Rat Pack Confidential

by Shawn Levy

  In some respects, Giancana was a typically ruthless mobster who rose to the top out of sheer guts, greed, and callousness. He’d been born in 1908 in the Patch, a dirt-poor Italo-American ghetto in Chicago, and he’d run from his early youth with a gang called the 42s, a bunch of geniuses who’d misremembered the number of men in Ali Baba’s fabled crew when naming themselves. The 42s stole and raped and beat and extorted and, when they needed to cover up those trespasses, they bombed and killed. They were keen on automobiles: They stole ’em, they joyrode in ’em, they outran the cops in ’em. Giancana, whose lunatic antics so surpassed those of his hoodlum friends that he got the nickname Mooney, which was itself shortened to ‘Mo’ or ‘Momo,’ was the best wheelman in the gang; he was involved in business well beyond his years simply because he could be counted on to bring everybody back from it untouched.

  Giancana’s way with a car got him noticed by the big mobs in town; before long he was driving for Machine Gun Jack McGurn, one of Al Capone’s most feared henchmen. Service to McGurn meant Giancana met the other powers who’d succeeded Capone: Charlie Fischetti, Tony Accardo, Jake Guzik, Frank Nitti, Paul Ricca. In time, with enough bodies in his wake and enough rackets under his iron-fisted control, he became their peer and successor.

  By the fifties, his reputation as a killer and earner put him on top. Among his coups: commandeering Chicago’s numbers rackets from black gamblers, spreading the gambling interests of the Chicago mob throughout the Midwest and into Las Vegas, diversifying into businesses like shrimp fishing in the Caribbean and semilegitimate concerns as far-flung as Mexico, South America, and Iran. He was, friends of Giancana’s liked to quote Meyer Lansky as saying, “the only Italian who handles money like a Jew.” He carried a business card that read:

  On the back was a carefully worded script: “Under the Fifth Amendment to the Constitution of The United States, I respectfully decline to answer, on the grounds that my answer may tend to incriminate me”: a real character.

  For all his ferocity, Giancana was strangely domestic and even dainty. Tony Accardo, his predecessor on top of the Chicago Outfit, was known as Joe Batters in recognition of his use of a Louisville Slugger as an instrument of negotiation; he chopped wood and mowed his lawn to let off steam. Giancana, on the contrary, collected Dresden figurines, sterling tea services, oil paintings. His suburban Chicago home was stuffed with fine antiques and rugs—a Louis XV mahogany piano was the centerpiece—and whole sets of Meissen china. He golfed—his backyard was mown exactingly into a putting surface—and he loved to shop for jewelry, in which he had understated, discriminating taste—no gaudy pinky rings for him.

  Well, there was one pinky ring, a star sapphire friendship ring given to Giancana by the only one of his many Hollywood acquaintances he could stand: Frank Sinatra.

  Giancana flat out used just about every big star who came his way. He was contemptuous of anyone who made a gaudy living yet still had money troubles, as did so many celebrities he’d met. “Don’t ever be star-struck by all that movie baloney,” he told his half brother. “They’re all worthless bums and whores.” Yet still he was drawn to their company—maybe more than was smart. His open affair with singer Phyllis McGuire put him in the newspapers and made his more discreet mob partners worry, and rightly so, since it made him an easier target for the feds; he carried on with singer Keely Smith and bragged to his half brother about schtupping Marilyn Monroe and lesser Hollywood lights. For male stars he had almost no use at all, but in Sinatra he felt he’d found a man’s man, a guy who had real class and knew how to party, a diamond, he assured those around him, amid the dross of Hollywood.

  Their friendship went back to the fifties, when Giancana staged charity benefits in Chicago as a sop to his patient, sickly little wife. Big guns turned out: Dean and Jerry, Tony Bennett, Bob Hope, Jimmy Durante—filling Chicago Stadium every summer for some rinky-dink Catholic charity that no one had ever heard of. Frank met Giancana through his appearances at these events, and, as was his wont, he courted the don. They hit it off; when Giancana was arrested on a forged driver’s license rap in 1958, cops found Frank’s private phone number in his wallet.

  The gangster and the singer were together frequently throughout the early sixties. They golfed and partied in California, Nevada, Chicago, Miami and Hawaii; they spent Easter together in Palm Springs and dropped in for dinner with Frank’s parents in New Jersey; Giancana visited the Madison, Indiana, set of Some Came Running and was a permanent fixture on the set of Come Blow Your Horn, in which Frank had given Phyllis McGuire a small part.

  The Hollywood crowd around Frank was appalled by the relationship. Giancana was, Peter Lawford said, “really an awful guy with a gargoyle face and weasel nose. I couldn’t stand him, but Frank idolized him because he was the Mafia’s top gun. Frank loved to talk about ‘hits’ and guys getting ‘rubbed out.’ And you better believe that when the word got out around town that Frank was a pal of Sam Giancana, nobody but nobody ever messed with Frank Sinatra. They were too scared. Concrete boots were no joke with this guy. He was a killer.”

  Nobody in showbiz read it right. To them, Frank was a mob intimate. But to those around Giancana, Frank’s solicitude was an embarrassment and a joke. In March 1961, Giancana was in Miami for the Floyd Patterson-Ingemar Johannson heavyweight championship fight—as well as a series of meetings with Johnny Rosselli and intelligence agent Robert Maheu at which plans to assassinate Fidel Castro were discussed. They stayed at the Fontainebleau, and Frank happened to be playing at the hotel; he called Giancana’s room constantly, trying to arrange a visit. Giancana stalled, mocking the singer to his cohorts. Finally, though, he agreed to meet Frank for a drink, telling the others, “We’re going to have to see him sometime. Might as well get it over with now, but watch what you say because the guy’s got a big mouth.”

  In the bar, Frank shook Giancana’s hand. “I see you’re wearing the ring,” he said.

  Giancana said he always wore the token of Frank’s friendship, but Frank wouldn’t believe him: “Oh, no you don’t,” he said. “I heard you hadn’t been wearing the ring. I heard you never wore it.”

  Joseph Shimon, one of Maheu’s operatives, was also at the bar, and he couldn’t believe what he was hearing. “It seemed so ridiculous to me,” he remembered. “He was talking like some frustrated little girl with a broken heart. Finally, I couldn’t help it. I said, ‘What is this? Are you two bastards queer for each other or what?’ Sam fell off his chair laughing, but Sinatra was very embarrassed and turned his back on me.”

  In Ciro’s, Shimon might’ve wound up, like Lee Mortimer, on his ass.

  In front of Giancana, Frank, worried that he might louse up a big connection, was the one too afraid to talk.

  The place was on fire

  Miami was one of their playgrounds, and like everything else they touched then, it was golden.

  The late fifties found the city in the midst of a boom the likes of which it hadn’t experienced in thirty years. Air travel had made south Florida accessible to New Yorkers for quick weekends; Frank virtually advertised it, standing on a tarmac on the cover of Come Fly with Me, one thumb jauntily arched toward the TWA jetliner behind him. With Havana, once the East’s premier party spot, closed by revolution, Miami offered an unrivaled brew of flesh, surf, sun, and elegance—there weren’t casinos, true, but you could drink the water.

  Like Vegas, Miami had a strip of fabulous hotels—the Eden Roc, the Diplomat, and, especially, the Fontainebleau, the gaudy Moderne pipe dream of architect Morris Lapidus, the most expensive, expansive, and exciting jewel of the city’s glittering string. The Fontainebleau catered to the biggest shots and had the biggest stars under contract, the Sands of Collins Avenue. It was the luxe of the luxe in a town that specialized—perhaps, in the absence of legalized gambling, even more than Vegas—in spoiling guests.

  It was also a celebrity magnet, its clubs and hotels offering high fees and, like Vegas, a place for entertainers to relax and watc
h one another work. In January I960, for instance, just as Dean was making a resort movie at the Sands with Frank and the rest of them, Jerry Lewis directed himself in a film at the Fontainebleau, The Bellboy. Two months later, when Ocean’s Eleven wrapped, Dean, Peter, Sammy, and Joey descended on the hotel, where Frank was nearing the end of an engagement. The five of them extended the Summit with a few nights of wild, improvised shows and another big-time production, not a film this time but a truly special special for TV. (Sammy was, at the time, under contract to the rival Eden Roc, but Frank convinced his bosses to free him up for the shows by agreeing to dine at the Eden Roc—along with all his chums—and create publicity for it throughout the week.)

  Frank had scored a coup, perhaps the only one in all of showbiz capable of even equaling the shows at the Sands and the impending release of Ocean’s Eleven: He had secured rights to the first post-army performance of Elvis Presley, an hour-long special for ABC to be shot in Florida with him and various of his cronies. Elvis would only appear twice, briefly, but it was a hugely anticipated pop moment.

  At first blush, it was a quixotic thing for either star to do. Elvis didn’t need to stand beside Frank to reclaim his audience; he might even, working alongside a performer old enough to be his daddy, look a bit dated; and if Frank was really that big, Elvis should have been chary of sharing his brilliant return with him: He was a rival.

  From Frank’s point of view, it was even stranger. He had to pay for it through the nose, for one thing: Elvis’s people milked Frank for $100,000 for a mere ten minutes of Presley’s time (“You should make in a year,” said Sammy Cahn, whom Frank asked to produce the special, “what Frank is losing on this show”). Too, Frank hated rock music; Elvis was one of those “sideburned delinquents” he’d railed against a few years earlier, an upstart who’d edged into Frank’s record sales and glory. And the two had no natural rapport, not as singers, not as icons, not even as men. Poor, southern, and white wasn’t one of the guises Frank ever tried on for size, and Elvis actually idolized Dean among older singers of standards.

  But Elvis was in that spring of 1960 the only star who shone with anything like Frank’s intensity, and his return from a two-year absence was a big, big draw. To put the two of them together made a twisted kind of sense: Elvis could accept Frank’s attention as an emblem of his place at the acme of showbiz, and Frank could both augment his hepcat credentials and have a hit, at last, on TV.

  Lord knew he needed one: His three most recent shows, also ABC specials, had all flopped. This would be his last show in his current contract, and, like an athlete about to go free-agent, he wanted to make an impression on potential new employers. So he didn’t care how much he had to fork out or whom he had to pretend to be happy to see to do it; it was show business, yes, but it was business, too.

  The atmosphere around Miami’s mini-Summit shows and the “Welcome Home Elvis” special was as charged as it had been in Vegas two months earlier. The town was crawling with Rat Pack adjuncts like Jack Entratter, Skinny D’Amato, and Texas oilman Bob Neal, a skirt-chaser of such renown that Jack Kennedy once greeted him with “My God, Bob Neal! That’s the man we’d all like to be!” Desi Arnaz was in town, and Nancy Sinatra, and even Sam Giancana, who sported himself by tossing cherry bombs under people’s chairs, a diversion that so amused Frank that he joined right in, even when Peter and Sammy were Giancana’s defenseless victims. (Frank seems to have caught the fireworks bug from Giancana: Mia Farrow later remembered him frequently stuffing his pockets with cherry bombs before hitting the town, apparently intending to avoid the press by creating explosive diversions.)

  Giancana was in town for more than just shenanigans, however. Operation Mongoose, the CIA-Mafia cabal against Castro, was gestating, and he was speaking to a frightening stew of conspirators interested in recovering lost property in Cuba. Moreover, the Chicago Outfit had had some interests in Florida ever since Capone took up vacationing there; he could check up on a few things, call it a working holiday.

  Whenever he hit Miami, Giancana immediately hooked up with Frank’s old buddy Joe Fischetti, a handsome, enigmatic figure known around town as Joe Fish. Fischetti was one of the Fischetti brothers who visited Lucky Luciano in Havana with Frank just after the war; his older siblings, Rocco and Charlie, were capos in Chicago, the city that became theirs after their cousin Al Capone went to jail and lost his marbles. But Joe had neither the muscle nor the brains to pull his weight at home; like Fredo Corleone, he was sent somewhere warm to keep watch of things under the protective eyes of the local mob—the Trafficante family of Tampa in this case. Joe ran a few restaurants, kept tabs on—and pieces of—little Miami vices, and was always ready with a broad or a place to crash or somewhere to stash something—or someone—you didn’t want found. He was Chicago’s guy in Miami and, as such, Frank’s guy there, too. And he was as reputable as, say, Johnny Rosselli; you could let him meet good company and not worry about what he might do. He was, as far as the IRS was concerned, a restaurateur and hotelier who received a regular salary from the Fontainebleau as entertainment director. But his position with the hotel was strictly a no-show affair that amounted to little more than his guaranteeing that the hotel had access to Frank’s services. He got more than a grand a month on the books: pure tribute.

  And since it was Joe Fish’s town, and it was Joe Fish’s hotel, the summiteers got treated right. When somebody at the front desk made the mistake of putting Joey Bishop in a suite on the seventh floor (Frank and the rest were up on fifteen), Frank called downstairs and threatened to walk unless that was changed. Joey, happily ignorant of the fuss, was preparing for the night’s show. “I’m in my room, writing some material,” he remembered. “Six bellboys came running in. They didn’t take out my clothes. They took out the drawer with the hangers and everything. I thought the place was on fire.”

  After three nights of Summit shows, the “Welcome Back Elvis” special was staged. Dean, making more movies than even Frank, skipped town for L.A., but the rest all appeared, even Peter, who was a bit of all right as a song-and-dance stooge for Sammy. (The wan show’s highlight turned out to be their “Shall We Dance?” number from the Sands, with Frank and Joe butting comically in and giving the hour its only touch of Summit spontaneity.)

  The hour was built inanely around the conceit that Frank was “giving Elvis back” the two years he’d lost to the service by introducing him to songs and showbiz events he’d ostensibly missed. While the structure did afford Sammy and Frank the chance to sing some recent hits, the show was continually dragged down by dull production numbers, inane emcee patter read by Frank and Joey with a clumsiness that bespoke indifference rather than breeziness, and a bizarre and depressing routine featuring Nancy Sinatra as part of a human time machine—three young dopes who marched in a kind of lockstep and handed out pieces of paper describing the next historical moment to be presented.

  Elvis made a brief appearance at the beginning, sauntering out in his army threads to a shrill, frenzied greeting from the live audience; he ended the opening number by singing a chorus, with special lyrics, of “It’s Nice to Go Traveling,” the brilliant final cut from Frank’s Come Fly with Me LP. As a finale, he came back, this time in a tuxedo (complete with western bow tie), to trade numbers with his host: Elvis sang “Witchcraft,” Frank did “Love Me Tender.” Frank won the singing hands down, but it was Elvis’s night.

  What the hell: When the show aired two months later, the ratings were the best ever for a Sinatra show; he wouldn’t croak from a little magnanimity.

  If the “Welcome Home Elvis” show enabled Sammy to catch up with his old buddy Elvis—the two had once been early casting choices to play opposite one another in The Defiant Ones—it also forced him to deal with one of his bêtes noires: the virulent racism of Miami, a city that, like Las Vegas, beckoned him with lucrative and prestigious work opportunities, then treated him with disdain as just another black face.

  By 1960, Sammy had himself risen high eno
ugh in the world—and was standing close enough to Frank—not to have to stay in the black ghetto across the Intercoastal Waterway from the fabulous hotels of the Miami Beach strip; like everyone else on the show, he was welcome to stay at the Fontainebleau and had similar privileges next door at the Eden Roc. But the rest of the city was a dicier prospect; as in Vegas, he tended to entertain himself indoors a lot.

  More and more, Sammy was beginning to resent the whole thing—the slurs and ad hoc integration and limitations. And he was beginning, for the first time in his life, to see the struggle less as a matter of Sammy’s being accepted than as one of an entire race’s being shown a table in the nightclub of life.

  Ever since he’d left the army, he felt racism with painful depth. Treated as a subhuman since boyhood because of the color of his skin, he’d grown to loathe his own flesh; he would occasionally squeeze his hands together just to see what it looked like to be, briefly, white. It wasn’t an uncommon feeling, he knew: “I really have at least subconsciously wished, like probably every other Negro, that there was some way I just wouldn’t have to go through all of it.”

  He had always been in favor of integration, naturally, but by his own admission it had been only his own acceptance into the wider, whiter world that interested him. “I didn’t give a damn about no race cause,” he said. “I knew about the problems, but I just didn’t care. I didn’t care about nobody but me.” He was a curious sort of pioneer, breaking down barriers that almost no other black man would ever encounter—“Long before there was a civil rights movement I was marching through the lobby of the Waldorf-Astoria, of the Sands, the Fontainebleau, to a table at the Copa. And I’d marched alone. Worse. Often to black derision”—but doing so for selfish, even ignoble reasons.