Masferrer participated, with Fidel Castro and over 1,000 Cubans, in the aborted Cayo Confites expedition of 1947, which sought to overthrow Rafael Trujillo, the authoritarian leader of the Dominican Republic.

In this period he published two papers Tiempo in Havana and Libertad in Santiago de Cuba which insulted Francisco Franco, but without positive reaction among other leftwing Spanish Civil War exiles.

[6] During the final years of the last Batista regime to the end of 1958, Masferrer and his Tigres operated in Oriente province; from headquarters in Victoria de las Tunas, or others claim from Santiago, Manzanillo and Bayamo[7] He had an array of weapons including lethal large caliber "air rifles."

He is known to have threatened Franciscan priests in Manzanillo, Cuba[8] The Cuban government of Fidel Castro accused Masferrer of 2,000 killings - disputed by some - and said the Tigres were careful to remove all evidence.

[7] Masferrer plotted to buy "La Hacienda Sevilla" and divide up the land so as to reward the local guajiros for informing on Fidel Castro in the first months of his operations in the Sierra Maestra.

He fled on his yacht Ola Kun II, a former U.S. Coast Guard vessel with his family and over twenty followers on 1 January 1959, arriving in Key West, Florida.

Castro accused to Masferrer of stealing U.S. $17 million (disputed), and requested to the U.S. government the extradition of Rolando, back to Cuba.

One boat reached the island, three Americans: Allan D. Thompson, Anthony Zarba and Robert O. Fuller were caught and eventually executed[10] In December, 1960, the Miami Herald, reported that Masferrer was leading a group of 53 people, undertaking training for assassination at a ranch owned by multi-millionaire Howard Hughes.

[citation needed] In the early 1960s, Masferrer was associated with El Tiempo, a Spanish-language newspaper, edited by S. Ross, in New York City.

[citation needed] In 1967, Masferrer plotted and accumulated weapons to invade Haiti so as to have a base, free of U.S. law, to attack the Castro government which had foiled direct attempts to land (Project Nassau or Operation Istanbul).