The Devil's Chessboard

by David Talbot

  America could not continue to inspire the world, Kennedy went on, unless it “practiced what it preaches” at home. “If a Negro baby is born here and a white baby is born next door, the Negro baby’s chance of finishing high school is about 60 percent of the white baby. This baby’s chance of getting through college is about a third of that baby’s. His chance of being unemployed is four times that baby’s.” All that must change, JFK told the audience. “White people are a minority in the world,” he said. They could no longer hold back the dreams of the rest of the world. Kennedy vowed that if he were elected, he would align America with the winds of change. “I believe it is important that the president of the United States personify the ideals of our society, speak out on this, associate ourselves with the great fight for equality.”

  In the next three years, as Cuba became the flaming focal point of U.S. foreign policy, Kennedy would continue to wrestle with his relationship to Castro and the revolutionary change that he represented. As president, JFK’s posture on Cuba gradually softened, with the White House inching awkwardly toward a state of peaceful coexistence with the neighbor whom Kennedy once called “dangerous.” The fitful process of rapprochement with Cuba would set off a turbulent reaction in Washington, particularly within the national security circles still dominated by Dulles hard-liners. In these men’s minds, it was not just Havana that loomed as a hotbed of dangerous ideas, it was the Kennedy White House.

  14

  The Torch Is Passed

  The cruel circus of American politics has a way of exposing a candidate’s inner self, particularly the hurly-burly of congressional campaigns, where the battle is fought up close and on one’s home turf. Allen Dulles briefly threw himself into the political arena in August 1938, when he declared himself a candidate in the Republican primary for the Sixteenth Congressional District, on Manhattan’s Upper East Side, where he and Clover maintained a town house. Like Foster, who later ran a similarly ill-fated campaign for the U.S. Senate, Allen had a nuanced feel for power but not for politics. The brothers were imbued with a sense of public service, but in their minds, democracy was something to be saved from the demos. “Democracy works only if the so-called intelligent people make it work,” Allen told the press on the eve of his campaign. “You can’t sit back and let democracy run itself.”

  Dulles’s patrician sensibility did not play well in the campaign, even with the posh Republican voters on the Upper East Side. During the race, he put together all of the right elements, like a corporate lawyer meticulously building his case. He lined up the support of prestigious Republicans, such as Elihu Root Jr., the son of Teddy Roosevelt’s secretary of state, who served as his honorary campaign chairman. He secured the endorsements of the leading New York newspapers, including the Times and the Herald Tribune. And he opened up a campaign office at the Belmont Plaza Hotel, where Clover dutifully wrote several hundred letters soliciting support from women voters in the district, like a Junior League doyenne volunteering for a favorite charity. But there was no passion in the Dulles campaign. His speeches were stilted and his debate performance was lawyerly and bloodless.

  The monthlong primary campaign pitted Dulles against the incumbent, a conservative Democratic congressman named John J. O’Connor, who had cross-filed in the Republican primary after President Roosevelt announced his intention to purge O’Connor as a traitor to the New Deal. During the brief race, Dulles tried to carefully parse his attacks on the popular president, expressing sympathy with FDR’s “broad social aims” while denouncing his “dictatorial attitude.” But O’Connor—who had established himself as one of the more effective opponents of the New Deal in Congress—came across as a more muscular enemy of Roosevelt. And when the battle-scarred political warhorse turned his invective on Dulles, accusing him of “selling out” his country to “international interests” and Wall Street titans like J. Pierpont Morgan, Dulles could only muster a rational-sounding, but feeble, reply.

  On Election Day, September 21, Dulles went down to a thumping defeat, losing the Republican nomination by a three-to-two margin to a man who did not even belong to the party. Dulles promptly returned to the world of discreet power that he knew best, never again subjecting himself to the slings and arrows of electoral combat.

  On the surface, John F. Kennedy seemed similarly unsuited for the rough-and-tumble of democracy. Privileged, reserved, and physically frail, young Jack Kennedy was a far cry from his glad-handing political forebears, such as his maternal grandfather, John “Honey Fitz” Fitzgerald, the perennial Boston politician who wooed voters with his gift for song and blarney. Late into his career, JFK continued to worry that he was too introverted for politics. In January 1960, three days after declaring his presidential candidacy, Kennedy confided to friends over dinner, “I’m not a political type.” In contrast to his grandfather, who “wanted to talk to everybody,” added Kennedy, “I’d rather read a book on a plane than talk to the fellow next to me.”

  When he made his political debut in 1946, running for Congress from the Boston-Cambridge Eleventh District, the twenty-eight-year-old Kennedy was far from a shoo-in, despite his father’s wealth and connections. The sprawling district encompassed a slew of tough Irish and Italian working-class neighborhoods and slums, and the Choate- and Harvard-educated candidate seemed too aloof a character to outrun the crowded pack of experienced political pros that he faced in the Democratic primary. Joe Kennedy tried to outfit his son with the best campaign brain trust that money could buy, but JFK preferred to work with young war veterans like himself. Jack Kennedy sought out Dave Powers, an Air Force veteran who had grown up in scruffy, Irish-Catholic Charlestown and was a local political wise guy. The son of a dockworker who had died when Powers was two, leaving his widow with eight children to raise, the political operator knew the dreams and heartaches of the families crowded into the neighborhood’s “three-decker” tenements. Powers ushered five masses every Sunday at St. Catherine’s Church and played second base on the parish baseball team. “I knew just about everybody in Charlestown.”

  When Kennedy first approached him in a Charlestown tavern to ask him to join his campaign, Powers turned him down flat. A millionaire’s son running for Congress in a shot-and-beer district? He didn’t stand a chance. Kennedy didn’t seem cut out for Boston’s brawling politics. In fact, the young man—who would soon be diagnosed with Addison’s disease and told that he would not live past forty-five—did not seem long for this world. As the 1946 campaign got under way, Kennedy was plagued by severe back and abdominal distress that he had suffered ever since he was a teenager and had been aggravated during his war service in the South Pacific, where he had also picked up a case of malaria. He was painfully thin and his skin had an unhealthy, yellow tinge—whether from the atabrine he took for his malaria or from his Addison’s, it was unclear.

  Kennedy’s shy manner and boyish good looks made him seem more a poet than a politician to Powers, but he soon discovered that JFK was “aggressively shy.” Even after Powers turned him down over drinks at the bar, Kennedy kept dogging him, showing up a few nights later at his family’s three-decker flat and peppering him with questions. Well, if YOU were running in the district, what would YOU do? “He was very inquisitive. He could pick your mind.”

  A few days later, when Kennedy invited him to come to his first campaign appearance, Dave Powers gave in to his political destiny. JFK was addressing a group of Gold Star mothers—women who had lost sons during the war—at the Charlestown American Legion Hall. As Kennedy began to speak, a polite hush fell over the crowd. Powers stood listening in the back of the room, and at first the political operator—who was used to the stem-winding oratory of Boston legends like James Michael Curley—cringed at what he was hearing. The young candidate was painfully nervous, stuttering and visibly struggling for a way to connect with his audience. And then, it happened. Kennedy—whose own family had lost its firstborn son, Joseph Patrick Kennedy Jr., in the final days of the war—found his voice. “
I was getting sort of nervous,” recalled Powers years later, “and then [Jack] looked out at all these wonderful ladies and said, ‘I think I know how you feel, because my mother is a Gold Star mother too.’ And all the years I’ve been in politics, smoke-filled rooms and from Maine to Anchorage, Alaska, this reaction was unbelievable. He immediately was surrounded by all these Charlestown mothers and in the background I can hear them saying he reminds me of my own John or Joe or Pat, a loved one they had lost. Even I was overwhelmed.”

  After the event, as they walked back to Kennedy’s hotel suite, in an old political hangout on Beacon Street, the young candidate asked Powers how he had done. “It was great,” said Powers.

  “And then he reached out his hand and said, ‘Then will you be with me?’ And I shook his hand and I was with him from that day to Dallas.’”

  Kennedy went on to win the Democratic primary and the general election by landslides. He spent the rest of his life in politics, a profession he regarded as honorable and at which he displayed a unique talent, even if he never felt entirely comfortable with its showmanship. As he prepared to run for president, he expressed hope that the country was ready for a new style of politics. Perhaps you didn’t have to be a backslapping “happy warrior” like Hubert Humphrey, a leading rival for the 1960 Democratic nomination. “I just don’t think you have to have that type of personality to be successful today in politics,” JFK told friends, a bit wishfully, early in his campaign. “I think you have to be able to communicate a sense of conviction and intelligence and rather, some integrity. . . . Those three qualities are really it.”

  Every great life in politics has a theme: with John Kennedy, it was his horror of war and the endless suffering it brings. He felt it in a way that most politicians, blithely untouched by the savagery and idiocy of war, never feel it. “All war is stupid,” Kennedy had written home as a naval lieutenant in the South Pacific, where he had nearly lost his own life when his PT boat was carved in two by a Japanese destroyer. The death of his older brother only confirmed his deep disgust with war. “He was very close to my brother Joe, and it was a devastating loss to him personally,” recalled Senator Edward M. Kennedy, JFK’s youngest brother, near the end of his life. “He was a very different person when he came back from the war. I think this burned inside of him.”

  Allen Dulles had also felt the personal impact of war, when his son and namesake returned from Korea irreparably damaged. But his own family tragedy provoked no deep agonizing within Dulles about war or his central role in Washington’s machinery of violence. The spymaster liked to talk, in a way that sounded almost boastful, about his ability to dispatch men—including his own loyal agents—to their deaths. In contrast, during his years in the White House, Kennedy continually wrestled with ways to avoid bloodshed, again and again deflecting belligerent counsel from his national security advisers. Dulles came to see this as weakness, while Kennedy would conclude that his CIA director was a man of the past, recklessly provoking Cold War confrontations when the world was crying out for a new vision. Though it was largely hidden from the public, the duel between Kennedy and Dulles would define Washington’s “deep politics” in the early 1960s.

  Dulles first met Kennedy in winter 1954, while JFK was at his family’s Palm Beach mansion recovering from another agonizing round of back surgery. The freshman senator from Massachusetts, who had not yet made much of a political mark, did not strike the graying Washington power fixture as the sort of man with whom he would one day cross swords. Kennedy was so enfeebled from his latest surgical ordeal—which had put him in a coma, prompting a priest to administer the last rites—that he could barely hobble a few steps. He lay in bed most days, with nurses helping to turn him, reading, and taking notes for an article that would grow into his bestselling book, Profiles in Courage.

  From an early age, Kennedy’s afflictions had given him an acute sense of his fragile mortality. “At least one half of the days that he spent on this earth,” his brother Robert later observed, “were days of intense physical pain.” As president, JFK came to represent the very picture of youthful vigor and political revitalization. But in private, particularly during periods of extreme physical distress, Kennedy seemed to belong as much to the afterlife as to the living. In October 1953, while relaxing on Cape Cod after their wedding, Kennedy recited his favorite poem to his new wife, Jacqueline, “I Have a Rendezvous with Death.” Written by a young American poet named Alan Seeger—the uncle of folk singer Pete Seeger—before he died in battle in World War I, the poem spoke to the shadows in Kennedy’s soul, even in the bloom of marriage to a beautiful and vivacious young woman:

  God knows ’twere better to be deep

  Pillowed in silk and scented down,

  Where love throbs out in blissful sleep,

  Pulse nigh to pulse, and breath to breath,

  Where hushed awakenings are dear . . .

  But I’ve a rendezvous with Death

  At midnight in some flaming town,

  When Spring trips north again this year,

  And I to my pledged word am true,

  I shall not fail that rendezvous.

  Dulles was a frequent houseguest of the Kennedys’ Palm Beach neighbors, Charles and Jayne Wrightsman. Charlie Wrightsman was a globe-trotting oil millionaire who had met his much younger wife when he was pushing fifty and she was a twenty-four-year-old department store swimsuit model. Under his bullying tutelage, Jayne Wrightsman grew into a world-renowned art collector and high society hostess who would mentor Jacqueline Kennedy during the First Lady’s elaborate restoration of the White House.

  Charlie Wrightsman was a blunt-spoken former oil wildcatter whose ruggedly Republican values were right out of the pages of Ayn Rand. Wrightsman and Dulles, who served as the oilman’s attorney when he worked at Sullivan and Cromwell, forged a tight, mutually beneficial friendship. Wrightsman generously shared his lavish lifestyle with the less affluent Dulles, inviting the intelligence chief for frequent winter retreats at his Spanish-style estate in Palm Beach, with its Renoirs and Vermeers and its parquet floors acquired from the Palais Royal in Paris. The oil baron also sometimes enticed Dulles to join his wife and him on their yachting expeditions in the Mediterranean as well as their aviation adventures in their Learstar jet. “Jayne and I are leaving Paris on Thursday August 20 for Stavanger, Norway and points North,” Wrightsman wrote Dulles in July 1953 from the Hotel du Cap d’Antibes. “If you will join us, I will promise not to mention during our entire cruise that Senator McCarthy might be the next President of the United States.”

  Dulles, in turn, opened doors for Wrightsman in far-flung oil capitals like Baghdad and Tripoli, providing him with introductions to ambassadors, government ministers, and sheikhs. The oilman made sure to keep the spy chief in the loop, reporting back to him on the political intrigues in Europe and the Middle East.

  Clover resented the way that her husband slid so easily into the lap of luxury provided by millionaires like Wrightsman. Spending time in this gilded atmosphere brought out all of Clover’s mixed feelings about the world of privilege, a world where Allen served but did not fully belong.

  “The mere mention of the Wrightsmans,” recalled Mary Bancroft near the end of her life, “was apt to set off one of those fights [between Dulles and his wife] when they went at each other like a pair of fighting eagles—with Clover always being defeated by Allen’s stronger claws, until she retreated from the fray with feathers awry and deep wounds from those claws. It was terrible to witness how they fought.”

  Clover blamed the Wrightsmans for bringing out her husband’s “more reprehensible characteristics,” Bancroft observed, “namely . . . that he liked good food, good wine, and the chance to swim in a heated pool and afterwards to dry himself with a large, soft, expensive towel that had been warmed ahead of time ‘so you won’t get a shock.’ Clover liked luxury herself, but she certainly fought this ‘weakness’ tooth and nail and was always forcing herself to do uncomfortable and unpleasant
things that she thought ‘good for the soul,’ like the most rigid of the Puritan fathers.”

  It was the Wrightsmans who introduced the Dulleses to young Jack Kennedy. Charlie Wrightsman was no fan of the New Dealer Joe Kennedy, but he and his wife found themselves charmed by Jack and Jackie, who seemed to have the air of American royalty. Years later, after JFK was dead, Dulles recalled the day in early 1954 that he met the young senator. Invited by Joe Kennedy to drop by the family’s Palm Beach home while he was staying with the Wrightsmans, Dulles first came upon JFK as he was flat on his back. “He was suffering a good deal of pain, and he was lying on the sofa there in the study in Joe Kennedy’s house,” Dulles remembered, “and that was the first time that I saw him.” As the two men discussed various international hot spots, JFK would get up from time to time, wincing with pain, and gingerly walk a few paces before returning to the sofa. “He obviously wanted to learn,” said Dulles.

  On another occasion, JFK was invited to dinner at the Wrightsmans’ when both Dulles brothers were in attendance. “Jack Kennedy was quite a modest man in those days,” recalled the CIA chief. “I remember my brother was there [and] I don’t say [Kennedy] was overawed, but he was very respectful.”

  Thus began a relationship that Dulles regarded as tutorial—the education of a promising young man who had the proper regard for his elders. “He was always trying to get information—I don’t mean secrets or things of that kind, particularly, but to get himself informed. He wanted to get my views, and when my brother was there, his views on what we thought about things, and we had many, many talks together.” This, in Dulles’s mind, was the proper order of things—Kennedy as prince and acolyte and the Dulles brothers as court regents.