I began work on the CIA’s Cuba desk in July 1964, up on the sixth floor of the Agency’s new headquarters building in Langley, Virginia. There were five or six of us working on Cuba, at a time when there were few other leaders of such intense interest in Washington policy circles as Fidel Castro.
New CIA analysts in the 1960s learned by the seat of their pants. There was no “CIA University,” with pretentious bureaucrats posing as deans or department chairs, and not much codified wisdom about analytic tradecraft. We probably learned better and faster than later generations did, but if so, it was because we were mentored by some of the best the Agency has ever produced.
My teachers were all from the founding generation of intelligence analysts. Most were wise and worn veterans of World War II, many of them scholars and old school intellectuals with broad ranges of interests. Among them were nationally recognized camellia and orchid experts, medievalists, linguists, anthropologists, former English professors, and cross-cultural psychologists. Many of them, even those who had no direct responsibility for Cuba or Latin America analysis, were keenly interested in Castro. They gave me good counsel.
“You’ve got to get into his shoes,” several urged me. They really meant Fidel’s trademark combat boots and khaki uniform. “You have to try to think like him, understand why he reacts as he does.” They told me to examine his cognitive style, his emotional underpinnings, psychological dynamics, and to discover whatever was behind the artifice of his performance style.
They told me to ponder the way he makes decisions and goes about problem solving. What motivates and disturbs him? How did all of his experiences before winning power influence his outlook and personality? Unfortunately, very little of his biography was known at that time, as he did his best to obfuscate his formative years and live down his gangland past and penchant for violence.
Almost nothing about his painful, dichotomized childhood was known outside of Cuba, and there was little reliable information about his intellectual formation. Assessing his personality was a high priority precisely because he was so difficult to understand. There was a need to get under his carapace, to probe and understand his inner workings.
Remote leadership assessment enjoyed considerable legitimacy in the CIA in those days, much more so than in recent years. Nationally respected political psychologists and psychiatrists were on staff, and their work was highly valued. It was a positive legacy carried over into the Agency by veterans of the wartime Office of Strategic Services, the OSS, CIA’s parent organization.
During World War II the OSS commissioned a classic psychiatric study, the first of its type ever done inside the U. S. government. A team of four distinguished professors and psychologists completed a book-length psychological analysis of Adolf Hitler. It was classified Secret, although a review of an unexpurgated copy today finds no apparent use of sensitive information.
A landmark work, it brilliantly probed Hitler’s character and personality, preparing the ground for many similar studies of other foreign leaders. It was a particularly appropriate model for a young Cuba and Castro analyst. That was not because I or any of my mentors compared Castro with Hitler or rejected his revolution out of hand. There was actually a lot of sympathy for what he was trying to do in Cuba, and we appreciated that he was one of a kind.
Except for the Soviet Union, there may not have been any intelligence targets of so much concern in Washington. McGeorge Bundy, President Kennedy’s National Security Adviser, is said to have kept three boxes for incoming mail on his desk at the White House. There was an In box, an Out box, and a Cuba box.
Fidel was an obsession for that administration. The Bay of Pigs fiasco in April 1961 and a number of CIA-orchestrated assassination plots against Fidel and his mysterious brother Raul were followed by the covert Operation MONGOOSE that unleashed terrorist-type raids and sabotage attacks on the island. Cuba’s strategic alliance with the Soviet Union had been solidified by the time I joined the Cuba desk. Every property on the island owned by American citizens or companies had been nationalized. The list of grievances on both sides of the Florida Straits was long and ugly.
The October 1962 missile crisis was the only time the world’s two superpowers went to the brink of nuclear conflagration, all because of the strategic importance of the Castros’ Cuba. American officials at that time mistakenly considered Fidel merely a pawn of the Soviet Union, and his brother Raul, the defense minister, to be Fidel’s obsequious minion. By the time I got involved in Cuba analysis, the first of those assumptions had been discarded although the second endured for many more years.
The Castro regime posed many types of challenges to the United States in the 1960s. Brutal dictatorships and flagship democracies alike were targets of Cuban subversion. Fidel’s speeches were broadcast by powerful Radio Havana antennas and were easily heard through much of Latin America. He had a huge, sympathetic following in the region. Young people, nationalists, intellectuals, and others in large numbers were converted by his revolutionary incantations and, with Cuban government encouragement and support, guerrilla groups took to the hills in several countries.
American intelligence concluded that some of them would probably succeed. A national intelligence estimate—the highest level of finished intelligence analysis—concluded in June 1960 that the chances were “appreciable that one or more Castro-like regimes” would seize power.1 Through most of the decade of the 1960s, and again during the 1980s, fear that sibling revolutionary regimes would be lifted into power with Cuban assistance was a central preoccupation of American policymakers.
Working the Cuba beat as a CIA political and leadership analyst was an exciting challenge. It was a hot, front burner issue, guaranteeing that the conclusions I wrote up for Top Secret intelligence assessments would reach readers at the highest levels of government.
Latin America had been my core interest since graduate school. I had lived and studied in Spain and Mexico but had no interest in a career in overseas espionage. Analysts and operatives in the CIA have always been distant relatives. Analysis is sedentary, mostly anonymous, often tedious work, and even in the 1960s, before there was any structured congressional oversight of intelligence, there were risks in getting it wrong. Nearly all the examples of notorious intelligence failures have been errors of analysis.
Nonetheless, there was nothing I wanted to do more than to examine the entrails of the Cuban revolution as a CIA analyst. What that really meant was that I was dedicating myself to becoming a Fidel Castro specialist. He was one of the most complex, dynamic, yet inexplicable leaders of the twentieth century.
Raul, younger by five years and slated to succeed him since the earliest days of their regime, gradually rose in my thinking as an essential key to understanding Fidel. By the 1970s I had concluded that Raul was underestimated by nearly all foreign observers, an easy oversight considering his brother’s titanic personality and charisma. I realized that Raul was his brother’s one truly indispensable ally and that his brilliant, steady leadership of the Cuban armed forces secured the revolution. Without him it is unlikely Fidel would still be in power.
The truth, I learned, was that each of the two was his brother’s keeper. Their talents, styles, and proclivities intersect and complement each other. Raul’s greatest leadership strengths are Fidel’s most notable weaknesses. Where Raul is deficient—in communication skills, strategic planning, and crisis management—Fidel is a grandmaster. Since the mid-1950s they have worked together hand in glove, with only a few known aggravations.
I recently discussed the brothers’ relationship with an astute former Cuban intelligence officer, now living in Miami, who knew them both. He said that if the Cuban Revolution can be considered an ongoing drama, then Fidel must be thought of as its director and Raul its producer. Fidel is the visionary. He has been the creative genius of its many acts and scenes for more than four and a half decades. But almost none of them would have been possible without Raul’s organizational skills.
Today, as the aging and infirm Fidel is nearing the end of his reign, Raul is assuming a larger decision-making role and waiting in the wings to assume power in his own right. What kind of leader will he be? Will he want to improve relations with the United States? If so, he will have little experience to guide him. He has spent a total of only about twenty-four hours in the United States, many years ago, and since then has expressed almost no interest in developing contacts with Americans or trying better to understand his neighbor.
Raul has frequently been described as “enigmatic.” My hope is that he will emerge in ensuing chapters as a leader at least as fascinating as his better-known brother.