U.S. spy freed by Cuba was longtime asset
By Adam Goldman
December 18, 2014
The Cuban government on Wednesday freed a U.S. spy whom President Obama described as one of most important intelligence agents that the United States has ever had in the Communist country and who helped unravel several long-running Cuban espionage operations.
U.S. officials said the release of the Cuban-born spy, identified as Rolando Sarraf Trujillo by a U.S. official, was a major priority for the intelligence community as part of any deal with the Cubans. That agreement,  Obama said, also included the exchange of three Cuban spies by the United States and the release of former U.S. aid worker Alan Gross by Cuba on humanitarian grounds.
The choreographed exchange ranked as one of the most significant spy swaps in recent memory and came four years after the United States exchanged 10 "sleeper" agents with Russia  in return for the release of several Russian nationals who had spied for the West.
Little is known about Trujillo other than that he had been imprisoned for nearly two decades and presumably had been working on behalf of either the FBI or the CIA long before that. Trujillo's identity -- first disclosed by Newsweek.com  -- was later confirmed by a senior American official, who spoke on condition of anonymity.
In a highly unusual disclosure, the Obama administration on Wednesday revealed specific operations that the spy had helped the United States penetrate, saying he provided critical information that led to the arrests of those known as the "Cuban Five;" of former State Department official Walter Kendall Myers and his wife, Gwendolyn Steingraber Myers; and of the Defense Intelligence Agency's top Cuba analyst, Ana Belen Montes. 
Although the U.S. intelligence community is believed to have significant operations in Cuba, the existence of a single asset who was instrumental to so many high-profile counterintelligence cases was previously unknown.
While U.S. officials say the spy was ranked among the United States's best assets in Cuba, a former senior CIA official said there was another alongside him, an individual known as "Touchdown," who defected in the late 1980s. Touchdown revealed that many of the CIA's assets in Cuba were double agents.
The Myers investigation was one of the most serious espionage cases involving the State Department in recent years. The FBI long suspected there was a mole in the agency but did not have a name.
In 2009, as part of its counterintelligence operations, the FBI launched  a "false flag" operation against the Myerses involving an undercover FBI agent posing as a Cuban intelligence emissary. In a string of recorded meetings, the couple described their ties to the Havana government. They would later plead guilty to spying.
In 2010, the husband was sentenced to life in prison; his wife received nearly seven years. The FBI did not disclose in its indictment how law enforcement officials initially learned about the couple's activities.
Montes, the DIA analyst, was also spotted early by the Cuban government in a "classic tale of recruitment,"  according to the FBI. In 1984, Cuban officials learned she was "sympathetic to their cause," and she soon agreed to help, landing a job at the agency in 1985.
According to the FBI at the time, it was a DIA colleague who reported her in 1996 to a security official, suspecting she might be "under the influence of Cuban intelligence." The bureau made no mention of its secret asset in Cuba, likely to protect him, even though he was already in prison.
Montes was arrested days after the Sept. 11, 2001, terrorist attacks and pleaded guilty in 2002. She was sentenced to 25 years in prison.
Another woman, Marta Rita Velazquez,  whom the FBI said introduced Montes to Cuban intelligence, was charged in 2013 with conspiracy to commit espionage. Velazquez, of Puerto Rico, lives in Sweden.
It's unclear what role what the spy identified as Trujillo played in the arrest of the Cuban Five -- three of whom were released Wednesday and two of whom were released from prison earlier. But, as in the other cases, he appears to have provided information to U.S. intelligence before he was imprisoned in Cuba.
According to the indictment of the Cuban Five, U.S. authorities learned as early as 1995 that Cuban intelligence had sent operatives to the United States.
The U.S. intelligence community issued only a brief statement after the spy exchange on Wednesday.
"Information provided by this person was instrumental in the identification and disruption of several Cuban intelligence operatives in the United States and ultimately led to a series of successful federal espionage prosecutions," said Brian Hale, a spokesman for the Office of the Director of National Intelligence.
Hale added it was a "fitting closure to this Cold War chapter of U.S.-Cuban relations."