“I own Chicago. I own Miami. I own Las Vegas,” Giancana states to an FBI agent. Senator Jack Kennedy’s efforts to break this hold have made him the chamber’s second-ranked Democrat on Labor. He’s joined the Select Committee on Improper Activities in the Labor Management Field, or Rackets Committee, supported by the group’s chief legal counsel—Jack’s younger brother Bobby.
In June 1959, Giancana and thirty-four-year-old Bobby Kennedy have a headline-making confrontation when Giancana is called to testify before the committee. Although Giancana has taken the Fifth Amendment, a legal protection against self-incrimination, Bobby reels off antagonistic questions for the record.
Since then, Giancana has been quietly building relationships with politicians and law enforcement and is well aware that an alliance with the next potential occupant of the Oval Office might protect his “outfit” from federal investigations.
Joe wants to capitalize on Giancana’s power over Illinois unions, whose votes in Cook County he believes are key to Jack besting the Republican presidential front-runner, Vice President Richard Nixon, in this winner-take-all state in the Electoral College.
McDonnell, who waits with Judge Tuohy in the jury box during Joe and Giancana’s meeting, later reveals to the investigative reporter Seymour Hersh how the handshake deal was executed. “There was no ballot stuffing…They just worked—totally went all out. He [Kennedy] won it squarely, but he got the vote because of what [Giancana] had done.”
The mobster shifts easily between the hard-driving urban labor contingent and the glitzy denizens of the Las Vegas strip, where from the shadows he controls such top-name casinos as the Sands and the Riviera. Giancana “had the most perfectly manicured hands and nails I had ever seen,” observes George Jacobs, who worked as Frank Sinatra’s valet.
Giancana’s close pals with Sinatra, the biggest headliner on the strip. Ol’ Blue Eyes, Frank Sinatra, is the leader of the Rat Pack, a rotating cast of singers and actors that at that time included Dean Martin, Sammy Davis Jr., and Joey Bishop. The British actor Peter Lawford is a recent addition, broadly dismissed as “the least talented member of the Rat Pack,” but the FBI has a theory about Lawford’s inclusion. Peter Lawford is married to a Kennedy sister: Patricia. Pat and Peter’s 1954 wedding had been a huge social event, attracting more than three thousand spectators outside St. Thomas More Cathedral in New York City. Rumors would also later surface of an affair between Pat and Sinatra.
But Sinatra is interested in a different Kennedy—Jack—and only Lawford can help him connect. “A well-known movie actor has been cultivated by Sinatra and they are now apparently close associates,” a New Orleans special agent for the FBI reports to Director J. Edgar Hoover in March 1960, the month before the Illinois primary.
“There was a joke at the time that ended up having a lot of truth to it,” cultural historian Steven Watts writes, “that in a way, Kennedy wanted to be Sinatra and Sinatra wanted to be Kennedy.” Judith Campbell Exner, a dark-haired Californian whose beauty “was in the Elizabeth Taylor category,” according to a Hollywood reporter, saw it happen firsthand. “They seemed to have a genuine mutual admiration society; Frank was in awe of Jack’s background and his power as [future] President and Jack was mesmerized by Sinatra’s swinging lifestyle.”
Even more mesmerizing to Jack? Judith Exner herself.
* * *
Sinatra is holding court at his usual table at the Sands Lounge in Las Vegas, in February 1960. Among the entourage reveling in the success of yet another sold out Rat Pack show is the twenty-five-year-old Exner, who listens attentively to Sinatra—whom she’d briefly dated in 1959—until she notices two new faces around the table. She doesn’t know that Jack Kennedy and his brother Ted are in politics until Sinatra introduces Jack as Senator Kennedy.
Nominally, Jack and Ted—now twenty-eight and his brother’s campaign manager for the western states—are collecting advice from Hollywood influencers. Jack’s poll numbers have been flagging in California, and the Democratic National Committee’s nomination convention is set for July in Los Angeles. The Hollywood publicist Jim Mahoney, who represents Sinatra and Lawford, remembers strategizing, “Do a ‘Youth for Kennedy’ operation…Get the veterans behind him. He’s got to do something here in California or he’s in big trouble.”
What the senator does do is ask Judith Cambell Exner to a poolside lunch. They talk for hours, Jack’s trademark sense of humor revealing itself in his reaction to Exner’s confession that his younger brother Ted had made a failed pass at her the night before. “That little rascal. You’ll have to excuse his youthful exuberance,” he laughs.
“[Jack] seemed anxious to get together again. I was elated, almost giddy,” Exner later tells People magazine.
A month of daily phone calls—“Jack was the world’s greatest listener,” Exner writes in her 1977 autobiography, My Story—culminates in a passionate meeting at the Plaza Hotel in New York, the night before the March 8, 1960, New Hampshire primary. “It was amazing to me that he could be so relaxed on the eve of the first primary of his presidential campaign but unbelievably, he didn’t mention New Hampshire once during our entire night together. The next morning, he sent me a dozen roses with a card that said, ‘Thinking of you…J.’”
Jack’s not the only one thinking of Exner. In April, Sinatra also introduces her to his good friend “Sam Flood,” an alias of Sam Giancana’s. Incredibly, Exner begins carrying on two simultaneous affairs, one with a presidential hopeful, and one with the “Chicago Godfather.”
She also starts carrying currency—hard cash and secret information—between her two lovers. “I feel like I was set up to be the courier,” she explains to People magazine. “I was a perfect choice because I could come and go without notice, and if noticed, no one would have believed it anyway.”
One such operation involves a plan to quash the mounting threat in West Virginia from rival Democratic candidate Senator Hubert Humphrey of Minnesota, who has been benefitting from growing voter concern over Kennedy’s Catholic faith.
“I think he [Giancana] can help me with the campaign,” Jack tells Exner, and puts her on a train to Chicago with a shadowy “protector” who may have been a Chicago political operative, as well as a satchel full of cash—enough to secure a meeting at the Fontainebleau Hotel in Miami Beach on April 12.
The gangster, the senator, and Exner—and likely the new mink coat she paid for with the two thousand dollars in cash Jack gave her before the train trip—are all present at the Miami Beach meeting, though she acknowledges, “The plans had all been made without me, way ahead of time.”
A key part of those plans is to capitalize on a unique West Virginia campaign law that favors well-financed field operations. Paying staffers and voters money to cast their ballots is allowed, and the Kennedy dollars are flowing.
On May 10, Jack wins over 60 percent of the vote, forcing Humphrey out of the race.
Reporters laugh along with him as Jack jokes, “I just received the following wire from my generous Daddy; Dear Jack, Don’t buy a single vote more than is necessary. I’ll be damned if I’m going to pay for a landslide.”
That many of them probably know the truth in that statement is moot.
In July, Jack accepts the Democratic Party’s presidential nomination and addresses a rapt audience at the national convention in Los Angeles, stating that he sees the country’s future “on the edge of the New Frontier—of the 1960s—a frontier of unknown opportunities and perils—a frontier of unfilled hopes and threats.”
Unknown. Unfilled. Perils. Threats. How closely the dark elements of Jack’s predictions would parallel his own last days.
Sinatra watches the nomination alongside Jack’s father, Joe; Jack’s brother Bobby; and Jack’s brother-in-law Peter Lawford—the Rat Pack now the “Jack Pack”—and considers himself one of them, stating, “We’re on our way to the White House.” He’s right.
On November 8, voters tip the popular vote to Jack by the narrowest
of percentages, 49.7 to 49.5 percent—a 118,550-vote margin out of 69 million votes cast. In the Electoral College, he wins 303 to 219.
That fall of 1960, Rose Kennedy writes in her diary, “I doubt [Joe Sr.] will ever get credit for the constant, unremitting labor he has devoted to making his son President.”
But it’s the mobster Giancana who takes credit, boasting to Exner, “Your boyfriend wouldn’t be president if it wasn’t for me.”
Chapter 16
John F. Kennedy takes office in the dawn of the television age, the first occupant of the Oval Office to regularly broadcast his press conferences live.
He’d been hugely successful during the first-ever televised presidential debate against Nixon, where his image of youth and vigor dominated over the older man. It didn’t matter how ill Jack truly was—the important thing was that he looked healthy and telegenic.
Perhaps influenced by his mother’s lifelong criticisms of his sloppy appearance, Jack knows the value of presentation. “Rather vain” was Jackie’s initial impression of Jack, according to Bouvier cousin John Davis’s recollection. “She talked about how he had to have his hair done all the time, how he had to always look just right.”
Norman Mailer saw JFK as “Superman” with a “jewel of a political machine, all discipline and savvy and go-go-go.” He “had the deep orange-brown suntan of a ski instructor, and when he smiled at the crowd his teeth were amazingly white and clearly visible from a distance of 50 yards. It was a hero America needed, a hero central to his time.”
Television audiences would never see that hero’s utter reliance on his valet, George E. Thomas, who called the president “John F.” Thomas not only plans the president’s wardrobe—up to four clothing changes per day—but helps him dress. Due to lingering pain from his back injuries and osteoporosis, Jack needs help getting into his back brace and shoes, and even with navigating stairs.
During the 1960 presidential campaign, Kennedy sought out Dr. Max Jacobson—“Dr. Feelgood” to his patients—for relief from pain and exhaustion. Once in the White House, Kennedy’s prescription list becomes so extensive that staff maintains the crucial “Medicine Administration Record.”
True to the Kennedy ethos, one is never enough. “Doctors came and went around Kennedy,” writes biographer Richard Reeves. “In a lifetime of medical torment, Kennedy was more promiscuous with physicians and drugs than he was with women.”
But no amount of physical suffering deters him from implementing his ambitious social agenda. Plans to create the Peace Corps and attack poverty were in line with campaign promises, but not the idea that New Frontier would extend into outer space. On May 25, 1961, in a joint congressional session on “Urgent National Needs,” the president sets an astonishing benchmark, saying, “I believe this nation should commit itself to achieving the goal, before the decade is out, of landing a man on the moon and returning him safely to Earth.”
But his lofty goals are quickly, and repeatedly, interrupted by Cuban crises. The flash of the new and the blindness of inexperience soon collide in the first serious crisis of the Kennedy administration. In January 1959, two years before Jack’s inauguration, General Fulgencio Batista’s American-friendly government in Cuba fell to thirty-two-year-old revolutionary Fidel Castro. The new self-appointed prime minister declares himself a Communist and signs a series of pacts with Soviet premier, Nikita Khruschev.
A CIA operation funded by Kennedy’s predecessor, President Dwight D. Eisenhower, identified former Cubans exiled to Miami when Castro took power, more than fourteen hundred of whom join top-secret “Brigade 2506” in 1961 and are taken to receive extensive training from US military special forces.
The three-part plan calls for the brigade to attack Castro on a Cuban beach known as the Bay of Pigs—where Castro is known to fish—followed by an airstrike and then a combined attack. The assumption is that once Castro is out of the picture, the Cuban people will turn to a more US-friendly leader.
Democrat and foreign policy expert Dean Acheson warns the president that “this was a disastrous idea.”
It was.
The mission begins—and ends—on April 17, 1961. The brigade begins their attack, but at the last minute, Kennedy withholds US air support for fear of reprisal from the United Nations, leaving the exiles trapped at the landing site. Castro quickly activates his militia to kill more than a hundred, and imprisons the rest of Brigade 2506 for the next twenty months before releasing them in exchange for more than fifty million dollars in American food and medical supplies for Cuba—and the integrity of the Kennedy administration.
The Bay of Pigs fiasco shatters the president’s confidence. “I have had two full days of hell—I haven’t slept—this has been the most excruciating period of my life,” he tells his legal adviser Clark Clifford. “I doubt my presidency could survive another catastrophe like that.”
Indeed, international relations between the United States and Cuba and their powerful ally, the Soviet Union, only get worse from there, leading to the Cuban Missile Crisis, when Kruschev establishes plans to place nuclear missiles in Cuba to defend the island.
It’s another test of the Kennedy administration, and at a tense cabinet meeting in 1962, when it appears that the United States and the Soviet Union are on the brink of nuclear war, Air Force Chief of Staff General Curtis LeMay tells Kennedy, “You’re in a pretty bad fix, Mr. President,” to which Kennedy shoots back, “You’re in there with me.”
Jackie chimes in with a romantic view of these dark days, though her tender feelings weren’t made public for decades. “If anything happens, we’re all going to stay right here with you,” Jackie told her husband, according to interviews she did with Schlesinger in 1964 (unreleased until 2011).
Thankfully, the countries are able to come to a disarmament agreement, and the president comes out of the crisis with his reputation relatively intact.
Bobby Kennedy, on the other hand, has already had his own reputation stung by accusations that nepotism landed him the attorney general position at just thirty-five years old. “I can’t see that it’s wrong to give him [Bobby] a little legal experience before he goes out to practice law,” Jack quips, but it’s Bobby who takes the hits.
In the meantime, he’s already concocted another plan to dislodge Castro from power. In a November 1961 meeting at the White House, Bobby writes in his notebook, “My idea is to stir things up on the island with espionage, sabotage, general disorder, run and operated by Cubans themselves with every group but Batistaites and Communists. Do not know if we will be successful in overthrowing Castro but we have nothing to lose in my estimate.”
Operation Mongoose, a multiagency covert operation, is launched under Bobby’s oversight. “Get rid of the Castro regime, quote-unquote,” is the way the CIA officer Sam Halpern describes his orders—and when he asks for clarification on what “get rid of” means, he is told, “Sam, use your imagination.” What defies imagination, given RFK’s history with prosecuting the mob, is the recruitment of the Mafia. With Castro’s seizure of power, the Mafia has lost their lucrative casino businesses in Cuba, and they’re eager to assist.
Judith Exner is again tapped as a courier between Jack and Giancana, including helping to arrange a meeting between them in Chicago in her hotel suite, where she exiles herself to the bathroom while the president and the mob boss discuss strategy in the bedroom.
“I thought I was in love with Jack. He trusted me and I was doing something important for him,” Exner later reflects. “I guess I felt I was doing something important.” She claims not to have known what that something was, though, until over a decade later: “It finally dawned on me that I was probably helping Jack orchestrate the attempted assassination of Fidel Castro with the help of the Mafia.”
The Mafia’s plans ranged from sprinkling a CIA poison on Castro’s food to an exploding cigar and poison flowing from a pen. But the assassination plans don’t go anywhere, and are eventually superseded by the Cuban Missile Crisis.<
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President Kennedy never fulfills his father’s promise of protection for the mob from the Oval Office. Instead, his brother Bobby Kennedy, the attorney general, doubles down on his pursuit, making it his important mission to obliterate the American Mafia.
Giancana fumes, “My millions were good enough for ’em, weren’t they? The votes I muscled for ’em were good enough to get Jack elected. So now I’m a fuckin’ greaseball, am I?” according to Chuck Giancana, author of Double Cross, a biography of his mobster uncle. “Well, I’m gonna send them a message they’ll never forget,” Giancana threatens.
Menacing words like these are what keep Judith Exner silent for the next twenty-five years. “I’ve gone to great lengths to keep the truth from ever coming out, which is probably the only reason I’m alive today,” she tells People magazine in 1988. “I lied [to the Senate Select Intelligence Committee that investigated “Operation Mongoose” in 1975] when I said I was not a conduit between President Kennedy and the Mafia,” she says, adding, “I would never have known mobsters if it hadn’t been for Frank Sinatra.”
Is Frank Sinatra the key to it all? That’s what one woman in Newark, claiming to be psychic, writes to the FBI in March 1985. “Frank Sinatra is the main problem,” she declares. “He is responsible for the Kennedy curse: Joe, Jack, Bobby.”
The last line in Frank Sinatra’s FBI file reads, “Newark [FBI] considers the captioned matter closed,” but an explanation for the successive Kennedy tragedies remains very much an open matter.
The House of Kennedy Page 8