Tupac’s Cop-Killer Aunt Chilling In Cuba May Finally Face Justice In U.S.

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JP Carroll National Security & Foreign Affairs Reporter
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Cuba and the U.S. might engage in a prisoner swap straight out of a spy thriller involving a Cold War era spook and Tupac’s aunt, according to a Friday report from NBC News.

The two former Cold War enemies are in talks that could lead to the U.S. handing over convicted spy Ana Montes to the Cubans in exchange for the cop killer Assata Shakur, the aunt of the rapper Tupac Shakur. Montes was nabbed in September 2001 on espionage charges for giving U.S. secrets to Havana for almost two decades while at the Defense Intelligence Agency (DIA). Shakur busted out of a New Jersey jail in 1979 where she was serving life for murdering a state trooper; the aunt of rap royalty has been laying low in Cuba since the mid-1980s.

Montes, a Latina modern-day Benedict Arnold leveraged her position as an analyst at DIA to secure top flight information for her Cuban handlers. Montes was so cunning and effective that she was DIA’s most trusted Cuba analyst before her career came crashing down as her treason was revealed.

The former DIA analyst received a 25 year sentence and should be out in 2023. Montes’ spying was so damaging to the U.S. intelligence community’s efforts against the Castro brothers’ regime that it was, “calling into question the reliability of all U.S. intelligence collected against Cuba,” according to national security expert and former official Michelle Van Cleave, who spoke with NBC News.

While Shakur did not damage the U.S. intelligence community, her crime is shocking its own right. Shakur gunned down a state trooper, with his firearm, at a routine traffic stop according to NBC News.

A State Department spokesman told NBC News, “The United States continues to seek the return from Cuba of fugitives from U.S. justice. The Department repeatedly raises fugitive cases with the Cuban government and will continue to do so at every appropriate opportunity.”

Montes does not seem particularly remorseful for being one of the most infamous spies in recent U.S. history. In a letter to a friend, Montes said, “I believe that the morality of espionage is relative,” according to The Guardian. The treasonous former intelligence officer went on to write, “The activity always betrays someone, and some observers will think that it is justified and others not, in every case.”

The spy admitted to investigators that she was seduced by the reasoning of her Cuban handlers who told her, “tried to appeal to my conviction that what I was doing was right.” Montes was lured into her dangerous double life by a classmate in graduate school at Johns Hopkins University’s School of Advanced International Studies.

When the DIA analyst was arrested, Montes was the equivalent of a colonel. According to publicly available information, Montes is the highest ranked Cuban asset to have ever spied against the U.S.

A Department of Defense Inspector General report from 2005 that was declassified in 2014, states that Montes betraying her country was something she was “coolly deliberate” about, according to excerpts from The Miami Herald. Once she was arrested, Montes admitted that she felt there was a “mutual respect and understanding” since they were “comrades in the struggle.”

The Obama Administration normalized relations with the Cuban government in December 2014 meaning the reestablishment of direct diplomatic ties. In 2015, the two countries re-opened embassies in one another’s capitals. President Obama subsequently made a historic trip to Cuba in March, making him the first U.S. president in almost 90 years to visit the island country.

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