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But the facts indicate that he did know some shady people. He was friendly with Jersey hoodlum Willie Moretti until the syphilitic gangster was shot to death. He was friendly with Joseph “Joe Fisher” Fischetti, traveled with him to Havana in 1947, where he spent time with Lucky Luciano. A nineteen-page Justice Department memorandum prepared in 1962 said that its surveillance placed Sinatra in contact with about ten of the country’s top hoodlums. Some had Sinatra’s unlisted number. He did favors for others.

“I was brought up to shake a man’s hand when I am introduced to him, without first investigating his past,” Sinatra said huffily during the Luciano uproar. The same could be said about the scandal over the photograph taken a few years ago with mob boss Carlo Gambino, backstage at the Westchester Premier Theater. More serious questions have now been raised about Sinatra and that same theater.

A federal grand jury is investigating whether Sinatra, his lawyer Mickey Rudin, and Jilly Rizzo took $50,000 under the table during a May 1977 gig there. Court papers filed by prosecutor Nathaniel Akerman said that the possible Sinatra connection arose during the trial of one Louis “Lewie Dome” Pacella, supposedly a friend of Sinatra’s. The court papers state: “The grand jury’s investigation was based in part on evidence introduced at Pacella’s trial, which showed that in addition to Pacella, other individuals close to Frank Sinatra had received monies illegally…” Once again, Sinatra is afloat on that dark underground river.

“Did I know those guys?” he said to me once. “Sure, I knew some of those guys. I spent a lot of time working in saloons. And saloons are not run by the Christian Brothers. There were a lot of guys around, and they came out of Prohibition, and they ran pretty good saloons. I was a kid. I worked in the places that were open. They paid you, and the checks didn’t bounce. I didn’t meet any Nobel Prize winners in saloons. But if Francis of Assisi was a singer and worked in saloons, he would’ye met the same guys. That doesn’t make him part of something. They said hello, you said hello. They came backstage. They thanked you. You offered them a drink. That was it.”

He paused. “And it doesn’t matter anymore, does it? Most of the guys I knew, or met, are dead.”

One of them was Salvatore Giancana, sometimes known as Momo, or Mooney. A graduate of Joliet prison, he ducked World War II by doing a crazy act for the draft board, which labeled him “a constitutional psychopath.” He rose through the wartime rackets to the leadership of the Chicago mob in the 1950s. During that period he and Sinatra became friends and were seen in various places together. The star-struck Momo later began a long love affair with singer Phyllis McGuire, and the friendship deepened. In 1962 Sinatra, Dean Martin, and Sammy Davis played a special engagement at a Giancana joint called the Villa Venice, northwest of Chicago. When the FBI questioned the performers, Sinatra said he did it for a boyhood friend named Leo Olsen, who fronted the place for Momo. Sammy Davis was more to the point.

“Baby, let me say this,” he told an FBI man. “I got one eye, and that one eye sees a lot of things that my brain tells me I shouldn’t talk about. Because my brain says that if I do, my one eye might not be seeing anything after a while.”

Sinatra’s friendship with Sam Giancana was most severely tested in 1963, when the Nevada Gaming Control Board charged that the Chicago hoodlum had been a week-long guest at Sinatra’s Cal-Neva Lodge in Lake Tahoe. His mere presence was enough to revoke the casino’s gambling license, and Sinatra first said he would fight the charge. When Edward A. Olsen, then chairman of the gambling board, said that he didn’t want to talk to Sinatra until he subpoenaed him, Olsen claims Sinatra shouted over the phone, “You subpoena me and you’re going to get a big, fat, f surprise.”

But when the crunch came two weeks later, Sinatra chose not to fight the revocation order. Apparently his friendship with Giancana was more important than his investment in Nevada, and he sold his interests for $3.5 million. In 1975 Giancana was shot to death in the basement of his Chicago home. Phyllis McGuire went to the funeral, but Sinatra didn’t. Sinatra is again trying to get a gambling license in Nevada.

“It’s ridiculous to think Sinatra’s in the mob,” said one New Yorker who has watched gangsters collect around Sinatra for more than 30 years. “He’s too visible. He’s too hot. But he likes them. He thinks they’re funny. In some way he admires them. For him it’s like they were characters in some movie.”