Sinatra

by James Kaplan

  Frank dragged Ava back to their table and pushed her into a chair. When she stood up, he pushed her back down. Giancana watched as if he were at a prizefight, goading Frank on. Then Ava grabbed Mooney’s drink, threw it in Frank’s face, and stalked out without looking back.

  “Buddy boy,” Momo said, “I ain’t never seen anything like that. That was classic.”

  She had humiliated him often before, and they made up again. But the next day, as Frank, Jilly, and others were sitting and talking in Sinatra’s penthouse, the doorbell rang. “Suddenly,” a witness recalled, “Ava walked out of another room all dressed, carrying a suitcase, and headed straight for the door. She opened it, turned, and gave a little wave…Then she walked out. None of us knew what to do. We were so embarrassed for Frank. We were flabbergasted. Frank was stunned. Jilly told me later that the guy at the door was a Spanish airline pilot.”

  It was the close of another chapter, but by no means the last.

  —

  Frank went back to California to play cowboys; Mooney returned to Chicago to take on the Feds.

  In June 1963, Bobby Kennedy, keenly aware of his brother’s potentially explosive connection to Sam Giancana via Judy Campbell, ordered the Federal Bureau of Investigation to put its already tight surveillance of the gangster into overdrive. One side effect of this was that Frank Sinatra, who was spending a lot of time with Giancana that year, began making more guest appearances than ever in Momo’s FBI file.

  Agents observed the mobster in New York, where he’d accompanied his lady friend for the McGuire Sisters’ Ed Sullivan Show appearance. His FBI dossier stated “that while GIANCANA will usually remain in the apartment residence of PHYLLIS MCGUIRE while in New York City, he has been known to stay at the Waldorf Astoria and Madison Hotels in that city. [Redacted] advised that GIANCANA dines constantly at the following New York restaurants: La Scala, The 21 Club, El Morocco, and the Chambord.” Curiously, Jilly’s was not mentioned.

  That month, the bureau instituted what it called “lockstep surveillance”: agents posted around Mooney’s house in Chicago, questioning his neighbors and all visitors, playing one hole behind him on the golf course. Giancana’s chief tormentors were Special Agents William Roemer, Marshall Rutland, and Ralph Hill. They drove the gangster to distraction. “Why don’t you fucks investigate the Communists!” he screamed at them. “I’m not going to take this sitting down! I’m going to light a fire under you guys, and don’t forget that!”

  The oppressive scrutiny led to a highly unusual turn of events, described drily in a July 9 memo from J. Edgar Hoover to Robert Kennedy:

  We have learned through our surveillance of Giancana that he has resumed holding meetings in the Armory Lounge in Forest Park, Illinois. Giancana’s lieutenants have been shuttling carloads of individuals to and from this location where Giancana “holds court” at a large table just inside the entrance.

  Last week one of Giancana’s top lieutenants, Charles “Chuck” English [Charles Carmen Inglesia], contacted our Agents and requested an interview.

  Toward the end of the interview, the memo continued, English, who was slightly intoxicated, tried to persuade Mooney to talk with the agents. Giancana declined, but as the agents got ready to drive away, English came out with a message for Special Agent Roemer: “If Bobby Kennedy wants to talk to Sam, he knows who to go through.”

  “Who?” Roemer asked. “Frank Sinatra?”

  “You said it, I didn’t,” said English.

  The implication was that the attorney general might have something to gain by talking with Giancana—or something to lose if he didn’t. In some cracked gangster way, Mooney felt his role in Operation Mongoose meant that he was legitimately working for the U.S. government, even though he had taken the government’s money and laughed all the way to the bank, contributing nothing to the project except his sinister name. But unknown to Giancana, Bobby Kennedy—officially, anyway—had no idea that he had ever been involved.

  Momo, therefore, felt that the attorney general owed him a debt beyond the one the Kennedys theoretically owed him for their success in the election, while Bobby Kennedy felt that the mobster was merely a nuisance (or worse) to be quashed. But Sam Giancana had another card up his sleeve.

  On the advice of his son-in-law Anthony Tisci, Giancana filed suit against the Justice Department in hopes of winning a court injunction against the FBI for harassment. The grounds: the agency was depriving him of his constitutional right to privacy.

  The papers went nuts. The irony of it! SAD TALE, BUT FBI UNMOVED, read one July 1 headline, noting that the federal district court judge Richard B. Austin had turned down Momo’s petition out of hand, despite an impassioned plea by Giancana’s attorney, the famed civil-rights lawyer George N. Leighton, “that the G-men were ruining Giancana’s social life, making his golf game go to pot and ridiculing him in front of friends and neighbors in suburban Oak Park,” according to UPI’s account. “How would you like it if you were on the 18th hole trying to sink a putt and there were six FBI agents watching you?” Leighton asked the judge, noting that agents had also followed Giancana to church and that Momo had had to hire photographers to take pictures of FBI photographers photographing him. Austin was unimpressed.

  And the judge was unmoved once again when Leighton presented a second petition on the twelfth. But on July 15, Austin agreed to hear Mooney himself. Giancana was taking an enormous risk by taking the stand: he would have to undergo cross-examination by government attorneys who had thousands of pages of documents “detailing every aspect of his criminal history, enough ammunition to put him away for life,” according to a memoir by Momo’s brother Chuck Giancana and his namesake godson.

  But Mooney was enormously confident, telling Chuck he’d win his case for what he called “two very good reasons.” First, he said, his civil rights were indeed being violated, and this he could prove in a court of law. And second, but more important, he’d win because by filing the suit he’d essentially called Bobby Kennedy’s bluff: He was certain the attorney general would back down. As he saw it, Kennedy would have no choice: “I’ll be sittin’ on the stand holdin’ a can of worms. And Bobby’ll be scared to death I’ll open it…because if I do, all their dirty little secrets will come out.”

  Bobby Kennedy blinked. On July 16, UPI reported, Judge Austin changed his tune utterly, ordering the FBI to stop its harassment of Giancana and also placing the FBI’s chief agent in Chicago “in contempt of court for refusing on orders from Washington to answer questions in court.” The orders had come from the attorney general.

  From that moment forward, the court ordered, the FBI had to curtail its “rough shadowing.” Agents tailing Mooney on the golf course would have to let another foursome intervene between them and the gangster. From then on, the bureau could post only one car, rather than a squad, on stakeout at Giancana’s residence. And the FBI car would have to stay at least one block away from the gangster’s house at all times.

  Mooney smiled as the newly sympathetic judge issued his ruling. The next day, as a bureau memo reported, he took advantage of his new invisibility.

  [Redacted] furnished information in [redacted] which reflected that SAM GIANCANA immediately upon cessation of FBI surveillance eluded a surveillance placed by the Cook County Sheriff’s Department and proceeded…to Lake Tahoe, California area where he met with PHYLLIS MCGUIRE, and reportedly stayed at the Cal-Neva Lodge, of which FRANK SINATRA is a part-owner.

  —

  Frank’s next musical project, Reprise Repertory Theatre, seemed a highly worthy one on the face of it. The plan was to heighten brand identity by rerecording four great Broadway musicals (Finian’s Rainbow; Guys and Dolls; Kiss Me, Kate; and South Pacific) with only Reprise artists—a limitation that was also a strength, given the roster Sinatra had to work with: besides himself, there was Dean Martin, Sammy Davis Jr., Jo Stafford, Rosemary Clooney, and Keely Smith; as the pièce de résistance, plans were in the works to sign the Old Groaner himself,
Bing Crosby, to the label.

  Frank also planned, for the first time, to produce the LPs himself. Looked at one way, this self-assignment was nothing new: no matter who was turning the dials in the control booth, Sinatra had always been the true producer of his records. But now he would have to make a number of artistic decisions, including whom to feature and when. He would be a generous impresario. Of the fifty-four numbers cut for the four LPs, Sinatra would sing on only fourteen of them; several of his appearances would be in duets or trios. He started the project with a bang on July 10 by teaming with Dean and Sammy to record Cole Porter’s “We Open in Venice,” from 1948’s Kiss Me, Kate.

  The track is a charming rendition of a sprightly but lesser Porter number: the Summit act now had the comfort and dependability of a well-worn baseball glove, and the trio clicks from start to finish, complete with Vegas-y asides and a dash of Amos ’n’ Andy. Billy May’s slightly cartoonish arrangement (Reprise’s musical director, Morris Stoloff, conducted) moves things along at a brisk—almost manic—rate.

  Yet something is wrong, and though hindsight is inevitable from a distance of fifty years or more, it’s all too easy to ask: Just who was the audience for these albums? Each of the artists involved in the Repertory Theatre had his or her own following and sold (or failed to sell) albums based on airplay, advertising, and TV appearances. But while the concept of a Reprise-branded collection was meant to focus attention on the label, wouldn’t combining artists—as selfless as this might have been on Frank’s part where he was one of the singers—dilute their appeal?

  And there was another important historical factor: by 1963, the golden age of the Broadway musical, which these four uplifting shows of the 1940s and 1950s richly represented, had passed. Broadway would continue to find hits, but the world was changing faster than anybody knew.

  —

  A Repertory Theatre recording session on the eighteenth, with arrangements by Riddle, was more successful. After Frank and Dean did a pleasant enough version of Frank Loesser’s title song from Guys and Dolls, Frank recorded three solo numbers: Loesser’s “I’ve Never Been in Love Before,” from the same show, and Burton Lane and Yip Harburg’s “Old Devil Moon” and “When I’m Not Near the Girl I Love,” from Finian.

  This version of “Moon,” in stereo and with finger snaps, was a worthy successor to the 1956 mono version, also arranged by Nelson. But Frank had never recorded the other two songs before, and both were lovely, imbued with that indefinable something that Sinatra could lend to worthy material from any decade.

  He recorded these beautiful songs on Thursday night; the next day, he headed to Lake Tahoe to meet Sam Giancana.

  —

  Despite the order to back off from Mooney, the Feds managed to keep the heat on, enlisting the aid of other law-enforcement agencies to tail the gangster—“much to the consternation of Giancana, [who] shouted a steady tirade of verbal abuse” whenever he saw he was being followed, according to an FBI memo.

  On July 19, the McGuire Sisters opened in Cal-Neva’s Celebrity Room for a one-week stand. Giancana, who had come to the casino in direct contravention of the Nevada Black Book’s orders, was there to support his lady friend. He and Phyllis stayed in Chalet 50. “Most of the time,” Life magazine subsequently reported, “Sam just stayed put on the front porch of Chalet 50, cultivating his suntan and contemplating the lake. Although he was an unofficial Cal-Neva visitor, he had only to whistle for room service, and a beige station wagon belonging to the lodge was at his beck and call.” Kitty Kelley writes that the FBI photographed Momo and Frank playing golf together that week, even though the bureau’s official position was that it hadn’t followed Giancana to Nevada. (Soon, in any case, a federal court of appeals would reverse the decision, and the FBI would be back on Mooney’s tail.)

  But it wasn’t golf that got Frank in trouble. As an FBI memo put it, tersely,

  [Redacted] advised that during GIANCANA’s stay at the Cal-Neva Lodge, an incident occurred on one evening whereby GIANCANA became involved in a brawl with one VICTOR COLLINS, who was at that time the road manager of the MCGUIRE sisters.

  Collins described the episode to Kelley, in rather more detail. While he was drinking in the chalet with the sisters and Giancana, he said, Phyllis McGuire kept playfully punching him on the arm, a little too hard, every time she passed his chair. Finally, the manager stood up, grabbed McGuire by both arms, and tried to sit her in the chair he had just risen from. Somehow—evidently much alcohol had been consumed by this point—she wound up on the floor, and Giancana became enraged.

  “Sam came charging over from across the room and threw a punch at me wearing a huge big diamond ring that gouged me in the left eyebrow,” Collins recalled.

  I just saw red then and grabbed him, lifted him clean off the floor, and was going to throw him through the plate glass door, but thought, “Why wreck the place?” So I decided to take him outside and break his back on the hard metal railing on the patio. I got as far as the door and then got hit on the back of the head. I don’t know who hit me from behind, but the back of my head was split open. It didn’t knock me out, but I went down and Sam was underneath me. He had on a pearl gray silk suit, and the blood from my eyebrow was running all over his suit. I had a hold of him by the testicles and the collar and he couldn’t move. That’s when Sinatra came in with his valet, George, the colored boy. They were coming down to join the party.

  The girls were screaming and running around like a bunch of chickens in every direction because nobody knew what was going to happen…George just stood there with the whites of his eyes rolling around and around in his black face, because he knew who Sam was, and nobody ever fought with Sam…Sinatra and George pulled me off Sam, who ran out the door. Then Sinatra called me a troublemaker, and said the gangsters were going to put a hit out on me because of this fight. I told him the only way they’d get me is from a long distance with a high-powered rifle because none of them had the guts to hit me face to face. “I’m not afraid of nothing, Wop,” I said, and he started yelling that I was going to lose the place for him because of this fight. Because of the notoriety he was going to lose all his money. I said, “What do you mean, your money? You don’t have a dime in the place. It’s all Mafia money and you know it.” He and George ran out then, and I left the next day for Nebraska.

  George Jacobs’s account of the incident more or less corroborates Collins’s, except for the Stepin Fetchit eye rolling and a few interesting details. For one thing, “Phyllis was pounding on the manager’s head with her high heel,” the valet writes. Jacobs doesn’t mention Frank’s fears about losing Cal-Neva; instead, he says Sinatra had him drive Mooney to Palm Springs “in one of our low-profile station wagons,” hoping the whole thing would blow over.

  Instead, it blew up. Someone called the police about the fight, the police notified the FBI, and the FBI reported Giancana’s presence at Cal-Neva to the Nevada Gaming Control Board, which promptly began an investigation.

  —

  While Frank was misbehaving in Tahoe, Dean was minding his business in Hollywood. Interviewing Martin on the 4 for Texas set at Warner Bros., the Los Angeles Times’s Don Alpert found the star relaxed, funny, and—in sharp contrast to his good friend’s frequent dyspepsia about making movies—philosophical about the profession. “I call it a wonderful job, working in pictures,” Dean said. “When I finish here, I’ll go to Tahoe with Frank, then I have a whole day off before I go to the Sands in Vegas. Then I do ‘Robin and the Seven Hoods’ with Frank.”

  Robin and the 7 Hoods was to be a gangster comedy, set in Chicago in the 1920s. The irony needn’t be underlined.

  —

  Frank went back to work—grindingly, on 4 for Texas; pleasurably, on new selections for the Repertory Theatre (including, on July 25, his first, magnificent recording of “Luck Be a Lady.” He also cut a couple of new singles on the thirty-first: the charming “Here’s to the Losers” and the less charming “Love Isn’t Just for the You
ng.”

  Then came the black headline in the August 2 Chicago Sun-Times: MOE’S VISIT PERILS SINATRA LICENSE. The story, under the byline of Sandy Smith, detailed Sam Giancana’s late-July sojourn at Cal-Neva and said that the chairman of the Nevada Gaming Control Board, Edward Olsen, had already begun an investigation. The altercation in Chalet 50 was related in detail: Smith had even determined that the person who hit Victor Collins from behind was Cal-Neva’s maître d’, Eddie King. The cat was out of the bag, but in those less interconnected days only in Chicago; the wire services didn’t pick up the story. In the meantime, Frank made headlines of another sort.

  * * *

  *1 In the 2015 HBO documentary Sinatra: All or Nothing at All, Frank junior claimed—contrary to what had long been believed—that he was actually named Francis at birth.

  *2 The memo failed to note that Sinatra’s old pal Luciano was also deceased, having lived in exile for the remainder of his days after his 1946 deportation and succumbed to a heart attack in Naples in January 1962. Among the personal effects found in his apartment was a gold cigarette case with an affectionate inscription from Frank. See Gosch and Hammer, Last Testament of Lucky Luciano, p. 444.

  20

  This is a way of life, and a man has to lead his own life.

  —FRANK SINATRA, IN AUGUST 1963, TO EDWARD OLSEN, CHAIRMAN OF THE NEVADA GAMING CONTROL BOARD

  By early 1963, Reprise Records was losing so much money—a couple of million early-1960s dollars a year—that Frank Sinatra was rumored to be flying to Chicago on weekends to borrow cash from Sam Giancana, and other friends, just to make payroll. Things were so bad that Sinatra was finally forced to change his stance on the brand of music he detested. “I finally went to Frank and said to him, ‘Look, we are going to go bankrupt unless we get into the rock ’n’ roll business and become competitive,’ ” Mo Ostin recalled. “And Frank’s business instincts overcame his emotions. He said, ‘Well, if you feel that strongly about it, then okay, you can go ahead.’ ”