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SINATRA TOURED THE world, giving concerts. He devoted the proceeds of some tours entirely to charitable causes. He gave large sums away. He would pick up the hospital bills of an actor friend in need—Lee J. Cobb, for example, when he had a heart attack in June 1955—and expected nothing in return. He was spontaneous. Once, on a visit to Gregory Peck’s place, he saw an empty wall in the foyer. “You need a painting there, and I know just the one,” he said. He went home and painted an abstract canvas for the spot.

Sinatra tipped (he called it “duking”) more lavishly than anyone else. On the evening news if he saw some poor fellow whose house was damaged in a landslide, he might turn to an associate and say “Send him a nickel,” meaning five hundred dollars. Every so often, when Sinatra did something stupid in public—throw a drunken tantrum, humiliate a reporter, make like an asshole—the fact would be reported to me, a known enthusiast, and one time I conceded the point but added that there were things he didn’t get credit for: his many unsolicited acts of generosity and charity. Once, when I went into this rap with my wife, Stacey deadpanned: “Poor Frank.”

After Sinatra died, on May 14, 1998, everyone quoted Dean Martin: “It’s Frank’s world, we’re just living in it.” When I told a friend, a very attractive and flirtatious woman of twenty-six, that I was working on a Sinatra obit, she said, “Is there a place in it for a photograph of me naked surrounded by Frank Sinatra CDs?”

The photo that dogged him for decades: Frank with Carlo Gambino and associates, 1970s.
Fred R. Conrad / Getty Images