Sinatra

by James Kaplan

  Bizarrely, Giancana continued to laugh each time he took the Fifth while Kennedy asked him about several specific accusations. Exasperated, the committee counsel finally asked, “Would you tell us anything about any of your operations or will you just giggle every time I ask you a question?”

  “I decline to answer because I honestly believe my answer might tend to incriminate me,” Giancana replied.

  “I thought only little girls giggled, Mr. Giancana,” Kennedy said.

  It was tough talk from the boyish, high-voiced committee counsel, all of thirty-three years old on that June day—and exceedingly strange talk too, given that both his father and his adored older brother shared at least one close connection to the man on the stand: a friendship with Frank Sinatra. Further connections were soon to come, and Frank would help facilitate them.

  —

  A certain part of him fell away when he wasn’t making records. How to fill the void? That June and July, he commuted to the MGM back lot and played soldier from 11:00 a.m. to 6:00 p.m. each day, shooting Never So Few amid fake foliage simulating the steamy jungles of Burma. Boredom was the real enemy. To divert himself one day, Sinatra had the entire roster of the Milwaukee Braves, including the greats Hank Aaron and Warren Spahn, to lunch in the Metro commissary. During another lunch break, he brought Nelson Riddle and a full orchestra onto a soundstage to rehearse for a Capitol recording session. The actor Dean Jones recalled conspiring with Steve McQueen to rig Sinatra’s trailer with cherry bombs. A highlight of the production, Jones remembered, was when Frank’s toupee fell off during a fight scene. Utterly unfazed—he was after all the star, co-producer, and master of all he surveyed—he retired to his makeup chair to have the wig glued back on.

  He was beginning to see himself as a key part of the Kennedy team. One night in late June, he threw a dinner party on Bowmont Drive for Governor Abraham Ribicoff of Connecticut, the man who had nominated Jack Kennedy for the vice presidency at the 1956 Democratic National Convention and one of the first public officials to support JFK’s presidential run. Dean Martin and Shirley MacLaine were present, as were Tony Curtis and Janet Leigh and nineteen-year-old Nancy Sinatra, sans Tommy Sands, the young singer-actor she’d lately been dating.

  Frank’s own love life—as opposed to his sex life—was sparse. Lady Beatty, after dallying awhile with him in the States, returned to Europe, where she took up with Aly Khan, then married Stanley Donen. Frank was not heartbroken. Despite troublemaking news reports, mostly from Europe and entirely invented, he did not have an affair with his Never So Few co-star Gina Lollobrigida, who had been accompanied to Hollywood by her manager-husband. (Despite MGM’s marketing strategy—the trailer for the film showed Frank and Gina kissing strenuously under titles reading, “SOONER OR LATER THIS HAD TO HAPPEN—SINATRA MEETS LOLLOBRIGIDA,” as the screen burst into process-shot flames—the lack of on-screen heat between them was palpable.)

  It was time for some therapy by geography.

  When his work on the picture was done in early July, Frank and Dean flew to Miami to attend the wedding of Sam Giancana’s nineteen-year-old younger daughter, Bonnie. “Giancana apparently chose Miami Beach for the wedding to avoid the publicity he received when his 24-year-old daughter [Antoinette] was married to a bartender in Chicago,” UPI reported. Press coverage of the earlier affair, which had cost $20,000 and featured two bands, a four-foot wedding cake, eight hundred guests, and Joey Bishop as the main entertainment, “apparently resulted in embarrassment to Giancana when mobster names on the guest list were published widely,” the account continued.

  Determined not to be embarrassed again, Giancana did all he could to keep the press at bay. The wire-service reporter on the scene could only pick up tidbits:

  Giancana, who appeared last month before the Senate Rackets Committee investigating the prostitution and pinball rackets in Chicago, dabbed at his eyes with a handkerchief when he gave his daughter away.

  But little else could be learned about the affair. Guests slipped unobtrusively into town, attended the ceremony at St. Patrick’s Roman Catholic Church and the reception at the luxurious Fontainebleau Hotel, then left as quietly.

  The hotel even denied that the reception took place. “There is no wedding reception or party of any kind today,” a Fontainebleau spokesman insisted.

  But observers noted burly men guarding the doors to the plush party rooms where bejeweled women and men in dark suits and dark glasses mingled while strolling musicians serenaded them.

  —

  From Miami, Frank headed to New York to see some shows and to be given a personal tour of the UN by the Nobel laureate Dr. Ralph Bunche himself, as the ever-anodyne Louella Parsons reported. But Bunche wasn’t the only distinguished person of multiracial background Sinatra saw while in the city: according to George Jacobs, Frank spent a good deal of time and energy trying to succor the forty-four-year-old Billie Holiday in her final illness.

  Holiday, just eight months older than Sinatra, had been a success long before he was, recording through the mid- and late 1930s with Benny Goodman, Duke Ellington, Teddy Wilson, Count Basie, and Artie Shaw while Frank, still wet behind those protruding ears, was scrounging for singing gigs in Hoboken. As a very young man, he had gone frequently to hear her perform at small West Fifty-second Street clubs like the Onyx, and he’d been in love with the ragged texture of her voice and her incomparable laid-back phrasing, and in love, too, with Billie herself: her sultry, wounded, distant presence, both regal and ravaged. He learned from her, as from no other singer, the intertwined arts of phrasing and storytelling. As Frank told Ebony magazine in 1958, “With few exceptions, every major pop singer in the U.S. during her generation has been touched in some way by her genius. It is Billie Holiday who was, and still remains, the greatest single musical influence on me. Lady Day is unquestionably the most important influence on American popular singing in the last twenty years.”

  In July 1959, Holiday, a longtime narcotics addict, lay dying of cirrhosis of the liver and multiple organ failure in Harlem’s Metropolitan Hospital. She was also in heroin withdrawal. She was not only mortally ill but also under arrest; the police had recently found a glassine envelope of the drug in her purse. Picketers with signs reading “Let Lady Live” marched outside the hospital. William Dufty, who was Holiday’s close friend as well as the author of her autobiography, Lady Sings the Blues (Holiday bragged that she had never read it), told the singer’s biographer Donald Clarke, “This was a horrifying outrage, arresting somebody in their hospital bed. But how to impress it on people’s consciousness?” Dufty began putting together a petition to be sent to the office of Mayor Robert Wagner of New York. He recalled,

  There was the problem then between Mayor Wagner and the police as to whether [addicts] should be thrown in jail or treated in hospitals. Dorothy Ross [a press agent] and I were calling people like Frank Sinatra, Steve Allen, Basie, Ellington, Ella, Sidney Poitier. And nobody responded. Sinatra said, “Wagner hates my ass.”

  Jacobs tells a somewhat different story. According to the valet’s vivid account, he and Frank visited a gaunt and wasted Lady Day in her hospital room, where three cops were stationed at the door. “A beautician was doing her hair and nails, and she was smoking outside her oxygen tent and begging the nurse to get her a beer,” Jacobs recalled. She was thrilled to see Sinatra, who made happy talk about how he’d loved her latest album and how much she’d influenced his phrasing when he was starting out with Harry James. “I may have showed you how to bend a note, Frankie, that’s all,” Holiday said. Then she leaned over to him and whispered, so the police couldn’t hear, “Will you cut the shit, baby, and get me some dope?”

  Apparently, Sinatra, despite his hate of drugs, tried to get heroin for Holiday through legitimate channels, as a medical necessity. When that didn’t work, Frank bought it himself from a dealer. But with the police outside Holiday’s door, there was no way to get the drugs through. The singer’s liver failed, and she went into a coma.
She died on July 17.

  Sinatra was disconsolate, and guilty. He holed up in his apartment, drinking, weeping, and playing her records over and over. Then, four days later, he brushed himself off and headed for Atlantic City.

  —

  Frank Sinatra first met Skinny D’Amato in the summer of 1939, when the boy singer performed with Harry James and his orchestra at the Steel Pier, a thousand-foot-long pleasure palace jutting out from the Boardwalk over the Atlantic surf. Skinny—Paul was his given name—was running a small gambling joint on Pacific Avenue at the time, but his importance in that wide-open city by the sea was large. He was a fixer, a genial man-about-town who knew every somebody that passed through and knew exactly what kind of fun they liked, too. Harry James was a pal, and James’s new singer would soon become one, too.

  Frank and Skinny hit it off from the start. Both were Italian Jersey boys, both disdained the police and other authority figures (Skinny had recently served time for pimping), both loved nightclubs, and the night. Seven years older than Sinatra, almost to the day, D’Amato was good-looking in a street kind of way—long face, prominent nose, spit curl—and possessed a kind of hood-elegant flash. He wore beautiful suits, French cuffs, silk ties, and custom shoes—all this at a time when Frank was not only poor but still fresh out of Hoboken.

  Skinny also palled around with the important types who came from Philadelphia to play, men like Marco Reginelli, the reputed head of the Mob in the City of Brotherly Love. Rumors persist to this day that D’Amato himself was mobbed up, or at the very least in business with organized crime—some say he was fronting for Reginelli—but the truth seems to be that while he liked and respected these men, he had been in jail once and didn’t want to go back. He worked hard at keeping his dealings legitimate, and mostly managed. The young Frank Sinatra watched and admired Skinny’s easy style and his way with these uomini di rispetto. Tommy Dorsey, for whom Sinatra would leave Harry James that fall, might have been Frank’s most important early mentor, but Skinny came first.

  In 1943, D’Amato and a rough-edged partner named Irvin Wolf bought the 500 Café, a yellow-brick-fronted building with a theater-style marquee on South Missouri Avenue, just a couple of blocks up from the Boardwalk. The Five, as everyone called it, was a nightclub with an off-the-books gambling casino in the back room, and under Skinny and Wolfie’s guidance it became an Atlantic City institution. In 1946, for various legal reasons, its name was changed to the 500 Club.

  In July of that same year, D’Amato and Wolf were about to fire a struggling twenty-year-old nightclub comic named Jerry Lewis—his act consisted of making faces while he lip-synched to Enrico Caruso and Carmen Miranda records—when Lewis came up with a desperate save: he told the club’s owners he could do a double with a handsome nightclub singer he’d met when they were both working at the Glass Hat in New York. The singer was Dean Martin.

  Skinny and Skinnier, circa late 1950s. In Paul “Skinny” D’Amato, who ran the legendary 500 Club in Atlantic City, Sinatra found some of the same traits that drew him to Dean Martin—an easy style and a certain way with the uomini di rispetto. (Credit 12.1)

  Martin and Lewis exploded out of Atlantic City to national fame and quickly discovered that unlike the Five, most major nightclubs were owned behind the scenes by the Mob. This was certainly true of New York’s Copacabana, where Frank Costello called the shots and where, on April 8, 1948, they opened for the first time. Skinny D’Amato brought Frank Sinatra to the Copa that night to show off his good pal and his sensational discoveries to each other; it was the first time Frank met Dean and Jerry. “Frank’s career was just beginning to take a nosedive, and he had performed for the first time at the 500 Club the summer before,” writes D’Amato’s biographer Jonathan Van Meter. “His acquaintance with Skinny had turned a corner into something more intimate.”

  —

  Sinatra’s career might have been slumping, but Atlantic City, which had a large Italian-American population, loved him, and he loved A.C. The ocean air revivified him, reminding him of past glories. After the bad spring and summer of 1951—in May, Frank, under the aegis of Columbia’s Mitch Miller, recorded “Mama Will Bark”; in August, after an especially nasty quarrel with Ava at Lake Tahoe, he had made a halfhearted suicide attempt, taking just enough sleeping pills to make himself sick and get her attention—Skinny D’Amato gave Sinatra a huge shot in the arm, booking him over Labor Day at the 500 Club, now one of the hottest joints in the country, and paying him at his top rate. “When Frank got to town, Skinny took him around to all his favorite joints, showed him off, and boosted his ego,” Van Meter writes. “A couple of days before his first performance at the 500, Skinny went to a local jewelry store and bought Frank a gold watch. When he gave it to him, he said, ‘Don’t ever think you’re down-and-out, pal. This is to remind you that when you come back you’re going to be bigger than ever.’ ”

  Once again, he was a smash hit. Every show—even the 4:00 a.m.—was mobbed.

  And, while Frank was playing the Five, Skinny put in a call to Moe Dalitz—the Cleveland Mob boss who in 1950 had taken over the building and ownership of the Desert Inn when the front man Wilbur Clark ran out of money—and persuaded him to book Sinatra for five weeks at Las Vegas’s newest and most luxurious hotel-casino. The DI was Frank’s first Vegas stand and, as a bonus, the place where he first met Bill Miller, who was to become his nearly lifelong pianist and musical secretary.

  Once his comeback was solidified, Sinatra’s loyalty to Skinny and the 500 Club was absolute. In the summer of 1956, when Frank was unhappily shooting The Pride and the Passion in Spain, he thought longingly of Atlantic City, sending D’Amato a telegram that simply read, “How about August 24, 25, 26, 27?” He signed the wire “El Dago.” That summer, and for years thereafter, Skinny announced Sinatra’s presence with a billboard that read, simply, “He’s Here!” Once the stand was over, the message changed to “He Was Here!”

  In 1959, when Frank had become the biggest thing in show business, he told Skinny he would do his nine nights gratis. The result was a nine-day mob scene. Sinatra, who returned as a conquering hero, flying in Red Norvo’s quintet, Bill Miller, and a dozen Hollywood friends on a chartered plane, had to travel the streets of Atlantic City by police car. “Skinny often said, ‘Many entertainers can fill up a room, but Frank filled up the town,’ ” writes Sinatra archivist Richard Apt. One night, the crowd on Missouri Avenue grew so frenzied that a police cruiser—accounts fail to mention whether or not it was the one Frank was riding in—was almost turned over.

  The crowds jamming the club, sometimes for six shows a night, were no less passionate. Apt recalled being taken by his parents to the 500 that July to celebrate his tenth birthday. “The smoke bothered my eyes,” he writes.

  Ventilation was a rumor in 1959. I consistently dipped my cloth napkin into my water glass, dabbing my eyes over and over. More than six hundred people were packed into the little saloon. Next to us were two nightclub owners from Boston. I remember them saying that it was their sixth night in a row and that they were getting tired of eating bad steak…

  Then Red Norvo said, “…now our boy singer,” and out from the wings came Frank Sinatra. Somewhere in between “High Hopes” and “All the Way” he noticed me and leaned over to our ringside seats and gave me a couple of exaggerated winks. My mother later told me that I blushed quite deeply.

  He had this effect on people. At one performance, Earl Wilson reported, Frank stamped out a cigarette butt onstage. “ ‘Kick that cigarette butt over to me and I’ll give you $20,’ a woman fan of supposedly mature years called over to the bandleader—who complied. She took it away as a souvenir.”

  In his dressing room backstage, Sinatra, like a lord of the manor, wore a smoking jacket with an emblem depicting a bottle of Jack Daniel’s on the breast pocket and the initials JD embroidered underneath. And in his hotel, the Claridge, where he and his entourage were occupying the entire first floor—Frank’s fear of heights ge
tting the better of him and anyone who wanted an ocean view—he threw a notable, and notably protracted, party, during which, according to FBI files, Hollywood mixed with organized crime. In 1960, an agent filed a report, titled “Samuel M. Giancana,” in which an informant “advised on September 16, 1959, that [Giancana] had recently been to the Claridge Hotel in Atlantic City, New Jersey, in order to see Frank Sinatra…The informant stated when they [sic] got off the elevator on the first floor they were approached by two ‘tough looking men’ and asked for identification and the purpose of their visit. The informant stated one individual in Sinatra’s suite at this hotel was identified to him as Joseph Fischetti, described as the ‘well known hoodlum from Miami.’ ”

  In another report, from 1962, an FBI agent had interviewed a showgirl whose name was redacted from the file. “She stated that at the age of approximately eighteen she became employed as a professional dancer, appearing in chorus lines at various hotels, night clubs and casinos around the country,” the report read.

  She became acquainted with Frank Sinatra during approximately 1958. During this period she traveled throughout the country and worked for some time at the Tropicana and Riviera Hotels in Las Vegas.

  In July 1959, she attended a party given by Frank Sinatra in Atlantic City, New Jersey, at the Claridge Hotel. Sinatra at that time was appearing at the 500 Club as the featured entertainer. The party referred to lasted approximately two weeks and normally started at about 8:00 P.M. and lasted until about 4:00 or 5:00 A.M. the following morning…She mentioned other persons in attendance at this affair, in addition to the ones mentioned above, as actress Natalie Wood, actor Robert Wagner, then the husband of Natalie Wood, Rocco Fischetti, his brother, Joseph Fischetti, John Foreman (true name John Formosa) and Paul “Skinny” D’Amato.