18: Controlling Cuban-Exile Chaos

Publicly Vice President Richard Nixon was asserting that the U.S. should take a hands-off approach to Cuba and hope for the best.1 But in fact, Nixon had been dealing with the issue of Castro since at least April 19, 1959, when he met with Castro and then “prepared a 4-page secret memorandum and sent out copies to President Eisenhower, Secretary Herter and to Allen Dulles.” Herter was serving as Secretary of State in place of an ailing John Foster Dulles who coincidentally was hospitalized at the same time as former Secretary of State George C. Marshall. Dulles died May 24, 1959, while Marshall passed October 16, 19592 leaving a hole in William and Edna Pawley’s personal lives and William’s sphere of influence.

In the 12 months since Castro ascended to power, the Cuban government had expropriated 70,000 acres of property owned by U.S. sugar companies and United Fruit. Once again, the company would call for U.S. action to overthrow a government.3 

The tsunami of Cuban exiles arriving in the U.S. made that mission seem easy if someone could vet them to determine the best future political leaders and organize an effective fighting force.

On January 3, 1960, President Eisenhower announced that the U.S. was severing diplomatic relations with Cuba. On January 13th a Special Group meeting attended by CIA Director Allen Dulles and Livingston Merchant from the State Department discussed “Anti- Castro Activities.” With these actions and Eisenhower's March 17th approval of a plan to invade Cuba, he was in essence establishing an undeclared war that would hang like an albatross around Uncle Sam’s neck.

The CIA began dealing with Fidel on a formal basis on January 8, 1960, when Director Allen Dulles asked Deputy Director of Plans Richard “Dick” Bissell to organize a special task force. Ten days later the Western Hemisphere Division “organized Branch 4 (WH/4) as an expandable task force to run the proposed Cuban Operations” manned “with 18 at Headquarters, 20 at Havana Station, and 2 at Santiago Base.”

Heading WH/4 was Jacob “Jake” D. Esterline (aka Jacob Engler) who had gained “extensive guerilla warfare experience in World War II with the OSS” and was “one of the principals in Project PBSUCCESS” in Guatemala in 1954. “Esterline was the choice of J.C. King, Chief, WH Division.” As head of the WH/4 Cuban unit during the fifteen-month run up to the Bay of Pigs invasion, Esterline took his orders from the Deputy Director Plans Richard Bissell but frequently had direct contact with J.C. King and the Miami-based Cuban expert, William Pawley. Both were to be reckoned with because they “had known Republican Party affiliations.”4

King’s full role during the period and many interactions with Pawley will never be known. His papers that once filled eight safes—then only two—disappeared, according to an official history of the period.5

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31: JFK Disapproves the Somoza Plan Backed by Pawley

After Operation TILT, William Pawley turned his attention to General Luis Somoza's plan to invade Cuba from Nicaragua with hopes it would justify full U.S. intervention, while John Martino shifted his energy to a new project involving Rolando Masferrer Rojas and an invasion of Haiti in August 1963. The common goal was to eliminate Castro.

A CIA telegram stated, “According to Carlos Zayas Castro, a colleague of Rolando Arcadio Masferrer Rojas, and several other unidentified persons in the Miami area, the recent Haitian activities were organized and supported by Masferrer, a Cuban exile who travels between New York and Miami. (Field comment: General Leon Cantave is generally credited with having organized the 5 August invasion of Haiti. Masferrer may have been seeking personal aggrandizement had the invasion been successful.)”

The telegram further noted that Masferrer “had Cubans in place in the Dominican Republic and in Haiti; he attempted to recruit 30 men from the Commandos L Group through Zayas.” Masferrer planned “to establish Carlos Marquez Sterling, a leading Cuban exile, as the figurehead or President.” Without addressing the source of his money, the telegram stated that “John Martino financed the travel of about 200 Cubans from New York to Miami” who as of August 8th were staying “in the Senate Hotel [probably the Art Deco Senator Hotel on Collins Avenue at 12th Street] and another hotel in Miami. Martino did not know what to do with his men following the collapse of the Haitian invasion.”1

Rolando’s brother, Raimundo Masferrer, who moved to Dallas in 1958 where he worked for the Parks Department as a mechanic, helped raise money for arms, believing the invasion would pave the way to overthrowing Castro who had imprisoned six of their family members and whose forces shot six others in 1959.2

In January 1960, William Pawley had advised the CIA that he had been contacted by Arthur Patton, a Commissioner from Dade County, Miami, Florida, who asserted that one of his police officers had been offered $200,000 to kidnap another of Rolando’s brothers, Rodolfo “Kiki” Masferrer.3

Rolando Masferrer had come to the attention of the intelligence agencies as early as 1948.4 He tried to endear himself to Trujillo in 1956.5 After arriving in the U.S., Rolando lead exile raids against Castro.6 Prior to the Bay of Pigs, the CIA tried to neutralize his activities against Castro7 and the Kennedy Justice Department later indicted Masferrer for plotting an invasion against Cuba.8 He then turned his attention to trying to overthrow Duvalier in Haiti, in the summer of 1963.9

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