When Sinatra Sang for His Life
The Kennedys, the Mob, and the FBI — the Rat Pack’s legendary 1962 residency at the Villa Venice brought the secret power structure of postwar America under one roof.
Silver Screen Collection / Getty Images
When Frank Sinatra sauntered onstage at the Villa Venice restaurant just before midnight on November 26, 1962, a thin frost coated the windshields of the FBI stakeouts up and down Milwaukee Avenue. It was the biting cold — more than the expected presence of the Feds, more than the evening’s extortionist contract terms — that consummated the abasement of the weeklong Rat Pack residency that kicked off that night.
Sinatra, Dean Martin, and Sammy Davis Jr were long past their days booking the Midwest, never mind in winter. Yet here they were, canceling six-figure shows in Las Vegas and Miami to play a godforsaken supper club on an icy and sewage-streaked bend of the Des Plaines River: a literal backwater.
How the group came to headline the 1962 grand opening of the Villa Venice is a better story than the heist at the center of Ocean’s 11, the 1960 movie that certified Rat Pack ownership of the period’s shoulder-leaning Vegas hepcat style, a celebration of song, booze, broads, and unfiltered cigarettes. Had Warner Bros. turned the Villa Venice residency into that film’s Technicolor sequel, it might have begun with Sinatra entering stage left on opening night, placing his drink on a stool, and snapping down the count on a jazzy cover of the Depression-era swing hit “Goody Goody.” The image would have to freeze after a few bars, capturing the smoldering resentment in Martin’s eyes just as Davis Jr’s voiceover intones, “We were the biggest names in show business. We had the world in our palms and classier places to be. How did we end up playing Nowheresville in November? Baby, it’s a hell of a story.”
Cut to poolside at Sinatra’s Palm Springs estate. It’s 1958. Lounging next to the singer is the junior senator from Massachusetts, Jack Kennedy, whose two younger brothers, Bobby and Teddy, are frolicking in the pool with a group of bikini-clad aspiring starlets in from Los Angeles for the weekend. Or maybe it’s Vegas. It’s hard to say. Sinatra and the Kennedys have romped extensively through both cities since 1954, the year Jack’s sister, Patricia, married the actor and second-tier Rat Packer Peter Lawford. At after-parties and secured hotel floors at the Sands, the Fontainebleau, and assorted private clubs, the women cycling through Sinatra’s world and into the Kennedys’ beds have become a blur. A couple, however, do stand out: Marilyn Monroe, of course, and Judith Campbell, the brunette beauty who became Jack Kennedy’s mistress while also dating Sam Giancana, the only other man for whom Sinatra would sing anywhere, anytime.
Cut again to the same poolside scene in Palm Springs, but it’s 1960, and instead of Kennedy, Sinatra is toasting a balding little round-faced man in a gray porkpie hat and sunglasses. This is Giancana, operating boss of mid-century’s dominant crime syndicate, the Chicago Outfit. The Sinatra-Giancana relationship dates back to the singer’s performance at Lucky Luciano’s famous “Havana Summit” in 1946, which formalized the agenda and power rankings of what was not yet known as the American mafia. Sparkling under the Palm Springs sun are the jeweled friendship rings the two men have gifted each other.
“To the Cal Neva,” they toast. This is the name of their first business partnership, a new resort and casino on the California-Nevada border. It does not occur to Giancana to mention his recent acquisition of a once famous but now faded nightclub in Chicago’s northern suburbs called the Villa Venice.
Sam “Mooney” Giancana earned his nickname as a teenage hoodlum in Chicago’s Little Italy during the 1920s. His taste and talent for extreme violence — what FBI psychologists called a “vicious temperament” and “psychopathic personality” — impressed scouts for the city’s Sicilian-run Black Hand, an operation that straddled organized crime, organized labor, and city and state politics. Giancana’s most important patron wasn’t the local boss, “Diamond” Joe Esposito, but an enforcer Esposito recruited from New York’s Five Points Gang named Al Capone. Capone’s power grew apace with Esposito’s distillery operation, and he brought the young Giancana with him through the ranks, impressed by the teenager’s versatility. “A good wheelman is hard to find, but one with the smarts and guts to kill without question is a gold mine,” Capone told “Machine Gun” Jack McGurn in recommending Giancana. In 1927, at the height of the bootleg wars, Capone tasked his seventeen-year-old understudy with the job of pumping Esposito full of buckshot as the old boss returned from a union meeting.
Thirty-five years later, “Mooney” was one of two dozen nicknames and aliases Giancana used as the Outfit’s operations manager, an executive position held at the pleasure of two shadowy top bosses, Tony “Big Tuna” Accardo and Paul “The Waiter” Ricca. But to Sinatra, he was always just Sam. Where Sinatra was notorious throughout Hollywood for being imperious, the self-anointed Pope of the Rat Pack displayed an eagerness around Giancana that veered toward the pathetic. As he would with Kennedy, the singer not only reveled in the mobster’s company but sought his filial approval and affection.
Following Kennedy’s election to the presidency, this need to prove his worth to both men would nearly cost him his life.
‘Let’s show those asshole Hollywood fruitcakes that they can’t get away with it as if nothing’s happened. Let’s hit Sinatra.’
II.
It’s 1956, and Chicago’s living legend impresario, Albert “Papa” Bouche, is in trouble. Thirty years have passed since the French-Italian immigrant and former beat cop transformed a ramshackle roadhouse in the woods into a tux-and-gown revue for burlesque and stage shows. At seventy-five, the self-declared “papa of all nightlife” wasn’t ready to hang up his hat. Still putting on three shows a night, still hand-selecting his showgirls in private auditions at hotel suites in Havana and New York, he dreamed of a Vegas Villa Venice. But satellite clubs in Miami were expensive failures, and the debts were piling up. Stepping forward to help Bouche out is a buyer named Leo Olsen, a known beard for Sam Giancana. A deal is reached, and the Villa Venice goes dark, just another Outfit property for talking business and the occasional Italian wedding. “Poof goes Chi’s most fantastic showplace,” declares the Chicago Tribune.
Joseph P. Kennedy is a recurring character in mafia memoirs, appearing in autobiographies by Joe Bonanno, Meyer Lansky, and Frank Costello, to name a few. Sam Giancana was shot in the back of the head before he could put his memories on paper, but according to his brother, Chuck Giancana, Sam often recounted stories about running sugar to Kennedy in Boston on behalf of Joe Esposito in the Roaring Twenties. Corroborating the thrust of these claims, if not every detail, are Canadian government records connecting Kennedy to a smuggling operation between British Colombia distilleries and docks on the US side of the Great Lakes.
Not every deathbed story about Joe Kennedy and the mob is true, but it’s hard to believe each one is false, as argued by the Kennedy family court biographer, David Nasaw. There’s no disputing that Kennedy amassed a fortune during the 1920s and somehow emerged from Prohibition in possession of lucrative international liquor import rights. (In fairness, some of his fortune was earned through suspiciously timed stock market bets, including an infamous massive short on the eve of the 1929 Wall Street crash.) Like other bootleggers, Kennedy used his liquor profits to finance an entrance into Hollywood, whose product, escapism, was seen as “the new booze,” in the words of Chicago labor racketeer Murray “The Camel” Humphreys.
By 1930, Kennedy was running three film production companies and making aggressive moves into the theater business. In Sins of the Father, Ronald Kessler recounts how Kennedy paid a teenage girl to file false rape charges against the owner of a theater chain he coveted. When she confided to Kennedy about her guilty conscience, saying she wanted to come clean to the police, she mysteriously fell ill of cyanide poisoning. On her deathbed, she confessed the plot and said Kennedy promised to make her a star.
One California link to Kennedy’s bootlegging past was “Handsome Johnny” Roselli, Chicago’s man in Hollywood. Roselli and Kennedy were often seen playing golf and cards together in the years before the latter’s support for Franklin D. Roosevelt earned him the inaugural chairmanship of the Securities and Exchange Commission in 1932. But even after his move to Washington, Joe Kennedy never sold the family mansion in Beverly Hills. As he moved deeper into politics, he continued mixing socially with gangsters in Hollywood social circles. The enduring Roselli friendship likely played a role in greasing the union and city politics behind Kennedy’s 1945 purchase of Chicago’s then tallest office building, the Merchandise Mart.
In 1947, Jack Kennedy’s election to Congress achieved the first step in realizing his father’s dream of a Kennedy political dynasty. To many, this ambition sounded fantastical for a second-generation Irish Catholic. But it was a fantasy grounded in a singularly sophisticated appreciation for the role organized crime played in American politics. Kennedy knew Joe Esposito’s right to move Cuban sugar was earned by supplying votes and controlling unions for Illinois governor and, later, US senator Charles S. Deneen. At the 1932 Democratic Convention, Kennedy witnessed up close the negotiations that secured the underworld’s help in rounding up delegates in exchange for FDR’s promise (later broken) to quash a crusading New York lawyer’s corruption investigation into city hall and the police. And Kennedy knew, better than most, that the Democratic president his son served in Congress did not emerge in overalls from Missouri’s wheat fields, but was a creation of the mobbed-up Kansas City machine run by Tom Pendergast, who tasked a young Harry S. Truman with collecting weekly payoffs from the city’s brothels.
This understanding, together with the Kennedy family history, explains Joe’s reaction to rumors that reached him in late 1956 concerning Bobby, his strange middle son. Jack Kennedy’s younger brother, it was being said around Washington, was actively recruiting sponsors for a Senate probe into union racketeering. With Jack in the Senate and the 1960 presidential election already in view, Joe Kennedy could imagine few ideas worse than attacking organized crime and the country’s most powerful union, the Teamsters. In his memoirs, Arthur Schlesinger recalls Joe Kennedy being “deeply, emotionally opposed” to the investigation, which he expressed in “an unprecedentedly furious argument” with his son.
In a last-ditch effort to knock Bobby off his path, Kennedy enlisted Supreme Court justice William O. Douglas to convince his son that attacking the mob and the Teamsters was unwise. When the intervention failed, Kennedy watched helplessly as his son pursued a quest he described as an act of “madness.”
III.
For five years after Giancana’s purchase of the Villa Venice, the club is absent from public view. The grand dining room and stage — described in Depression-era ads in Chicago newspapers as offering “magical beauty and sumptuous splendor . . . the gayest evening of your life” — has fallen dusty and out of date. Behind the Villa Venice, the authentic Venetian gondolas imported by Bouche for his club’s signature gimmick are mostly kept at dock, activated only for the occasional Outfit social event. Not that demand is high. The Des Plaines River now resembles the Ganges more than it does a Venice canal. The uniformed pilots chew lemon and light scented candles to hold back the smell of sewage in the water.
It is customary for books about the Kennedys to note the religious fire that animated Robert F. Kennedy. His mother, Rose Kennedy, assumed he’d channel it into the church. The Washington socialite Alice Roosevelt Longworth observed in him the psychological profile of “a revolutionary priest.” This assessment is borne out in Kennedy’s decision to work, fresh out of law school, as a Red-hunting aide to Wisconsin senator Joseph McCarthy.
A thirty-one-year-old Robert Kennedy deployed the same Manichaean vocabulary in his opening statement as chief counsel to his legal-political brainchild, the Rackets Committee, formally known as the Senate Select Committee on Improper Activities in Labor and Management. The committee’s subject, said Kennedy in January 1957, was a “conspiracy of evil” requiring a purifying exorcism. Over the next two years, Kennedy would direct more than 250 investigations that named thousands of individuals suspected of helping to fix lucrative contract negotiations and turn the Teamsters’ $40 million pension fund into a honeypot for the mob.
Throughout the hearings, Bobby Kennedy described his targets in terms that leaned crudely on new ethnic anxieties around Italian Americans and organized crime. He opened the hearings by reading aloud the names of one hundred Italian Americans that he described as having the physical appearance of “Capone’s men. They are sleek, often bilious and fat, or lean and cold and hard. They have the smooth faces and cruel eyes of gangsters; they wear the same . . . sickly-sweet-smelling perfume.”
On the morning of June 5, 1959, Kennedy found himself opposite a cruel-eyed witness who really was one of Al Capone’s men. Sam Giancana entered the Senate chamber in a quasi costume — wig, fedora, and sunglasses — that nodded to his yearlong evasion of subpoena-bearing agents. Like every other suspected mobster that testified before Kennedy, Giancana pled the Fifth to each question. In the middle of what had become a familiar routine, Giancana audibly chuckled, causing Kennedy to bark, “I thought only little girls giggled, Mr Giancana.”
According to Chuck Giancana, his brother described the laughter as a result of imagining the Kennedys during one of their benders in mobbed-up Vegas hotels. “It was all so funny,” he remembered Sam saying. “What a bunch of fuckin’ hypocrites.”
Though technically a member of the Rackets Committee, Jack rarely attended the hearings. Like his father, the older son had no desire to incur the mob’s wrath or risk losing labor support for his upcoming presidential campaign. Indeed, no matter how damning the evidence against them, the Teamsters skillfully depicted Bobby Kennedy as a spoiled rich kid attacking blue-collar symbols of a hard-won postwar prosperity. As itemized in a poem published by the International Teamster, Teamsters members rise before dawn to deliver “A vial of penicillin for a sick child / A frilly gown for a young girl’s first date / A loaf of bread for a hungry miner . . . A new way of life for 170 million people.”
Among the millions of Americans who seemed to agree with the Teamsters was J. Edgar Hoover, who declined to pursue any of the committee’s cases and left an outraged Bobby Kennedy to settle for a reform bill that toughened transparency requirements in union finances.
For Joe Kennedy, the Rackets Committee’s anticlimactic conclusion in March of 1960 arrived just in time. There were primaries to win — and a naive son’s mess to clean up.
Not every deathbed story about Joe Kennedy and the mob is true, but it’s hard to believe each one is false.
IV.
In springtime, 1962, the decision to renovate the Villa Venice is made. Giancana authorizes $250,000 to be spent remodeling the exterior, the dining area, and the ballroom. No cut corners. The boss takes a personal interest in the details: plush burgundy carpeting, satin-draped ceilings, and new uniforms for the gondoliers. The renovation extends to a wooded lot next to the Villa Venice, owned by another Outfit-run establishment, the Flamingo Motel. Here Giancana oversees the construction of the Villa Venice casino, housed in an insulated semicircular Quonset hut. Elaborately camouflaged with old trucks and rusted road machinery, come November, it will house a gaming den replete with coat check, bar, roulette wheels, tables for dice and blackjack, and a cashier’s cage stocked with Vegas-style chips racked under a sign reading “no cash bets.” As in Las Vegas, this will be the real action, the hook, and the singers next door the bait.
Like the story of Joe Kennedy’s bootlegging career, the tale of the old man’s mob outreach in 1960 depends on who you choose to believe.
One version is found in Tina Sinatra’s scripted 1992 CBS miniseries about her father’s life, which she says had his input and approval. The account, which she described again in a 2000 interview with 60 Minutes, has Joe Kennedy contacting Sinatra in early 1960 concerning his desire to secure the election aid of the major syndicates, Chicago in particular, in exchange for gratitude from a Kennedy White House that would rein in Bobby.
“A meeting was called, a private meeting over lunch, I believe at Hyannis,” said Tina. “Dad hadn’t been to the house before. Joe said, ‘I believe that you can help me in [West] Virginia and Illinois with our friends. I can’t approach them, but you can.”
Other accounts allege Kennedy made direct contact with underworld figures, while also using Sinatra as a trusted go-between. In The Outfit, Gus Russo quotes multiple sources who claim to have known about or attended a luncheon at Felix Young’s restaurant in Manhattan on February 29, 1960, convened for Kennedy’s benefit by his old Hollywood friend Johnny Roselli. Mario Brod, a longtime CIA cutout and mob liaison, told Russo that Kennedy’s pitch enraged Chicago’s top political fixer, Murray Humphreys, who warned his colleagues against trusting the Kennedys. Then there is the sensational claim of Chicago mob lawyer Robert J. McDonnell, found in Seymour Hersh’s Dark Side of Camelot, that Kennedy and Giancana hashed out an arrangement face-to-face in Chicago, in a meeting arranged by William J. Tuohy, a powerful Chicago judge and old Kennedy family friend.
Whatever the details of Kennedy’s offer — who communicated it, when, and how — the basic outline is confirmed in publicly available fragments of the FBI’s vast wiretap archive from the period: Joe Kennedy wanted the Outfit to help deliver money and votes, and with Sinatra’s help, he convinced the bosses that their assistance would not be forgotten and a line of communication would be maintained. In his memoir, Man Against the Mob, Giancana’s longtime nemesis in the FBI’s Chicago office, William F. Roemer Jr, also claims to have heard a classified wiretap — circulated within the agency on a need-to-know basis during the 1960 election — in which Giancana links Outfit election work to his mounting frustration with constant federal tails and investigations. If Kennedy’s help could reduce the heat a bit, it would be worth it. Sinatra, meanwhile, vouched for the Kennedys, touted his access to the family, and promised to hold Kennedy Sr to his word.
Chicago and Hyannis reached an understanding just in time for the West Virginia primary, a crucial test of Kennedy’s electability. If the Irish American senator from Massachusetts could win over hardcore Protestants in the hollers of McDowell County, the Catholic question would be settled.
As Jack Kennedy and his father campaigned through the Mountain State with Jimmy Roosevelt — telling rapturous lies about FDR’s affection for the elder Kennedy — Outfit lieutenants helped the campaign distribute millions of dollars to local officials. An FBI bug picked up one of them, Paul “Skinny” D’Amato, discussing his arrival from Chicago with suitcases full of cash in his car trunk, some of which he used as payola to ensure West Virginia jukeboxes played his other cargo: boxes of vinyl 45s containing the Kennedy campaign’s Sinatra-sung theme song, “High Hopes.” Kennedy won the state with 61 percent of the vote.
V.
November 26, 1962. The casino has been operating for two weeks, with Eddie Fisher warming up the stage for Sinatra, Martin, and Davis Jr, whose first Rat Pack show is tonight, marking the sold-out official grand reopening of the Villa Venice. They’ve come from around the Midwest — regional bosses, underbosses, associates, henchmen, hangers-on, and not a few moneyed straights titillated by the prospect of gambling with real chips, real gangsters, and taking an unlikely draught of A-list glamour in the north Chicago suburbs. Across the street from the blinking neon marquee on Milwaukee Avenue, the Feds empty film rolls and break pencils trying to record the plates of every arriving tail-finned Cadillac DeVille.
Giancana is greeting guests under the canopied entrance and taking compliments. The “new” Villa Venice takes guests back, they say, to the good old days, when the Venice was pure class and had the most beautiful dancers this side of the Tropicana. Waiters — who know to address Giancana as “Mr Flood” — show guests to candlelit tables centered with maidenhair ferns, where their $12.50 ticket is good for one show, one drink, and a chicken Vesuvio dinner.
Giancana settles in the back of the dining room, flanked by a local underboss, Felix “Milwaukee Phil” Alderisio, and a sadistic enforcer, Willie “Potatoes” Daddano, known for deploying ice picks and blowtorches in his heavy work. At the front of the room, the best seats in the house are occupied by Outfit vice boss Jimmy “The Monk” Allegretti and an aging box-faced enforcer named Marshall “Johnny Shoes” Caifano. Dead center before the stage is a table shared by Giancana’s younger brother, his personal bodyguard, Butch Blasi, and gaming lieutenant Rocco “Parrot Nose” Potenza. Later that night, Anne Marie Giancana whispers to her husband that they’re sitting so close, she can smell Sinatra’s cologne.
Jack Kennedy’s narrow victory over Richard Nixon in November validated his father’s strategy of enlisting the Outfit. The election was called after Illinois’s twenty-seven electoral votes went to Kennedy by a margin of just ten thousand ballots. While the Outfit’s impact in Illinois is a matter of debate, and almost certainly overshadowed by the role of Richard J. Daley’s political machine, there is evidence the mob held up its half of the deal, in the Prairie State and beyond.
The most curious exhibit is the running log kept during the summer and fall of 1960 by Jeanne Humphreys, wife of the Outfit’s longtime political fixer, Murray, who advocated against helping the Kennedys. In contemporaneous diaries, Humphreys details two extended stays at the Chicago Hilton — one just before the convention and the second in the run-up to Election Day — during which her husband met with visiting political and union officials from around the country. “It’s ironic,” reads one entry, “that most of the behind-the-scenes participants in the Kennedy campaign could not vote because they had criminal records.” Humphreys’s account is backed up by FBI surveillance records detailing a flow of visitors to their hotel room.
Whatever the Outfit’s contribution, the Chicago boss was convinced he had crowned a king. Judith Campbell, the mistress Giancana shared with the president-elect, recalled in her memoirs the mobster telling her, “Listen, honey, if it wasn’t for me, your boyfriend wouldn’t even be in the White House.”
Sinatra, meanwhile, believed he possessed the ears and good graces of an incoming president and the syndicate that helped him win the highest office. On the blizzardy evening of January 19, 1961, the singer hosted a star-studded black-tie inauguration gala that ended with Sinatra singing a medley with Milton Berle, Gene Kelly, Ella Fitzgerald, and Nat King Cole. They closed the finale with a five-part harmony version of “High Hopes,” the Kennedy campaign song Sinatra had repurposed from a 1959 musical titled, of all things, A Hole in the Head.
‘I believe that you can help me with our friends. I can’t approach them, but you can.’
VI.
The night of the grand opening, an FBI stakeout sees Sinatra and Dean Martin enter the Villa Venice with Joseph Fischetti, a former Outfit underboss now residing in Miami as part owner of Puccini’s Restaurant. Martin has long known Fischetti and other Outfit figures, all the way up to Paul Ricca and Tony Accardo, the shadowy top bosses behind Giancana’s throne. But Martin doesn’t share his friend Frank’s “hoodlum complex,” avoiding the company of gangsters whenever he can.
Minutes after being introduced — “Direct from the bar, Dean Martin!” — he indulges this contempt as much as he dares, drawing attention to the sharkskin elephant in the room. He begins to sing “The Lady is a Tramp” but ad-libs over the familiar melody, singing, “I love Chicago / It’s carefree and gay / I’d even work here, without any pay / I’ll lay you odds, it turns out that way / That’s why this gentleman is a tramp.”
The room erupts in laugher, some of it nervous. The tittering is more hesitant a few minutes later, when Martin shushes the crowd, points to the club’s penthouse office, and declares, “Don’t you know there’s a gangster sleeping up there?”
The announcement of Robert F. Kennedy’s appointment to the post of attorney general confused a lot of people. Even within the family’s circle, people whispered that an assistant secretaryship of defense was more appropriate. But Joe Kennedy was not one of the whisperers. Having achieved his dream of siring a president, Kennedy Sr appeared unbothered by the possibility that his son might resume his furious pursuit of organized crime. If he had misgivings, he kept them private.
As the country’s top law enforcement official, Bobby Kennedy immediately reopened the case files compiled by the Rackets Committee. When J. Edgar Hoover blocked his proposal for a national crime commission, he coordinated directly with federal agencies, primarily the IRS, to win nearly one hundred mob convictions in his first year — five times as many as the last year of the Eisenhower administration. Though successful, Kennedy’s targeting of the major bosses — taunting Miami’s Santo Trafficante Jr and New Orleans’s Carlos Marcello with tax bills and deportation threats — began to generate alarm within the Kennedy orbit. In Mafia Summit, Gil Reavill writes that one close family friend expressed worry that the Kennedy brothers “didn’t really know who they were dealing with.” Another Harvard friend who worked with steel unions relayed a warning that Bobby should “back off or he’ll end up in the river.”
The FBI’s surveillance operation also captured the mob’s assurgent impatience with the Kennedy White House. Outraged over Kennedy’s threat to deport him, Marcello asked Trafficante why his friend Sinatra wasn’t demanding Joe Kennedy bring his kid into line. Adding to the bosses’ confusion over ongoing persecution by the FBI was their secret partnership with another branch of the government, the CIA, with whom they were working to plot the assassination of Fidel Castro. (The alignment of interests — and Kennedy hatred — between the mob and the intelligence establishment is its own story, one told with authority in David Talbot’s The Devil’s Chessboard.)
One of the foreign-born mobsters threatened by Bobby Kennedy’s deportation strategy was Joe Kennedy’s old Italian-born friend Johnny Roselli. Shorn of the illusion that Sinatra or anybody else could rein in Bobby, Roselli became an early advocate for tougher measures. An FBI phone tap caught him telling Giancana in 1961, “[The Kennedys] only know one way. Now let them see the other side of you.”
Roselli’s position became conventional underworld wisdom on April 4, 1961. That morning, federal agents arrested Marcello in downtown New Orleans, denied his request to speak to his lawyer, and placed him in handcuffs on a one-way flight to Guatemala, where he had once secured a fraudulent passport. Marcello returned to New Orleans that spring with a vengeance that ran emotionally hot and operationally cold. An FBI informant who attended a September 1961 meeting at Marcello’s farmhouse reported the boss using a Sicilian curse that equated the attorney general to “a stone in his shoe.”
That same month, Jack Kennedy signed three interstate anti-crime acts based on Bobby’s investigations. The bills — outlawing the use of phones and wires to transmit sports bets as well as the interstate transportation of gambling equipment — threatened major sources of revenue for the syndicates.
The stakes were highest for the Chicago Outfit, which controlled the biggest nationwide sports betting and numbers operations. Like Marcello, Giancana had come to view his compact with Kennedy as a deal gone bad. Murray Humphreys had been right. And if Humphreys was right, that made the eager-to-please Sinatra wrong.
But was he useless?
VII.
Giancana isn’t in the room to hear Martin’s jokes at his expense. He’s with his gaming lieutenant, Rocco Potenza, in the casino next door, which is filling up with gamblers steered by Outfit soldiers working the Villa Venice dining hall. Limousine shuttles make the short loop between the club and the gambling hut in the woods. By 1 a.m., there are so many cars outside the club and the neighboring casino that Outfit chauffeurs are forced to take turns directing traffic, shivering against the cold.
Following the September signing of Kennedy’s anti-crime bills, Sinatra finally paid a visit to Hyannis Port. The substance of that conversation is not known. A few days later, he visited the White House with his fellow Rat Packer and the president’s brother-
in-law, Peter Lawford. It was then that Sinatra communicated the Outfit’s displeasure directly to Bobby Kennedy. We know the details of Sinatra’s feeble effort because he described them to Johnny Roselli, who relayed them to Giancana in a call recorded by the FBI.
“He says, ‘Johnny, I took Sam’s name, and wrote it down, and told Bobby Kennedy, ‘This is my buddy, this is what I want you to know, Bob,’” Roselli tells Giancana. “Between you and I, Frank saw Joe Kennedy three different times. He called him three times. He [Frank] says he’s got an idea that you’re mad at him. I says, ‘That, I wouldn’t know.’”
Sinatra was right about Giancana’s anger, but he remained naive about his position with the Kennedys. Reports of the singer’s mob ties had begun popping up in the media, leading to an unwelcome exchange during a White House press briefing. The breaking point came in February 1962, when the FBI presented Bobby Kennedy and a White House aide, Kenneth O’Donnell, with evidence that Sinatra, a recent guest at 1600 Pennsylvania Avenue, was routinely socializing with subjects of active Justice Department investigations. The dossier also contained a potentially disastrous revelation: Judith Campbell’s phone logs showed Kennedy’s mistress placing alternating calls to the White House and to Sam Giancana’s home. The file further quoted Sinatra in Vegas clubs publicly discussing Campbell as the “broad shacking up with John Kennedy in the East.”
The Kennedys dispatched Peter Lawford to inform Sinatra the president was canceling a planned winter stay at his Palm Springs estate, where the singer had constructed a presidential compound with helipad. Rubbing salt into the wound, Kennedy would instead be staying with Bing Crosby.
“Frank was livid,” Lawford recounted to Sinatra biographer Kitty Kelley. “He called Bobby every name in the book, and then rang me up and reamed me out again . .&npsp;.. He was in a frenzy.” According to Sinatra’s valet, the singer then “went outside with a sledgehammer and started chopping up the concrete landing pad of his heliport.”
Sinatra still did not understand that he had more serious problems than a presidential family slight. Two thousand miles away, Giancana was deciding his fate in conversation with an unforgiving underboss named Johnny Formosa. The discussion took place in the Armory Lounge, an Outfit hideaway just north of Chicago, the walls of which the Feds had recently bugged.
When Giancana cursed Sinatra for promising things he couldn’t deliver, Formosa proposed making a lesson of him and his crew.
“Let’s show ’em,” said Formosa. “Let’s show those asshole Hollywood fruitcakes that they can’t get away with it as if nothing’s happened. Let’s hit Sinatra. Or I could whack out a couple of those other guys. [Peter] Lawford and that [Dean] Martin, and I could take the nigger [Sammy Davis Jr] and put his other eye out.”
There was a famous Chicago precedent for disciplining entertainers. In 1927, one of Al Capone’s favorite singers, Joe E. Lewis, disobeyed his command and sang at an unaffiliated night club. In response, Capone dispatched three enforcers to Lewis’s hotel room. At their head was a nineteen-year-old Sam Giancana, who slit the singer’s face and neck open, all but severing his tongue. Remarkably, Lewis rebuilt his career and sang again, a comeback story dramatized in the 1957 film The Joker Is Wild. Starring in the role of Joe E. Lewis was none other than Frank Sinatra.
“No,” Giancana told Formosa in the Armory Lounge. “I’ve got other plans for them.”
Visions of a renovated Villa Venice were beginning to percolate in Chicago.
VIII.
An article in the November 30, 1962, edition of the Chicago Daily News reports, “Since the new star policy at the Villa started off, a heavy toll has been levied at the hut on the patrons. Individual losses of as much as $25,000 have been reported.”
Giancana dismisses the article and orders the casino to stay open. Three nights later, amid rumors that a police raid is imminent, an Outfit lookout named Joe Iacullo spots another reporter outside the casino, this one asking about Outfit figures by name. A little after 2 a.m. on December 4, Giancana gives the order to switch on a floodlight that illuminates the casino’s junk-strewn facade, signaling an end to the games.
Estimates on Giancana’s tax-free killing during the casino’s operation range as high as $3 million. Whatever the final haul, it wipes Sinatra’s debt clean.
Sammy Davis Jr and Dean Martin are ready to head for the airport and forget the whole episode. But the FBI is waiting for them at their hotel. When agents press Davis Jr about why he canceled lucrative Vegas shows to play for free in Illinois, he leans back in his chair and says, “Baby, let me say this. I got one eye, and that one eye sees a lot of things that my brain tells me I shouldn’t talk about. Because my brain says that, if I do, my one eye might not be seeing anything after a while.”
John F. Kennedy was assassinated one year minus four days after Sinatra took the stage at the grand opening of the Villa Venice. The man accused of firing the fatal shots, Lee Harvey Oswald, was linked to Carlos Marcello and, very possibly, a CIA operation related to Cuba. The man who killed Oswald in jail, Jack Ruby, née Jacob Rubenstein, was a Chicago foot soldier sent to Dallas to help with the Outfit’s growing Texas operations. Following his brother’s death, Bobby Kennedy lost all interest in his mob crusade.
Sinatra sought a family invitation to the funeral but was blocked — “He’d already been too much of an embarrassment to the family,” said Lawford. The singer’s misogynistic saloon act was also becoming an embarrassment. The week of the Villa Venice engagement, the Beatles had their first number-one hit in the United States with “Love Me Do,” signaling the start of Sinatra’s swift cultural demotion. He did not take it well. In 1965, Gay Talese would capture the former Chairman of the Board at a private Los Angeles club, drunkenly berating the young screenwriter Harlan Ellison for his leather boots and shaggy sweater, then yelling at the manager, “I don’t want anybody in here without coats and ties!”
That same year, 1965, Paul Ricca and Tony Accardo stripped Giancana of his power. They had already quashed what they considered reckless plans for the Villa Venice following the profitable Rat Pack shows — Jimmy Durante and Dinah Shore residencies, more gambling — and now decided that Giancana should leave the country. This the newly defrocked boss did with haste. Giancana was living in a compound south of Mexico City when the wire came through for a six-figure payout on a Lloyd’s of London insurance policy. The Chicago dailies had barely noticed when, on the night of March 4, 1967, the shuttered Villa Venice caught fire and burned efficiently to the ground.
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CONTRIBUTORS
Alexander Zaitchik is a freelance journalist living in New Orleans. His next book, Owning the Sun: A People’s History of Monopoly Medicine, from Aspirin to Covid-19, will be published by Counterpoint in 2022.