The Devil's Chessboard

by David Talbot

  Like Dulles, General Clay occupied positions in the top ranks of the American establishment. After serving as the U.S. military governor in postwar Germany, Clay had worked with Dulles in Cold War propaganda projects like the Crusade for Freedom, returning to Germany in 1961 as an adviser to President Kennedy during the Berlin Wall crisis. Clay dangerously escalated the crisis without the president’s authorization by threatening to knock down the recently erected wall with U.S. Army tanks. It took all of the Kennedy brothers’ back-channel diplomatic skills to defuse the confrontation at Checkpoint Charlie. A disgusted Clay later accused Kennedy of losing his “nerve.” By 1963, Clay had given up military service for a corporate career, taking a senior partner position with Lehman Brothers, the Wall Street investment firm, as well as board seats at General Motors and other major companies.

  Paulino Sierra Martinez was not the type of man with whom Dulles or Clay normally dined at the Army and Navy Club or the Metropolitan Club. The son of a Cuban police sergeant, Sierra had worked his way up in Havana society, landing a job in dictator Fulgencio Batista’s foreign ministry. But some of his intimates suspected that Sierra’s government post was a cover for his true profession, as a Batista assassin. Fleeing Castro’s Cuba, Sierra settled first in Miami, but after passing his U.S. bar exams, he went to work in the legal department of the Chicago-based Union Tank Car Company, a railroad freight company that had been built by the Rockefeller family. It was in Chicago that Sierra suddenly emerged as a mysterious player in the confusing and conflict-ridden Cuban exile movement.

  In May 1963, following his Washington meeting with Dulles and Clay, Sierra—who was virtually unknown in anti-Castro circles—convened a meeting of Cuban exile leaders at the Royalton Hotel in Miami. The leaders were skeptical about the tall, well-dressed man from Chicago, with the long, homely face that put some people in mind of Lincoln. But the anti-Castro movement was in disarray following Kennedy’s withdrawal of support, and Sierra arrived in Miami with an enticing proposal—and the promise of big money to go along with it.

  Sierra told the group that he represented an alliance of major U.S. corporations that wanted to regain their lost investments in Cuba. He did not name the companies, but on other occasions he dropped such Fortune 500 brand names as United Fruit, U.S. Steel, DuPont, and Standard Oil. Sierra claimed that these corporations were willing to put up as much as $30 million if the fractured anti-Castro movement could reassemble itself and mount an invasion of the island. He explained that such an operation would not have Washington’s official approval but would be supported by officers within the U.S. military, who would help provide weapons and training bases.

  Freely spreading money around, Sierra attracted enough support from within the anti-Castro network to form a coalition he ambitiously titled the Junta of the Government of Cuba in Exile. He crisscrossed the country, drumming up support for the new organization and going on a weapons-buying spree. The sources of Sierra’s funds, which were passed to him through Union Tank Car, remained something of a mystery, although an article in The Miami News indicated that at least some of his money was coming from organized crime lords who were intent on winning back their Havana gambling casinos and prostitution franchises, which before Castro had been a source of enormous underworld profits.

  Law enforcement agencies began tracking Sierra as he pursued his shady agenda, but in June the FBI terminated its investigation after concluding that he was involved in nothing more than a “con job.” The Chicago office of the Secret Service, however, suspected that Sierra was a more sinister figure. By November 1963, Chicago—like Miami, New Orleans, and Dallas—had become a nest of anti-Kennedy intrigue. On November 2, local Secret Service officials foiled a well-organized assassination plot against President Kennedy. After landing at Chicago’s O’Hare Airport that day, Kennedy was scheduled to ride in a motorcade to Soldier Field for the annual Army-Navy football game. But the motorcade was canceled after the Secret Service exposed a plot to ambush the president from a tall warehouse building as his limousine slowed for a hairpin turn. The plot, which involved a sniper team composed of a disgruntled ex-marine who worked in the building and at least two Cuban marksmen, bore a disturbing resemblance to the series of events that would claim Kennedy’s life twenty days later in Dallas.

  The Secret Service could not connect Sierra to the Chicago assassination plot, but his name did come up in relation to another troubling report. On November 21, the day before JFK’s assassination, a serious threat against the president was made by an outspoken anti-Kennedy Cuban exile leader named Homer Echevarria. While negotiating an illegal arms purchase, Echevarria reportedly said that he had “plenty of money” and would conclude the deal “as soon as we take care of Kennedy.” Sources told the Secret Service that the Echevarria weapons purchase was being financed by Sierra with mob money. After the president’s assassination, the Secret Service planned to pursue an investigation into Echevarria’s threat and the Sierra arms deal, but the agency’s probe was shut down by the FBI after President Johnson gave the bureau responsibility for the case.

  Following Kennedy’s death, Paulino Sierra Martinez faded from the front lines of the anti-Castro campaign. Accused by Union Tank Car’s legal counsel of wasting the Junta’s funds, he was eventually replaced as head of the organization. But according to relatives of Sierra, he continued to pursue his underground war against Castro and other left-wing leaders in Latin America. Tough-looking men carrying concealed rifles showed up from time to time at Sierra’s Chicago apartment—men whom one of his children described as “father’s banditos.” Sierra, who frequently packed his own gun, even when taking his young granddaughter to the zoo one day, continued to travel widely well into the 1970s, including to Chile, where he briefly relocated during the CIA-orchestrated unrest that led to the violent overthrow of President Salvador Allende in 1973.

  Although Sierra never discussed his hidden life with his son, Paul Sierra became convinced that his father was involved with U.S. intelligence. “I think that personally, Father’s patriotism and hatred for the Communists made him go a little overboard,” the younger man concluded.

  More than a dozen years after the Secret Service’s abortive effort to find out more about Paulino Sierra Martinez, the House Select Committee on Assassinations—which reopened the JFK case in the 1970s—again raised questions about Sierra. The sprawling congressional investigation ultimately concluded that Kennedy was the victim of a conspiracy, but it was unable to pin down the identities of those involved or the source of their funds. Committee investigators were intrigued by Sierra’s unsavory connections, including to three sketchy characters who showed up with Lee Harvey Oswald at the Dallas home of Silvia Odio, the daughter of a prominent anti-Castro activist, in September 1963. But, in the end, lacking the time and resources to fully pursue its leads, the congressional panel was forced to acknowledge that the “relevance to the assassination” of Sierra’s activities “remained undetermined.”

  At least the House Select Committee on Assassinations tried to shed some light on Sierra and his auspices. The first official inquest into President Kennedy’s assassination—conducted by the Warren Commission in 1964—made no serious effort to examine anti-Castro militants like Sierra and their connections to the CIA and organized crime. Despite the Secret Service’s suspicions about Sierra, his name appears nowhere in the Warren Report’s twenty-six volumes. Allen Dulles, a prominent member of the Warren Commission, could have revealed what he knew about Sierra. But Dulles never brought up Sierra’s name—nor did he ever inform fellow commission members that he had met with someone whom the Secret Service regarded as a person of interest in the Kennedy assassination.

  It remains one of the many enduring mysteries of the Kennedy case. Why did Dulles meet with Paulino Sierra Martinez in April 1963? What brought together the former CIA director and an obscure, Mafia-connected, anti-Castro conspirator with a penchant for violent action? As Dulles was keenly aware, organizing a paramilita
ry operation against the Cuban government was, by the spring of 1963, a violation of Kennedy administration policy and of federal law. By meeting with a character like Sierra, Dulles made it abundantly clear how little regard he had for the president’s authority—and perhaps for his life.

  17

  The Parting Glass

  In the summer of 1963, President Kennedy flew to Europe for what would be the final overseas trip of his life. Although he had left Washington, the forces of political tumult set loose by his presidency followed him abroad. These forces came swirling together in Rome during JFK’s official visit to the ancient imperial capital, where tour guides still pointed out the stone steps on which Julius Caesar’s blood was spilled.

  On the sultry evening of July 1, Kennedy was feted by Italian president Antonio Segni at the Quirinale Palace, the official residence of popes, kings, and chiefs of state since the sixteenth century. At the formal banquet—watched over by the extravagantly uniformed Corazzieri honor guard, in their torso-hugging white tunics and gold helmets with flowing horsetails—Segni paid tribute during his toast to Kennedy’s recent Peace Speech at American University. Kennedy’s “dynamic” quest for peace, declared Segni, was a welcome break from the “static” era of nuclear deadlock. After Segni concluded his welcoming remarks, JFK stood up and reiterated his peace message, telling the assembled dignitaries that “war is not inevitable, and that an effective end to the arms race would offer greater security than its indefinite continuation.” Invoking Italy’s volatile political history, Kennedy then warned of “the siren temptation of those with seemingly swift and easy answers on the far right and the far left.” It was up to those who advocated “social justice and progress and human rights,” said Kennedy, to make the more difficult ideals of democracy a reality for people all over the world.

  Kennedy’s Italian itinerary, which included an audience with the new pope, Paul VI, at the Vatican and a side trip to Naples, was the finale to a triumphant European tour that was highlighted by a sentimental stopover in Ireland and his resounding challenge to Soviet tyranny at the Berlin Wall (“Ich bin ein Berliner . . .”). The crowds in Rome that greeted Kennedy’s motorcade were comparatively sparse, as the presidential limousine and its police motorcycle squadron made the long and winding trip to the Quirinale along the boulevards and narrow streets of the capital. The Eternal City could be blasé about visiting dignitaries, and the summer heat was sweltering. Yet underneath the city’s unruffled exterior ran a shiver of excitement about the visiting American president who cut such a bella figura—particularly in contrast to Italy’s aging, white-haired leaders. Even L’Unità, the Italian Communist Party newspaper, appreciatively noted JFK’s tall, tan good looks and his stylish blue-gray suit and purple tie.

  But as the young American president was taking the spotlight at the Quirinale, the forces aligned against him were converging in Rome. Behind the elaborate festivities at the palace that night was an intense Italian political drama, one with international ramifications. Since the mid-1950s, Italy had been hotly debating l’apertura a sinistra—“the opening to the left”—a political deal that would peel away the Socialist Party from its traditional Communist Party allies and result in a left-center coalition with the ruling Christian Democrats. Pietro Nenni, the wily, seventy-two-year-old political survivor who headed the Socialist Party, had been diligently trying to maneuver his party away from its alliance with the Italian Communists ever since the Soviet invasion of Hungary in 1956. Nenni hoped that with a forward-looking new president in the White House, the United States—which had quietly dominated Italian politics since World War II—would finally give its blessing to the apertura.

  The Eisenhower administration had flatly opposed the opening to the left, seeing a Socialist partnership with the Christian Democrats as a slippery slope that would lead to a Communist-dominated government in Rome. Eisenhower officials worried that if the Socialists were allowed into Italy’s government, they would try to steer Rome on a neutral course between Washington and Moscow. The CIA—which had a proprietary sensibility about Italy, dating back to its well-funded, covert campaign to thwart a Communist Party victory in the country’s 1948 elections—engaged in its usual schemes, along with its allies in the Italian intelligence services, to block the apertura. The agency’s anti-left strategy in Italy was spearheaded by Jim Angleton who, with his deep personal roots in the country, had turned Rome into a key Cold War battleground. The Eisenhower administration’s resistance to the apertura was further enforced by Clare Booth Luce, Ike’s ambassador to Rome.

  It was Arthur Schlesinger who convinced President Kennedy to break with Eisenhower policy and support Italy’s opening to the left. “My impression is that [Nenni] has honestly broken with the Communists,” the White House aide informed Kennedy in a March 1962 memo. Schlesinger had his own sentimental attachment to Italy, dating back to his boyhood when his father offered sanctuary in Harvard’s history department to anti-Mussolini exile Gaetano Salvemini, an Italian Socialist politician and historian.

  Angleton was so furious about the new tilt in favor of Nenni’s Socialists that he began telling people that Schlesinger was a Soviet agent. Meanwhile, former ambassador Luce lobbied frantically against the apertura, dashing off a long, somewhat incoherent letter to JFK in February 1963, filled with random observations about the growing threat from the left in Rome. “Italy’s pro-West government has had one foot on the Moscow banana peel for seventeen years,” she observed. If the “pro-Communist Socialists” were brought into power, “the Italian Communist Party will negotiate Italy’s future with the U.S.S.R.” Luce concluded by warning the president not to fall into a left-wing trap during his visit to Rome. “In the present climate, there is a real possibility you may be very embarrassed by the enthusiastic reception you will get from the Communists! I can see the banners now: ‘Vivo [sic] Kennedy e Khrushchev!’”

  Frustrated by the stubborn bureaucratic resistance that Kennedy was receiving from within his own government to his shifting policy on Italy, Schlesinger sent the president an angry memo in January 1963. “Lest you think you run the U.S. government, the [Italy] matter is still under debate,” the White House aide acidly remarked.

  But President Kennedy eventually ignored the political pushback and embraced Italy’s apertura. He became so enamored of the idea of building a strong center-left coalition to anchor Italy’s turbulent politics that he arranged for United Auto Workers leaders Walter and Victor Reuther, to whom he had strong political ties, to help fund Nenni’s party. JFK’s trip to Rome gave him the opportunity to officially anoint the opening to the left.

  After dinner at the Quirinale, Kennedy used the rest of the evening to quietly communicate his views to the leading Italian political figures gathered at the event. As the president strolled along the gravel paths of the lush palace garden, he was approached by various politicians and officials, including Palmiro Togliatti, the head of Italy’s potent Communist Party, with whom he exchanged a few words. When an Italian news photographer snapped a shot of the two men in conversation, Kennedy later asked him for the film, concerned about the impact that the photo might have in Italy’s fraught political climate. Amazingly, the photographer obliged the American president.

  In a far corner of the garden, a low wooden platform bathed in spotlights had been set up for the president to hold private audiences with Italy’s dignitaries. The longest conversation that Kennedy held that evening was with the old Socialist warrior, Pietro Nenni. As the two men huddled together on the little stage, their faces nearly touching, they were a study in contrasts: Kennedy tall, youthful, and glamorous; Nenni, diminutive, bespectacled, and balding. But Nenni clearly felt he had found a political soul mate in Kennedy. The previous year, Nenni had tweaked the U.S. foreign policy establishment with an essay in Foreign Affairs, in which he defended his party’s neutralist stand in the Cold War and attacked Western imperialism, charging U.S. and European governments with backing “Fascist-type dictator
ships” in the Third World. “They have spent hundreds of millions of dollars in shoring up rotten situations doomed in any case to crumble,” wrote the Italian. “They have opened doors to Communists instead of supporting democratic and socialist forces that would be capable of directing the impulse to freedom of the colonial peoples.” Now, as a long line of other Italian politicians waited impatiently to speak with Kennedy, Nenni was engaged in rapt conversation with an American president who had voiced the same sentiments.

  When his audience with Kennedy finally came to an end, Nenni was “absolutely enraptured and happy as he could be,” according to a U.S. embassy official who was there. Stepping off the platform, the old man wrapped his arms around his wife and murmured something into her ear. As they walked away, Nenni wiped tears from his eyes. Later, Nenni’s wife told a group of American diplomats attending the Quirinale event that her husband had been “enchanted” by JFK. The Socialist leader was convinced that his political dream was about to come true: after years of determined U.S. resistance, Italy’s democratic left was at last to become part of the government.

  The president, too, thought his trip to Rome was a “considerable success,” telling Schlesinger on his return to Washington that he had a “good talk” with Nenni and adding, “So far as I could see, everyone in Italy is for an opening to the left.”

  But Allen Dulles and his old cohorts in the CIA’s Rome station did not share the president’s enthusiasm for the Italian political developments, and they boldly communicated their dissent to Christian Democratic officials. This is a remarkable and, until now, unreported story, one that sheds new light on the growing fissures in the Kennedy administration. Shortly after JFK flew home from Italy, Dino John Pionzio, the CIA’s leading operator in Italy at the time, huddled with Sereno Freato, the administrative secretary of Aldo Moro—a rising star in the Christian Democratic Party who would soon become Italy’s prime minister. Pionzio, a Skull and Bones member at Yale (Class of 1950) and zealous Cold Warrior, was adamantly opposed to the opening to the left. The CIA man wanted to know what Moro had discussed with Kennedy a few days earlier during an afternoon stroll that JFK and the Italian politician had taken through the Quirinale garden. To his great dismay, Pionzio was told that Moro and Kennedy had agreed the apertura should go forward.