“[CUBA BECAME] A RED AIRCRAFT CARRIER ONLY NINETY MILES OFF THE COAST OF FLORIDA.”

—NATHANIEL WEYL, RED STAR OVER CUBA, 1960

Early in 1960, after the United States cut off all imports of Cuban sugar, Cuba reacted by nationalizing all American businesses and commercial property. This provoked Eisenhower to announce that military action against Cuba was imminent. He would not “tolerate the establishment of a regime dominated by international communism in the Western Hemisphere,” the president said.1 The Soviets responded by announcing that they would buy all the sugar that had been allotted for the American market. Premier Nikita Khrushchev vowed that the Soviet Union would protect Cuba from any invasion, and Cuban foreign minister Raúl Roa declared before the United Nations assembly that his small country “could have no other course than to accept this assistance with gratitude.”² The events that would lead to the Bay of Pigs invasion and the missile crisis were set in motion.

On a fine St. Patrick's Day in 1960, the red phone in the CIA director's office rang. It was President Eisenhower authorizing the Agency to engage in covert actions against the Castro regime, the so-called Cuba Project.³ Allen Dulles was now set to implement his plan to terrorize the Cuban populace. Once again, the US State Department invoked the Monroe Doctrine of 1823 in order to intervene in Latin American affairs.

In 1954, famed aviator Jimmy Doolittle, who led a bombing raid on Tokyo during World War II (Twenty Seconds over Tokyo is the movie), was commissioned by Eisenhower to determine the CIA's capability in responding to the new threats created by the Cold War. On the Doolittle Commission sat the aviator himself and William Pawley.

Doolittle and Pawley, who had President Eisenhower's ear through his long public service, issued the report asserting that the United States had to abandon its concept of fair play “in the face of [an] implacable enemy and subvert, sabotage, and destroy enemies with more clever and sophisticated means.”4 If this sounds like automatic warfare, perhaps it was the intent.

Dulles was more than ready. On May 14, 1959, shortly after the Castro-Nixon verbal slugfest, an attorney named Alex E. Carlson filed corporate papers with the Dade County Clerk for a Double-Chek Corporation, whose business was stated as “brokerage.” The company address was close to the Miami International Airport, and most of its clients were tramp airlines.

Dulles could now tap into the director's contingency fund to finance the operation—not that the tweedy, pipe-smoking Boston Brahmin's family didn't own large blocks of United Fruit stock.⁵ The operation was nameless, but insiders called it the Dulles Bomber Wing. Double-Chek was a CIA front that would be subject to the Neutrality Act when it was enacted in late October 1962. It recruited ex-military pilots for missions over Cuba, strafing trains, firebombing cane fields, and hitting oil tanks, commercial buildings, and other targets designed to demoralize the population, commonly known as terrorism, to soften up the home front in preparation for a takeover by US Marines stationed at Guantanamo and the Panama Canal Zone.⁶ Anyone curious enough to inquire about the strange company was given a flippant answer like, “We fly chickens to the Dominican Republic” or “We broker for Czech clients.”⁷ As it turned out, the CIA estimate of Castro's domestic support was significantly short.

So the Cuba Project was finally underway, with Nixon as its action officer, even though it was unauthorized until April 17, 1960, when Ike approved the covert operation. It is probable that Dulles ratcheted up a schedule of operations to please Eisenhower's wish that Fidel be overthrown before the end of his term.

Castro's air force consisted of leftovers from the Batista force, which would pose no threat to the CIA's fleet of B-26 light bombers refitted from World War II, which were so common on the surplus market that they were difficult to trace. The registration numbers were painted out, and their bases were remote strips in Florida and Guatemala. The CIA fleet also had a few sleek P-51 Mustangs. All pilots were screened by Double-Chek.

To defend the homeland against these attacks, which showed no sign of abating, Cuba needed its own warplanes. Dulles learned that Castro had turned to Great Britain, which had sold seventeen Sea Furys to Batista that would even the score when delivered to Cuba. Castro changed the order to Hawker Siddeley jets that would give him the advantage. Britain apparently looked dimly on the aggressive feelings that the United States exhibited toward Cuba, and there was every indication that the deal would go through.

On December 2, 1959, the House of Lords debated the matter, then turned down the sale on the grounds that the military aircraft would introduce a new factor into a very delicate situation. Although the Americans cherished the thought that Dulles had put pressure on through his Old Boy network, Foreign Office records8 declassified on March 22, 2001, reveal that a week before the House of Lords debate, Allen Dulles, who had connections deep inside the British intelligence services, let it be known to the British Embassy in Washington that his country looked with disfavor on the sale of aircraft to Cuba. The island was now unable to guard its airspace.

Allen Dulles's plan was to have the Soviets supply planes to Cuba by default. This would provide justification on the world stage for the US invocation of the Monroe Doctrine. Paradoxically, Dulles was in no small measure responsible for Cuba becoming, in the metaphor of its shriller detractors, “a Red aircraft carrier only ninety miles off the coast of Florida.”⁹

On October 24, 1959, the B-26 sent to shower the American Society of Travel Agents in the Havana Hilton hotel with leaflets branding Castro a “communist tool,” banked north and disappeared. Since the B-26 headed north, there was suspicion that it came from Florida. The United States Department of State declared it knew nothing about the mystery craft, and a check of registrations did not show a Frank Fiorini. State apparently was aware that Fiorini was Frank Sturgis, the man of many faces, including that of CIA operative. At the time he was flying “study flights” under the direction of Juaquin San Jenis, a ranking Agency officer who functioned under the cover of a Miami car dealership, upon being called and given the coordinates to slip through a gap in the picket line of US surveillance aircraft and penetrate Cuban airspace.10 This would activate Cuban electronic defenses that would be picked up and analyzed by the spy ship Pocono in the Straits of Florida. In our 1974 interview, Frank said that he was paid by checks drawn on a food-products company and a department store. He had no contact with either.

Since it was a rump operation outside the Cuba Project, Dulles's Bomber Wing was able to hire pilots flying for anti-Castro action groups that proliferated in Florida. One particularly notorious example was the Insurrectional Movement for the Recovery of the Revolution (MIRR), which received CIA subsidies¹¹ but never yielded any degree of control over its activities. The maniacal head of MIRR was a pediatrician named Orlando Bosch, who once ran a coast-to-coast bombing conspiracy known as Cuban Power. The good doctor almost succeeded in knocking off Henry Kissinger in Costa Rica. But it was his role in the 1976 midair bombing of a Cuban airliner over the Caribbean that cost seventy-nine lives that brought him lasting notoriety. Despite this violent record, Bosch was lionized by the Bush family. Jeb Bush went so far as to use his influence to allow Bosch back into the United States.¹²

One of CIA-supported pilots was E. Carl McNabb, a United States Air Force (USAF) veteran who was a ringer for Paul Newman. I interviewed McNabb numerous times over a period of years. He told me that one night in Little Havana he was escorted to the headquarters of the Movimiento de Recuperación Revolucionaria (MRR)—in English, Movement to Recover the Revolution—an action group formed originally in Cuba by Manuel Artime. It was an unpretentious shingled house where an Anglo man was in a huddle with several Cubans. McNabb's escort turned him over to the Anglo man, who got right to the point. His name was Alex Carlson, and he represented Double-Chek Corporation at the Miami International Airport. They were becoming operational due to the serious threat Cuba posed to American soil. They were countering this threat. Did Carl ever fly B-26s? Was he checked out on them? No, Carl replied, but he was checked out on P-51s and could maybe borrow one. McNabb asked if Carlson was looking for unpaid volunteers as well. No, Alex replied, the pay for pilots was $10,000 per month, and the company prefers orphans. It was a low blow, but McNabb was aware of the CIA's propensity for hiring those without family. The CIA knew that if someone was killed or missing in action, it was much easier when he or she didn't have relatives who might become a nuisance.

It is worth noting that this convenient practice would come home to haunt Carlson. He procured five Alabama Air National Guard pilots because of their experience in B-26s, which were favored by the Alabama National Guard. When the current operation was halted because it was being merged into the Bay of Pigs invasion, Carlson recruited the same five pilots. They cartwheeled into the sea after being shot down by Castro's defenders. It was left to the unfortunate Alex Carlson to inform the widows that their husbands had disappeared on a C-54 cargo flight to Central America. It was of course a lie.13

For the MRR, McNabb was based on a coffee plantation in Guatemala, flying a P-51 Mustang whose cannon was mounted in the spinner. The craft was supposed to be “borrowed” from Carlos Prío's fleet of seven. The most intriguing mission he flew was flying cover for a B-26 on a firebombing raid on a cane field in western Cuba. While en route, his radio cut in that they were to switch to a high-value target who was scheduled to attend a baseball game that night. Who could it be besides Fidel himself? Assassination was not in McNabb's contract. Feigning engine trouble, he returned to base. From that day on, he was under suspicion.

Frank Sturgis almost blew McNabb's clandestine work for the MRR when he heard of planes making bombing and strafing runs at targets in Cuba from bases in Central America. The man of many trades couldn't resist getting back into action. He told Michael Canfield and A. J. Weberman in Coup d'Etat in America that he made an appointment to see President Miguel Ydigoras Fuentes of Guatemala with his sidekick, Diaz Lanz, “to arrange for bases there.”14 Ydigoras had restored authoritarian rule to the country after William Pawley engineered a 1956 overthrow. “So there were big headlines in the newspapers,” Sturgis said, “all over Latin America, and on television and radio, that I was there trying to set up bases to invade Cuba, which really came about a year later.”¹⁵ So naturally the president was embarrassed, and Sturgis was hassled by State when he got back to Florida. The bases remained secret, but it had been a close shave. McNabb was subsequently transferred to an African “liberation” movement but “got sick of shooting up boats carrying nuns on Lake Tanganyika and quit.”¹⁶

With the terror raids of the Dulles Bomber Wing—one explosive even hit a department store—the stage was set for the grand finale, the landing of the Marines in Cuba “from the Halls of Montezuma to the Shores of Tripoli.”¹⁷ Pawley had been there, done that, before. Cofounding the Flying Tigers was a stroke of genius. His success in business made him a powerful negotiator. It also enabled business connections with the Caribbean region's dictators, among them Batista, Trujillo of the Dominican Republic, and Samoza of Nicaragua. He socialized with them all, ordering the nation's favorite drink, Havana Club Rum. He became a diplomat sans portfolio, interacting with the dictators on the political level, and with Richard Nixon on the social level.

Pawley's diplomatic credentials were impressive. In 1950, President Harry S. Truman sent him on a mission to Madrid to negotiate with the Spanish dictator Francisco Franco on the construction of strategic air bases. Truman named him ambassador to Brazil and Peru. He became a confidant of Ike, who viewed him as a master of intrigue. It was with this set of credentials that Pawley became the point man in the campaign to bring about regime change in Cuba. Of course he had a financial stake in the outcome, but, absent that, he would still have pulled out all the stops. After all, he ranked second on Henry Kissinger's list of Fidel haters.¹⁸ As with most White House officials, the ambassador thought Castro would be an easy mark.

Bill Pawley was a top planner of the Guatemala-invasion comic opera, with the plot centering upon the National Palace. It was hardly an invasion model, yet Pawley put great stock in it. Perhaps this is because all involved treated it with gravitas rather than as the farce that it was. Pawley commented that on the eve of the invasion, Ike summoned Allen Dulles and his brother, Secretary of State John Foster Dulles, and, clearly uneasy, told them that they had to succeed or else.19 Years later, when the Bay of Pigs invasion of Cuba was being organized, there was an air of surety about the whole thing. Ike's only concern about Cuba, as expressed to Pawley, was to get it over and done with before he left office the following January.

In Guatemala, Jacobo Árbenz Guzmán had triggered a violent reaction by committing a personal agrarian reform and giving away some of his large land holdings. It was meant to be a humanitarian gesture, but to Pawley and Allen Dulles, who was on the board of United Fruit, it was ominous.²⁰ As Allen Dulles and Bill Pawley saw it, Guatemala had gone one more rung up the socialist ladder.²¹

The trouble was that the Army of Liberation assembled by the CIA, which was supposed to march into Guatemala City and take over, fled in dismay. It was left to the CIA's mercenary pilots to regain the initiative. Flying in relays, they bombed and strafed the city. At the same time, black-propaganda specialist David Atlee Phillips filled the airwaves with messages that rebels were closing in. After nine days, Árbenz lost his grip and capitulated. John Foster Dulles hailed the outcome as “a new and glorious chapter in the already great tradition of the American states.”²² But for the Guatemalan people, years of social progress went down the drain. American gamblers moved in, bribed the president's men, and opened casinos. United Fruit resumed business as usual. And Guatemala was lost for decades to right-wing militarists who failed to lift the country out of abject poverty but held power through death-squad atrocities against the opposition.

The Doolittle Report²³ left little to the imagination and provided a wide-open “pretext noir” for intervention in Cuba. When Castro dared to expropriate a large amount of United Fruit acreage in Cuba, retaliation was swift. Napalm bombs were dropped on cane fields and oil refineries.²⁴

In late 1959, the CIA, still not sure, decided to try to resolve whether Castro was at heart a Caribbean capitalist or a socialist drifter. To carry out the venture, it chose Jacob M. “Jack” Kaplan, proprietor of the Southwestern Sugar & Molasses Company, which had operations in the Caribbean, including Cuba. Kaplan's public image was that of a generous philanthropist in support of Brandeis University and the New School for Social Research, and prominent liberal politicians such as Hubert Humphrey and Chester Bowles. Behind the scenes, Kaplan was allowing his tax-free Kaplan Fund to be used by the CIA as a conduit for subsidizing left-of-center but anti-communist regimes and organizations25 in the Caribbean region as a firewall against communism, the prevailing policy at the time. By the time Castro came to power, however, Kaplan was in deep trouble. The IRS and the Patman Committee in Congress were probing his use of the Kaplan Fund as his “alter ego,” pocketing the profit when stocks in the fund went up, and letting the fund take the loss when they went down (the CIA eventually lowered the “national security” curtain on Wright Patman, thereby saving Jacob Kaplan from criminal prosecution in shutting down the probe). Earlier, the CIA used Kaplan to travel to Havana and try to make a deal so favorable to Cuba only a socialist would turn it down.²⁶ A sweetheart deal, so to speak. But Castro, perhaps mindful of Prío's counsel, turned it down. For the CIA, this was “proof” of Castro's leftist leanings.

There is an incredible sidebar to the Kaplan collaboration story. It involves Jack Kaplan's nephew, Joel David Kaplan, a traveling executive of Jack Kaplan's Southwestern Sugar & Molasses Company, which had widespread operations in the Caribbean region.²⁷ Joel was privy to the arrangement in which the Kaplan Fund would be used as a conduit for funds to be distributed to left-of-center labor unions in the region to forestall any power grab by leftist elements, as had happened in Cuba.

But Joel was sympathetic to Castro's revolution, largely because of the abject poverty he had seen in his travels. The CIA was using Southwestern facilities to forward military supplies to bases in Guatemala intended as springboards for the Bay of Pigs invasion. In his position as a company executive, Joel Kaplan was able to divert the supplies to Castro-oriented units.28 The CIA did not discover the treachery until after the invasion had failed. But Joel was an ongoing threat. Since he was Uncle Jack's close relative, murdering him was not an option.

Instead, Joel was framed in Mexico for a murder of a business partner, despite the fact that the body was patently not his. The putative murder victim was Luis Vidal Jr., son of a Dom Rep lobbyist. Joel's sister, Judy Dowis, got Warren Hinckle and this author interested in Joel's story, and in July 1967, I interviewed him in Lecumberri Prison in Mexico City. Joel recalled that Luis had boasted that “the old man had clean access to the White House—all the way up to Ike himself.” Luis also showcased the claim that he was somehow related to Jacqueline Bouvier Kennedy. It may have been possible, since JFK himself was Trujillo's godson, thanks to the elder Joe Kennedy's idea of class. It was an anthropologist's nightmare.

The darkly handsome Vidal disappeared, coincident with the discovery of a body on a Mexican highway. It in no way resembled the playboy, but Joel was promptly arrested, tried, and jailed, and Vidal was heard from no more.

The CIA had Joel where it wanted him, but help was on the way. After Joel lost all appeals, his sister, who had been underwriting escape plots, insisted that I interview him in prison. He was obviously depressed underneath his prison pallor. As I scribed in my diary, “He just looked blank when I asked him if he was a CIA agent. He claimed his partner wasn't really dead. He kept mentioning Havana, saying I'd find some answers there. He told me that he had been framed but seemed reluctant to say who had framed him.” Joel kept repeating, “Someone else's money was involved.” I asked whose money, but the guard halted the interview and Joel was led away.

It was clear from the powerful forces arrayed against Joel that escape was his only way out. Several escape plans were tried, mostly involving bribery of Mexican officials, then a daring aerial one, proposed by Joel and developed by Vic Stadter, was selected.²⁹ Vic was a Californian with the style of a Texan, and he was a smuggler known by practically every Customs inspector on the US–Mexican border. Vic was the last of the rugged individualists who believed in the right of man to operate free of the restrictions of bureaucracy. He had been working on escape plans with Joel's sister, Judy, for several years when Joel was moved from Lecumberri to Santa Marta Acatitla Prison, high in the mountains outside Mexico City. On the evening of August 18, 1971, a helicopter descended into the prison courtyard in sight of the prison tower guards, who were frozen in place, not sure if it was the attorney general's helicopter, since Vic had painted it the same color as the attorney general's fleet. The helicopter pilot had been instructed to land in the courtyard, then count to ten and take off. Joel and his cellmate raced across the courtyard and scrambled onboard the helicopter, which took off immediately and disappeared into the night sky.30 Joel linked up with a small plane in the outskirts of Mexico City and was flown to Stadter's house near Glendora, California. Vic knew all the smugglers’ routes to avoid detection.

Warren Hinckle and I used Vic's home as a safe house to debrief Joel. From that debriefing, Hinckle and I produced a book, The Ten Second Jailbreak, which was later turned into a movie by Columbia Pictures, called Breakout, starring Charles Bronson and John Huston. Our book was a tough indictment of the CIA's role in Joel Kaplan's predicament, but in the process of making the movie, the CIA apparently got into the act and forced a rewrite that resulted in a Grade B potboiler. But the casting was superb.

Vic and Joel, the cowboy and boarding-school grad, later teamed up in business, speculating in gold. When last heard from, they were riding into the sunset in New Mexico.