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CRAFT: The Queen of Cuba

CRAFT: The Queen of Cuba
Photo illustration by Ryan Ho
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Ana Montes was known among her colleagues at the Defense Intelligence Agency as the "Queen of Cuba" due to her exceptional expertise on the country. Little did they know she was a Cuban spy.


Back in the 1990s, Ana Montes was known by her colleagues at the Defense Intelligence Agency as the "Queen of Cuba" due to her exceptional expertise on the country.

Little did they know that Montes was also a prized asset to the Cubans, who had recruited her as a spy. Montes leaked classified information to the Cuban government for 17 years.

Eventually, suspicions arose and an intense FBI investigation led to Montes' arrest in September 2001. After admitting to revealing the identities of four American undercover intelligence officers in Cuba, she was found guilty of conspiring to commit espionage against the United States.

Recently, Montes made headlines again after being released from a lengthy prison sentence at the start of the year. Now 65, she lives in Puerto Rico and continues to speak out against the U.S. sanctions against Cuba, although her internet usage will be monitored for the next five years.

Montes receiving a national intelligence certificate of distinction from George Tenet, former Director of Central Intelligence (DCI), for CIA.

I had the opportunity to speak with Peter Lapp, a retired FBI agent who spent 22 years working in the Bureau of Counterintelligence and Counterintelligence Espionage. He shared insight on the FBI's investigation to identify Ana Montes, the Cuban spy. From discovering there was a spy within the U.S. government to ultimately identifying the agency she worked for, Lapp explained how tracking her down was a complex and challenging effort.

A quick note. Today we launched a podcast called THE CLOSER, a new series and newsletter all about the world of deals. Please check it out and let us know what you think. – Bradley

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