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essentially romantic vision of that world was saved from
     sentimentality by a knowing New York tone. Like Sinatra, he was afflicted by insomnia and bouts of personal loneliness; he
     read widely and intelligently, deep into the night. Sinatra never gave up the whiskey, but he was a reader too; he and Cannon
     talked at all hours of the night about books, and it was Cannon who urged him to read Nelson Algren’s
The Man with the Golden Arm
, which was the basis of one of Sinatra’s finest movies. It didn’t matter where they were staying; insomniacs without wives
     can always be reached by phone.
    Cannon also got Sinatra to read Murray Kempton, who was writing his brilliant column for the
New York Post
in the same years that Cannon was the star of the sports section. Kempton was an absolute original who brought a unique,
     mandarin style to newspapers; on some days it was as if Henry James had agreed to cover the longshoremen’s union. He had an
     extraordinary sympathy for rascals, outcasts, those subjected to lofty moralizing. Nobody ever wrote more intelligently about
     Sinatra than Kempton did in a handful of columns across the years. But Kempton, who also liked his whiskey, was not a man
     who moved easily through the night. It was hard to imagine him sitting around in saloons. But Sinatra loved his work and would
     have his columns (and Cannon’s) airmailed to him each day in California. “The man is a marvel,” he said to me once about Kempton.
     “It’s like listening to Louis Armstrong, or Roy Eldridge: you don’t know where the hell he is going, but somehow he gets there
     and it knocks your socks off.” He made certain that Kempton covered the 1961 inaugural party for John F. Kennedy, which Sinatra
     produced. He joined him occasionally at more formal parties in New York, sometimes at his own apartment on East Seventy-second
     Street, near Third Avenue. He sent him fan mail, which he signed “Francis Albert.” But he didn’t call much on the telephone.
     “Kempton is one of those guys,” he explained, “that makes me feel tongue-tied.”
    I was twenty years younger than Sinatra, but he seemed to be comfortable when I was around. It certainly helped that Cannon
     and Shirley MacLaine had vouched for me, and he was impressed that I knew Kempton. There might have been one other factor:
     Cannon and I were both high school dropouts, as was Sinatra. (Oddly, Cannon and I had dropped out of the same institution,
     a great Jesuit high school called Regis.) This might have meant more to Sinatra than it did to us; in a very important way
     he defined success as a triumph over the odds.
    “Every time they print your column,” he said to me once, “you are getting your fucking diploma.”
    I laughed. But he was serious.
    Later, Sinatra had one other newspaper friend, Sidney Zion, now a fine columnist for the
New York Daily News
. Zion came out of Paterson, New Jersey, went to law school, worked as a prosecutor, and then became a reporter for the
New York Post
. Like all of us at the paper, he worshiped Kempton. But he had been shaped by the traditions and lore of urban New Jersey.
     The figure of Frank Sinatra was an immense part of that tradition. Zion loved the music that Sinatra loved most, the music
     of the hours after midnight. He loved saloons. He loved smoking and drinking (and still does). He is a wonderful storyteller.
    “I got to know him around 1980, the time of the
Trilogy
album,” Zion told me. “I did a piece about the old music for the
Times
, and one thing led to another. A mutual friend introduced us, and I’d see him when he was in New York. I think he liked me
     because he’d never met a Jew who drank as much as I did.”
    Sinatra was always more cynical about the Hollywood press corps. He thought most of them were freeloaders, or on the take.
     “I’ve seen the bills, baby,” he said once about reporters and columnists who took money from the publicity budgets of the
     studios. In