“It was Sinatra who triangulated Hollywood, Washington, and the Mafia” (Wolcott). His Rat Pack pal Lawford, the British-born actor who had married President Kennedy’s sister Pat, introduced Sinatra to Sen. John F. Kennedy in the late 1950s. Like the singer, the senator enjoyed partying in Las Vegas casinos. Following one of his performances at the Sands, Sinatra introduced the by then presidential candidate John Kennedy to Judith Campbell. It happened during the period of the filming of Ocean’s Eleven , the quintessential Rat Pack movie. Sinatra arranged a roomservice lunch for Kennedy and Campbell in his private suite. And thus began a two-year affair that continued after Kennedy occupied the White House and despite the President’s awareness that Campbell had become the mobster Sam Giancana’s moll. All this we know from FBI files, which Sinatra obtained in 1981 under the Freedom of Information Act and which were edited for book publication under the title The Sinatra Files by journalists Tom and Phil Koons in 2000.

He put all the misery of his relationship with Gardner into “I’m a Fool to Want You.”

Giancana and his associates thought they had a line into the White House. They expected that the Kennedy administration would, in exchange for electionyear favors, go easy on Mob activities. They hadn’t reckoned on Robert F. Kennedy’s righteous moral indignation, which took the form of the Attorney General’s holy crusade against organized crime. Besides hating the brothers Kennedy, Giancana was furious with Sinatra (whom he called “the canary") for failing to exercise his supposed influence with the young President. Federal wiretaps caught a conversation between Giancana and Johnny Formosa, a henchman. “Let’s hit Sinatra,” Formosa said. “Or I could whack out a couple of those other guys, Lawford and that [Dean] Martin, and I could take the nigger [Sammy Davis, Jr.] and put his other eye out.” It is said that Giancana decided against whacking the canary because he wanted to hear him sing “Chicago” one more time.

It is difficult to write about Sinatra not only because a million other guys have the same ambition and gallons of ink have already been spilled but because he was more than a singer. What he stands for is complicated: a charmed life, maybe; stylishness; his ability to put over a song, to make it seem like an extension of his own personality and experience; the fascination of an intense and contradictory personality, the self-described "18-karat manic-depressive,” a wounded swinger who could consort with Presidents and gangsters, but who also liked painting and took photographs at the first Ali-Frazier fight that were good enough for Life magazine to run. The trajectory of his career extended from Roosevelt to Reagan, from the Big Band era that he helped bring to an end by going solo successfully in 1942 to beyond the boozy Las Vegas casino scene of the go-go 1960s. He went nightclubbing with JFK, performed at the Nixon White House, took tea with Nancy Reagan when her husband was President. He had also participated in the common citizen’s love of FDR. (In the version of the great Vernon Duke-Ira Gershwin standard “I Can’t Get Started” that he sings on the album No One Cares , in which the speaker’s worldly success is contrasted with his failure to win the girl, Sinatra sings this marvelous couplet: “Each time I chanced to see Franklin D. / He always said ‘Hi, buddy,’ to me"). Nancy Sinatra, with whom he sang the forgettable topof-the-charts hit “Somethin’ Stupid” in the late 1960s, said that trying to define her father was like trying to analyze electricity. He had a flair for the dramatic and an instinct for stage center. A fingersnapping Lazarus in a tux, he took a punch, went down, and then got back on his feet and won the fight.

In the 1940s Sinatra had hit record after hit record. He liked the taste of Hollywood glamour and learned to dance well enough to serve as Gene Kelly’s junior partner in sailor-suit movies like On the Town and Anchors Aweigh . And then his career came crashing down. He was photographed with gangsters in Havana in February 1947. He punched out the obnoxious Hearst columnist Lee Mortimer in April 1947 and did other things that earned him the enmity of the fourth estate. He conducted a very public love affair with Ava Gardner, then possibly the most beautiful woman in Hollywood. She and Sinatra fought constantly, histrionically. Female fans deserted him just as he had deserted his wife and children. He would lose his radio show, would jeopardize his recording contract with Columbia. In 1950 his voice failed him in public; he opened the mouth to sing and nothing came out. He was told that he suffered from vocal cord strain and that the only way to get better was not to sing.

For Ava Gardner, the love of his life, Sinatra was willing to risk everything. The affair wrecked his marriage, his health, and his reputation. There are photographs of him with Ava that make it seem they are having the time of their lives. They married in 1951, but it was no honeymoon. Yet the couple’s bitter quarrels seem to have added to the sexual intensity of the relationship.