Sinatra

by James Kaplan

  There was an intense—and complex—chemistry between the two. Pat Lawford, according to Jacobs, “had had an admitted crush on Frank since his crooner days”; as for Frank, the former valet writes, “Mr. S smelled a potential seduction of one of the most high-profile ‘super-broads’ in America…The prospect of Pat Kennedy opened Mr. S’s eyes to the even more exciting prospect of John Kennedy.”

  Thanks to an organized and energetic presidential campaign begun virtually the moment he lost the 1956 vice presidential nomination, Jack Kennedy’s presidential prospects had been growing steadily more exciting through the late 1950s. In a field of gray-colored candidates—fiftyish politicians like Adlai Stevenson, Stuart Symington, Lyndon Johnson, and Robert Meyner—the impossibly glamorous senator from Massachusetts—a Harvard graduate, a reputed war hero, and a Pulitzer Prize winner for Profiles in Courage, the book about breakaway senators that bore his name on the cover—stood out like a bird of paradise.

  Nevertheless, a look beyond Kennedy’s sexy exterior into his political heart might have given Sinatra pause. Frank had grown up imbued with FDR liberalism; Jack Kennedy had not. As a junior senator in 1954, he had dragged his feet on censuring Joseph McCarthy (for whose Red-baiting Senate Permanent Subcommittee on Investigations his brother Bobby had worked as an assistant counsel and whom Pat Kennedy had briefly dated). He’d waffled on the Civil Rights Act of 1957. “I wish Mr. Kennedy had a little less profile and a little more courage,” Eleanor Roosevelt famously remarked. Amid 1950s paranoia about Communism, John F. Kennedy and his whole family were eager to distance themselves from Stevenson, whom most of America considered pinkish and an egghead to boot (the candidate’s bald dome and refined manner had originally inspired the term), and the Democratic Party’s liberal wing.

  Yet class and charisma, whatever the substance beneath, held a deep and unsalubrious attraction for Sinatra—witness Lady Beatty—and Jack Kennedy possessed both in spades. “For Sinatra,” Ronald Brownstein writes,

  Kennedy seemed to represent more than just power; despite his own rakish behavior, JFK conveyed a weight and solidity suggestive of Harvard, summers on the Cape, lazy days surrounded and protected by a vivacious family. All that the bright, garish Rat Pack lifestyle—a blue-collar fantasy of what it meant to be rich—eminently lacked. Like his acceptance at the [Bill and Edie] Goetz table, Kennedy’s favor gave Sinatra respectability—a reason to be admired, not just feared, by his peers.

  And Kennedy, a longtime habitué of Hollywood who moved easily among movie stars, feeling himself their equal, if not their superior, was an ahead-of-his-time politician, one who understood the enormous political potential of show business and its players. He was also enthralled by the business and its players themselves, and no one was a bigger player than Frank Sinatra. As the two men rose to the peaks of power, they were destined to enter each other’s orbit.

  Joseph P. Kennedy, both explicitly and by example, had taught his son well. He had understood the financial possibilities of the movie business when he bought into RKO Studios in the 1920s; he had formed a longtime liaison with Gloria Swanson not just because of the charms of her person but because of her worldly power as a film star. He had consciously cultivated Sinatra at Cal-Neva for much the same reason, but for other reasons as well.

  Joe Kennedy’s chief aim in life, his reason for being, was to get his oldest living son elected president of the United States. After two decades of successful investment banking, he had the money to do it, and beginning with Jack Kennedy’s congressional campaign in 1946, he’d set about converting money into power. “We’re going to sell Jack like soap flakes,” he famously said, and he was as good as his word, laying out enormous amounts for billboard space, newspaper ads, and radio spots.

  Once the presidential campaign began, the elder Kennedy raised his game, spending ever more lavishly. The stakes were immeasurably higher, and so were the goals: magazine covers now instead of billboards. And men of national influence, not just local political bosses, had to be rallied to the cause. Some of these men occupied high positions in organized crime.

  In his life of Joseph Kennedy, David Nasaw devotes just a single page to debunking the longtime allegations that Kennedy was involved in bootlegging during Prohibition, mentioning “unsubstantiated, usually off-the-cuff remarks [on the subject] made in the 1970s and 1980s by Meyer Lansky, Frank Costello, Joe Bonanno, and other Mob figures not particularly known for their truth telling.” The implication is to dismiss any other connection Kennedy might have had, at any time, with any of these men.

  Sheer practicality, Nasaw argues, kept Kennedy from having anything to do with the Mob. “He had disposed of his liquor import business and his stake in Hialeah because he did not want his children to be tarnished with the stereotypes he had so scrupulously avoided all his life,” the biographer writes.

  He had lived his life and made and kept his millions by carefully evaluating risk/reward ratios and avoiding any and all unnecessary dangers, in business and politics. It would have been extraordinarily reckless—and he was not a reckless man—for him to do business with or consort with known mobsters, especially as they had nothing to offer him he could not obtain elsewhere.

  The last sentence contains two ideas: The first, that it would have been supremely reckless for Joseph Kennedy to consort with mobsters, is clearly true. The second, the notion that the Mob had nothing to offer him, is problematic, to say the least. And the one sure way to deal with the problem of needing something without being able to ask for it directly is to proceed through intermediaries.

  The Mob boss Joe Bonanno’s son Bill Bonanno, whom Gay Talese considered trustworthy enough to collaborate with on Talese’s massive history of the Bonannos and the Mob, Honor Thy Father, asserts that this is precisely what Joe Kennedy did. Kennedy wanted organized crime’s help in rallying organized labor behind his son, and so in the winter of 1959, according to the younger Bonanno, he sent a representative to talk with a representative of Joe Bonanno’s.

  “I was instructed to go back…to New York and sound out other leaders about a concerted effort to back JFK,” Bill Bonanno told Anthony Summers. “The divisions over Kennedy were deep. Joe Profaci [a New York Mob boss], for example, said he just didn’t trust Kennedy. Midwestern leaders—in Cleveland and Michigan—had let it be known that we should get behind someone who was more rooted in the unions, where we had more influence.”

  “Giancana, on the other hand, appeared to be in favor,” Summers writes, “and Joe Kennedy needed a way to reach out to him.”

  That Frank Sinatra and Sam Giancana were friends was a fact of which Joe Kennedy would have been well aware. And Giancana, feeling the heat of the Senate committee on which Kennedy’s younger son served as counsel, needed something from the Ambassador, too.

  —

  The Joe Kennedy whom George Jacobs remembers was a very different person from the rough-edged but dignified power broker portrayed in David Nasaw’s biography. A late-1950s weekend Kennedy spent at Sinatra’s desert home made an indelible impression on Frank’s valet, who at first assumed, not unreasonably, that the cold-faced Ambassador was another of Mr. S.’s gangster pals. For one thing, there was the resplendent welcome Sinatra laid on, including a quintet of hookers flown down from Vegas; for another, there was the guest of honor’s dinnertime patter, a steady barrage of nasty cracks about blacks and Jews. Especially Jews. To the onetime studio owner, the former furriers and glove makers who had founded Hollywood were “Sheenie rag traders”; Kennedy called Louis B. Mayer a “kike junkman.” Frank sat through it all with a forced smile.

  Why? Because Joe Kennedy held the key to something that Frank wanted badly: political power. Sinatra’s Democratic politics went back to Dolly’s Hoboken and the early FDR days. But under the old, Waspocratic worldview, still tenacious in America through the 1950s, an Italian-American like Frank, no matter how much money he made from music and movies, was still just a minstrel. He could sit at the feet of power, he coul
d contribute to the cause, but the grown-ups, the white men who went to Protestant churches, made the decisions. Now it looked as though there could be a real sea change—a young, Catholic, ethnic president—and Sinatra wanted in. And “in” meant access and influence: quantities that Joe Kennedy carried in his attaché case.

  —

  The royal road to the son passed through the father. “I think that in understanding Jack Kennedy, you have to go back to his father and [Jack’s] growing up, and how his mother was treated as this side issue over here—the saintly mother, but not the person you really had any fun with,” said Alan Livingston’s widow, Nancy Olson Livingston, who knew JFK from the late 1940s on. Jack Kennedy, the soap flakes the old man was selling, appears to have paid his first visit to Frank’s Palm Springs place in the eventful summer of 1958. But while JFK might have been a chip off the old block in some respects—his cool toughness, his sexual voracity—he lacked the old man’s blunt force, his unapologetic gracelessness. Those were survival skills for Joe Kennedy, who’d had to fight his way into polite society, had had to slug it out with robber barons and just plain robbers. Jack had only had to fight Japs in the South Pacific. He was brave, but he was spoiled, an Irish-American prince supremely confident of his charm and good looks. (Nobody had ever accused Joe Kennedy of being handsome.) And his charm, which comprised a keen intelligence and a quick wit, was overwhelming. Frank fell for him—much as he had fallen for Dean—like a ton of bricks.

  Few people, male or female, had the power to resist Jack Kennedy. George Jacobs was no exception, although the photo-realistic portrait he gives of the president-to-be is remarkable in its coarseness. Jacobs saw JFK with his hair (and sometimes his pants) down, and his picture of the man is very different from the iconic images of the young president with his thumbs hooked in the pockets of his suit jacket or reclining in sweater and sunglasses on his yacht the Honey Fitz. Like his father (and like Frank), Jack Kennedy lacked apology. He knew what he wanted, and he said so. But unlike the old man, he said so with a twinkle.

  “As much as I disliked his father, that’s how much I was crazy about John Fitzgerald Kennedy,” Jacobs writes.

  He was handsome and funny and naughty and as irreverent as Dean Martin. “What do colored people want, George?” he asked me the first time he visited Palm Springs, not long after Mr. S and Peter Lawford became bosom buddies.

  “I don’t know, Mr. Senator.”

  “Jack, George. Jack.”

  “What do you want? Jack?” I asked.

  “I want to fuck every woman in Hollywood,” he said with a big leering grin.

  And that, in short, was why he was there. Kennedy’s close friend and campaign aide, Dave Powers, tried to soften the focus. “His fondness for Frank was simply based on the fact that Sinatra told him a lot of inside gossip about celebrities and their romances in Hollywood,” Powers told Kitty Kelley in 1982. George Jacobs certainly confirms JFK’s love of celebrity dirt, which Kennedy loved to dig for while Jacobs, an expert masseur, kneaded his bad back. “I would work on his back for a good hour, all the while being peppered with prurient questions about his favorite topic, celebrity ‘poon-tang,’ as he liked to call it,” the valet recalled. Whenever Jacobs tried to ask a political question, the senator firmly steered the conversation back to whether Janet Leigh was cheating on Tony Curtis or what was going on with Eddie Fisher and Debbie Reynolds. Kennedy apparently read every issue of Confidential magazine.

  Sex, Jack Kennedy’s obsession, was always the main topic. But he didn’t want to just talk about it. He knew that no one in Hollywood—meaning no one in the world—had more sex than Frank Sinatra: it made Frank a hero in Kennedy’s eyes, and, more important, it promised Kennedy the kind of access he was most interested in.

  Each man knew what the other could do for him; each wooed the other in his own way. Frank came to Jack with an agenda, but also with a large degree of idealism and genuine affection. Jack came to Frank with a cool eye for what he could get—not just sex, but the political power of Hollywood—and the charm to convince Sinatra the affection he showed was real. By October 1958, Sinatra, who had told the press, “Senator Kennedy is a friend of mine,” had endorsed JFK for the presidency. In November of that year, Walter Winchell speculated in his column that John F. Kennedy, if elected, might appoint Frank Sinatra ambassador to Italy.

  —

  One night in May 1959, Frank and Dean were the emcees at the SHARE Boomtown show, a star-studded charity event at the Hollywood Moulin Rouge. It was a wet and wild evening, all partygoers clad in outlandish western regalia and imbibing liberally. Dean made his entrance from the ceiling on a wire-suspended saddle slowly lowered sixty feet to the stage. When the saddle was hauled back up, Dean called, “So long, Jerry.”

  “Because it was an ‘inside’ soiree, the boys were really swinging,” UPI’s Hollywood correspondent Vernon Scott wrote. “The singers rarely were without a highball in their mitts…The longer the show went on the wilder it became. As leaders of Hollywood’s ‘clan,’ Martin and Sinatra had the jam-packed Moulin Rouge crowd howling with glee.”

  A funny thing happened when Sammy Davis Jr. came on to perform “Birth of the Blues.” While Frank and Dean ad-libbed a boozy introduction, Frank looked at Sammy and Sammy looked at Frank. Suddenly, with the all but undetectable nod of a true padrone, Frank was beckoning Sammy over, and before anyone knew what was happening, the two were embracing, to the crowd’s loud delight. The feud was done.

  After Frank and Dean had vocalized separately, they sang a pair of duets, “Come Fly with Me” and “I Can’t Give You Anything but Love, Baby.” As the applause for the second number died down, Sinatra and Martin went into a shambling Sammy Cahn parody, to the tune of “You Oughta Be in Pictures”:

  We’re glad that we’re Italian,

  Authentic Abruzzi,…

  Dean owned “that lodge called Dino’s,” he crooned; for his part, Frank put in that he had “a hunk of Puccini.”

  The well-oiled showbiz crowd ate up the inside humor: though Sinatra had wined and dined for years at Patsy D’Amore’s Villa Capri, he’d recently opened his own Italian restaurant, Puccini (named after his favorite composer), on South Beverly Drive in Beverly Hills. His partners in the venture were Hank Sanicola, Mickey Rudin, and Peter Lawford, though apparently Lawford, a notorious tightwad, didn’t put up a dime. He didn’t have to: he was married to a Kennedy. And by May 1959, Patricia Kennedy Lawford’s brother had become the presumptive Democratic candidate for the presidency.

  12

  Oh, you’re a colorful gypsy.

  —BING CROSBY TO FRANK, ON THE FRANK SINATRA TIMEX SHOW, OCTOBER 1959

  At the Desert Inn in March 1959, a process server walked up to a short, dapper, bespectacled man, spoke his name—his real name, not Sam Flood, the handle under which he’d checked into the DI—and handed him a subpoena. The surprised recipient was Frank Sinatra’s friend Sam Giancana, making hay in Vegas during the slim interval between Fidel Castro’s New Year’s Day shutdown of Havana’s casinos and the Nevada Gaming Commission’s 1960 issuance of its first so-called Black Book, a list of “persons of notorious or unsavory reputation” who were to be banned for life from owning, managing, or even entering any of the state’s gambling establishments. Giancana would be one of the eleven charter members of this exclusive fraternity.

  The subpoena ordered the mobster to appear before John McClellan’s Senate Rackets Committee, which had been hunting for him for over a year while he gadded around the country under various aliases, enjoying himself—on the Some Came Running location, among other places—but never failing to glance over his shoulder for whichever white or black hat might be in pursuit.

  Giancana almost seemed to savor the subpoena. He certainly took full advantage of the drama of testifying before a U.S. Senate committee, perhaps considering his appearance a kind of redemption for missing out on the Kefauver Committee when he had been too small a fish to reel in. Now, however, Giancana
was regarded as “either the number one or two man in the shifting hierarchy of the old Capone mob,” and he arrived in Washington on June 9 fully prepared for his close-up. “A handsome-type hoodlum in dark glasses,” UPI reported,

  he came equipped with a printed Fifth Amendment plea which began: “I respectfully decline…” but the word “respectfully” had been crossed out and Giancana never used it. Giancana gave a raucous laugh when committee investigator Pierre Salinger identified him as a top figure in the Chicago underworld. He continued to laugh derisively when asked about a couple of Chicago gangland murders and about his role in a juke box racket.

  Giancana also found amusing a Chicago newspaper interview in which he was quoted as telling his draft board that “he steals for a living.” Committee counsel Robert F. Kennedy brought out that Giancana was rejected for military service because of a “constitutional psychopathic” condition and “strong anti-social trends.”

  “Are you happy at being a thief?” asked Chairman John L. McClellan (D-Ark.). “Is that what you’re laughing about?”