focuses on a stay in Cuba in early 1947. The singer claimed to have hardly known Luciano. Sinatra once said: "I was brought up to shake a man's hand when I am introduced to him, without first investigating his past," when asked about a reported encounter with the founder of Murder, Incorporated, the assassination arm of the Mafia.

In fact, the two stayed at the same hotel in Havana. The manager of the Hotel Nacional told a reporter at the time that Sinatra "was spending most of his waking hours with Lucky Luciano and an assorted group of gamblers and hoodlums".

The book also suggests that Sinatra took part in a Mafia-organised orgy at the Nacional. A friend of Costello, meanwhile, recounts that Sinatra and Costello were "great pals".

Years later, after Luciano had been expelled from the US and returned to Italy, the two men met in a hotel suite in Rome.

According to George Jacobs, Sinatra's valet, Luciano rose from his chair and kissed the singer. The meeting struck Jacobs as Sinatra's "one joyous moment" of the trip.