Chris Simmons has been a Counterintelligence Officer since 1987 and a Latin Americanist since the early 1980s.  From 1996-2004, he was deeply involved with the majority of US Counterintelligence successes against Cuba.  He was a central figure in the identification, investigation, and debriefing of convicted Cuban spy, Ana Belen Montes.

She remains the highest-ranking Cuban spy ever sent to prison in the US.

Simmons was the lead military official in the May 2003 expulsion of 14 Cuban spies serving under diplomatic cover. This was the third largest expulsion of diplomats in US history, and the only one not targeted against Russia/USSR.

He has lectured on Cuban Intelligence throughout the US Intelligence Community, to members of Congress, academia, a major Washington DC think tank, and on radio and television. From 2007-2008, he wrote a column on Cuban Intelligence for the Miami Herald.  He retired from the Defense Intelligence Agency in December 2007.