Sinatra

by James Kaplan

Giancana himself admitted as much. He once told a Chicago associate named Tommy DiBella that he’d considered putting out a contract on Sinatra until one night, when he was in bed with his lady friend Phyllis McGuire, a revelation came to him: “I’m fucking Phyllis, playing Sinatra songs in the background, and the whole time I’m thinking to myself, Christ, how can I silence that voice? It’s the most beautiful sound in the world. Frank’s lucky he’s got it. It saved his life.”

  Frank knew it. And so he could continue to rub shoulders with Giancana and other hoodlums, doing small favors for them when it was convenient and doing nothing for them if he preferred. Sinatra’s relationship with the Mob was a transaction, conducted in the counterfeit currency of the underworld: the gangsters got to bask in his aura, and he in theirs; each side pretended to do things for the other, and neither did much.

  But in both worlds, show business and the crime business, illusion was powerful. If people were scared of Frank because they thought he was mobbed up, he didn’t mind a bit. He got to take on his friends’ power without paying for it.

  So he thought, at least.

  —

  Ava blew into New York again at the end of September. At almost thirty-nine, she was increasingly sensitive about her looks, if not appearances: one night she walked into the Chateau Madrid with a boy toy—a twenty-four-year-old named Guy Pastor, a son of the bandleader Tony Pastor—and promptly walked out when a flamenco dancer named Raul started taking snapshots in her general direction. She returned only after being persuaded that the dancer was photographing the floor show, not her. Frank was also in town, having bibulous fun with a posse that included Joe E. Lewis. Ava tried phoning him but missed him; he called back but missed her. Finally, they made contact and, a couple of nights later, went out—in a group that included the Porfirio Rubirosas, the George Axelrods, and Mrs. Mike Romanoff.

  “About 1 a.m., Frank and Ava parted,” Earl Wilson noted. “Frank took a taxi to El Morocco, and Ava went off somewhere by limousine.

  “A photographer who earlier asked to take a picture of Frank and Ava was told: No, they were merely part of a group.”

  No doubt he was told more emphatically than that, but it was true.

  —

  In a mid-October Voice of Broadway column, Dorothy Kilgallen wrote that she had received many letters like the following:

  Dear Miss Kilgallen:

  I would find my day lost if I missed your column in the Evening Journal, therefore I would like your opinion (according to the papers) why the President and his charming wife would entertain a person such as Frank Sinatra at their home, while the President’s brother, Robert Kennedy, is supposed to be going to investigate Sinatra’s friends the Fischettis. I can assure you that in my family there were more than 50 votes cast for the President, but from now on not one vote will be given to any of the Kennedys, and believe me there are more like my family who are disgusted with the President’s choice of friends. May you and yours enjoy the best of health, and God bless you.

  Sincerely,

  Mary Ann Nolan

  Kilgallen replied, in part:

  Miss Nolan, you and all the others who wrote to me are an admirable but naïve minority. The majority of people in this country admire—openly or secretly—a successful tough guy who refers to women as “broads” and gets off airplanes with a drink of whisky in his hand. I suppose a parlor psychiatrist would deduce there are a great many conforming Milquetoasts in this land who would give anything to cut loose from the wife and kids and the mortgage and community mores and live in the Sinatra fashion, no rules and plenty of booze and a girl anywhere you look.

  In any case, next to President Kennedy Frank Sinatra is the biggest man in America today. He is rich, powerful and adored by millions of fans. He is more famous than any writer, philosopher, clergyman or poet. If you don’t believe me walk down your own street and ask the first 50 people you meet who is the author of the last Pulitzer Prize novel. Ask them who is Bertrand Russell. Ask them to name the present Archbishop of Canterbury. Ask them what Robert Frost does for a living. You’ll be surprised at the blank looks.

  But ask them who Frank Sinatra is and you’ll get 50 right answers.

  So why shouldn’t President Kennedy entertain him, if he wants to? The election is over. He won it.

  —

  He returned to the Sands at the beginning of November for a two-week stand; as always, he was a smash. Among those attending his sold-out premiere were the ubiquitous Porfirio Rubirosas, along with the Sammy Davises, Mike and Gloria Romanoff, Vic Damone, Richard Conte, Leo Durocher, and Tommy Sands. Frank drew a big ovation when he introduced a surprise guest. “Here’s the mother of my children,” he said, indicating Big Nancy, who sat ringside.

  Also present was a Reprise engineer: Sinatra was having the concerts (with Antonio Morelli conducting a twenty-four-piece orchestra, including Bill Miller on the piano) recorded, intending to make his first live album, a prospect that thrilled his most ardent fans, especially those who hadn’t had a chance to see him in person. Frank’s label taped nine of the shows from that Sands stand, and, according to Ed O’Brien, he considered “a lot of the songs from each show” good enough to be mastered. “Frank was very excited about a live set coming out on Reprise,” O’Brien said. The tapes were stored at Reprise headquarters in Los Angeles, and then the relentless rush of Sinatra’s life swept on.

  The first item on the agenda was recording a new album—his sixth since the previous December.

  He had been astoundingly productive during Reprise’s first twelve months. As Friedwald writes, “The Chairman had made two full-length sets with Billy May, done two albums with collaborators so old that they were spanking new [Stordahl and Oliver], and done one uptempo set with a younger arranger with whom he’d never worked before [Johnny Mandel]. The only gap left to fill was to do the same with a ballad album. That would be Sinatra and Strings, his first of many projects with Don Costa, a fast-rising and extremely talented orchestrator and producer.”

  Costa, thirty-six, was a musical jack-of-all-trades: “a musician’s musician; an arranger’s arranger,” the arranger-songwriter Mickey Leonard said. He was a superb guitarist who’d made hit instrumental recordings; a brilliant, lightning-fast (and self-taught) orchestrator who’d lately been writing successfully for Steve Lawrence and Eydie Gorme; and, recently as well, the A&R man, chief arranger, and producer for Steve and Eydie’s label, ABC-Paramount Records. He was also a legendary character: charming, disorganized, perpetually overcommitted, and always running late, in no small part thanks to his fondness for alcohol and late-night fun. The studio engineer Lee Herschberg remembered Costa, over many glasses of wine, thinking of a song idea, scribbling out the beginning of an arrangement on a restaurant tablecloth, then taking the tablecloth back to his hotel, staying up all night to complete a chart for full orchestra, and recording the tune the next day.

  “Costa could write an intro that they could make a symphony out of,” said the violinist Carmel Malin. “He’d write these chords that were quite intricate, and they’d say, ‘That note isn’t right.’ He said, ‘That note is right.’ You’d play it again, and it was right. He said, ‘Don’t you ever listen to Ravel?’ ”

  Of course there was another arranger who had listened to a good deal of Ravel, but Nelson Riddle, still at Capitol, remained contractually unavailable to Reprise—a fact that didn’t prevent him from being “extremely upset” by Frank’s decision to hire Costa, Peter Levinson writes. “As a result, he began to refer to Costa as ‘Don Co-Star,’ a term which indicated more than a touch of envy.”

  And also a grain of truth. As impressive as Costa’s gifts were, commentators rarely assign him to the first rank of Sinatra’s arrangers. “Don Costa was a great pinch hitter,” Charles Granata writes. “He was the guy you called in when you needed someone else’s sound, but that someone else wasn’t available.”

  “Do you know who Don Costa really was all the time to Frank?” Sammy Cahn
asked Will Friedwald. “Don Costa was Axel all over again, with those deeper, fuller strings.”

  Perhaps. And perhaps Costa’s chameleonic qualities ever so slightly diminished him in Sinatra’s eyes. As we’ve seen, every artistic relationship in Frank’s life was also an intricate power struggle: he could run roughshod over any collaborator who betrayed the slightest weakness, and in years to come, he would dominate Costa, to their mutual detriment. Theirs was a partnership that began at its peak. “Sinatra and Strings,” the arranger said in the 1970s, “was, and always will be, the hallmark of my existence.”

  There was another classical composer besides Ravel to whom Costa’s beautiful work on this album has a kinship. A key lies in something else Mickey Leonard said: “Don Costa was among the most emotional writers, and his orchestrations are very theatrical. He wrote with a great sense of drama.”

  The words also describe Giacomo Puccini, a particular favorite of Frank’s. The opera that was his life was now deep into its second act, and he wanted a means to express it.

  “Sinatra and Strings opened up a whole new era,” Frank Sinatra Jr. told Granata. “The orchestras were getting bigger, and Pop wanted that lush string sound.”

  They did it right. In the deep flow and shimmer of its arrangements and the magnificent ardor of Frank’s vocals (just listen to his “Stardust” here—he only sings the verse!—or his “Night and Day”), Sinatra & Strings is unapologetically emotional and artistically superlative. Puccini would have approved.

  —

  At the end of November, Frank headed back to Australia for four nights of concerts in Sydney (to the tune of $100,000), to be followed by a jaunt to Hong Kong, Tokyo, and Thailand. An odd crew accompanied him: the pianist Bill Miller, the trumpet player Al Porcino, and the drummer Johnny Markham (they would work with local musicians in Sydney); Dorothy Provine; Leo Durocher; Mike and Gloria Romanoff; and a New York barkeep named Ermenegildo Rizzo—Jilly.

  Jilly Rizzo was a character—Frank’s kind of character: a knockabout New York guy who’d grown up in Greenwich Village, gone to war, then worked as a loading-dock laborer and bar bouncer before graduating to bar ownership himself, on West Forty-ninth Street in 1948. Though he’d never been a boxer, he had a detached retina (suffered as the result of horseplay with his brother and a paper clip, not in the ring) that gave him that look, and he was handy with his fists. (He also liked to carry a blackjack up his sleeve, for insurance.) He had never been a wiseguy, but he’d worked for them and palled around with them and could talk the talk. In 1954, he bought a new bar, in the north of the theater district at 256 West Fifty-second Street, and gave the place his own melodic first name.

  Jilly’s was a long, cozily dim space, a couple of steps down from street level, with a lengthy, beautiful oak bar on the right as you entered, a piano bar in the back, and a predominantly red decor. Nothing fancy; lots of smoke and laughs. It had, George Jacobs recalled, “one unusual distinction: it served Chinese food, perhaps the worst Chinese food in New York. New Jersey–style Chinese food, chicken chow mein, moo goo gai pan, sweet and sour pork, totally inauthentic and not even tasty as fake food. Mr. S thought it was magnificent, the franks and beans of the mysterious East.”

  Frank began gravitating there in the mid-1950s, after first gravitating to Jilly himself, in an incident that carries the nimbus of mythology.

  As one of Rizzo’s sons explained it,

  There was a beef in one of the clubs where my father used to be the bouncer, when he had his bouncing jobs all over town. There was a big argument, and they couldn’t handle this guy who had come into the joint, so they called my father and said, “We need you over here.”

  My father said, “I’ll be right there,” and Frank was in there that night. My father went in, gave the guy one, two, three—gone—and Frank said, “I gotta meet this guy.” That’s how it started.

  The two of them became closer in Miami in November 1958, while Frank was shooting A Hole in the Head. Rizzo was there with his singular houseboat; let Earl Wilson describe it, in an item datelined Miami Beach:

  A remarkable Chinese houseboat—modern design, worth $140,000, which must be towed as it has no motors—is docked here, the property of Jilly Rizzo, owner of the NY pub, “Jilly’s.” The boat (“Jilly’s Yen”), docked across from the Eden Roc, has a round bed and gold bathroom fixtures—and you have to take your shoes off when you enter.

  Everything about Jilly was unabashedly just the way it was, from his speech, which was full of malapropisms and double negatives, to his wife, Sorrel “Honey” King, whose unusual hair tint inspired Frank to dub her “the blue Jew.” Rizzo was in some ways the kind of man Sinatra wished he had been: brave and tough and funny and apparently entirely without inner demons of any sort. And not impressed by much, including, at times, Frank himself, whom he called “the singer.” Sycophants were easy to come by; Jilly was warm and loyal, but he went his own way. As a friend put it,

  Jilly was successful before he met Frank Sinatra. He had a very successful business, and he was just an attraction for people. A Who’s Who of people went to Jilly’s, before or after the theater. And when you went to Jilly’s, you had nothing to worry about, because you were well protected.

  “One night, somebody at the bar stole a woman’s purse, and the word got back to him,” recalled the pianist Monty Alexander, who began playing at Jilly’s in the early 1960s. “Within no time, Jilly grabbed the guy, dragged him to the subway station and threw him down the stairs, [saying,] ‘You don’t come in my club doing this.’ Jilly himself. He didn’t have the bouncer do it.”

  Soon Sinatra and Rizzo began spending more time together. Jilly was someone he could talk to, someone he didn’t have to watch his p’s and q’s with, and if need be, someone who could step in if trouble arose. (He also was not a drinker, which meant he was alert when trouble arose.)

  And he was amusing company. As were Durocher and Mike Romanoff. The Sydney concerts went well, but the sightseeing afterward was shadowed by the gloom of the king. In spite of many amusements—in Thailand, the maharaja of Jaipur escorted Sinatra and company through his private zoo, racetrack, and golf course—Frank’s “agonizing loneliness” on the tour “made up his mind to marry again,” according to “a pal who made the trip to Australia with the star” (Durocher? Romanoff? certainly not Jilly) who spoke to Walter Winchell. Winchell wrote,

  Dorothy Provine, one of the cast, was written up in some columns as being his latest diversion, but the fact is that Sinatra spent most of his time alone in his hotel room brooding. He kept phoning Juliet Prowse, trying to persuade her to “take the first jet and please come see me. I miss you terribly.” “Frank,” she is said to have told him. “I don’t want to be on your girl list. It can only be one way for us!”

  Relating this phone call to the pal, Sinatra pounded a fist on the table, exclaiming: “That’s my kind of Doll!”

  The Sinatra-Prowse relationship was a puzzlement to everyone, probably including Frank and Juliet themselves. She was determined, throughout their relationship, to maintain her independence and to keep working: this was problematic for Sinatra, who was captivated by independent women but didn’t want them to stay that way. (And, naturally, got bored the moment a woman became dependent.)

  They’d been on and off throughout 1961, mostly off. That fall, she told a reporter that their relationship was “serious inasmuch as I was very fond of him and still am. But how long can something go on without any ultimate goal?” When Frank failed to rise to the bait—if bait it was—she told another writer, “I go my way and he goes his. I have my life to lead and I’m not going to sit around. If I want to go out with someone else, I go out. No strings.”

  She meant it. She had a new manager, a handsome young fellow named Eddie Goldstone, and it soon became apparent to the world that he was more than her manager. The gossip columns eagerly charted the pair’s appearances at restaurants and nightclubs on both coasts, breathlessly wondering if you-know-who was
jealous. Sinatra’s old nemesis Lee Mortimer claimed that Frank had had the pair tailed by a private detective, had had “friends” try “to induce [Goldstone] to lay off,” and had threatened him personally. Though Mortimer was a pest and a scold, it was all too easy to believe.

  In the meantime, Goldstone kept Prowse busy professionally as well. Though she’d turned down a second movie with Elvis, she played the lead or second lead in three movies released that year and did a lot of dancing on television. She also performed the title role in a Las Vegas production of Irma la Douce and then, in late December, traveled to New York to do a $10,000 guest spot on The Perry Como Show. Earl Wilson, whom Sinatra read religiously, wrote that he’d “got excited seeing attractive Juliet Prowse at the Copa with a young guy; turned out to be her mgr., Eddie Goldstone.” Frank wouldn’t have been pleased.

  —

  On December 19, Joseph P. Kennedy, seventy-three, suffered a stroke while playing golf in Palm Beach. He would survive for almost eight more years, outliving both his older sons. Confined to a wheelchair, apparently intact mentally—“soaking it all up with those cold blue eyes,” as the chauffeur Frank Saunders recalled—Kennedy was able to utter only one word: no. “Only he did not speak it,” Saunders wrote.

  He made a noise out of it. A long, loud no. NNNnnnooooo! Over and over again. Sometimes he could squeak a yes, and sometimes he’d use his good left hand and arm to make gestures and motion us. He tried to write with his left hand, to give us instructions and tell us what he wanted, but it frustrated him. I would see this look of fear creep into his eyes, and at times there would be something more fleeting in his eyes too—the look you can get from a wild caged animal. He was trapped, and he knew it.

  The description is pitiless, but then there were few people to pity Joe Kennedy. “I was surprised that a man who had been so powerful and was so rich did not have more close friends,” Saunders said. On the short list of those who visited the Ambassador in the weeks and months after he was felled, Frank Sinatra’s name does not appear.