#10: Ana Montes — United States
Ana Montes became one of the Defense Intelligence Agency’s leading Cuba analysts while secretly reporting to Havana for roughly seventeen years. Unlike many spies, she was motivated chiefly by ideology rather than money. She memorized classified material, typed it later, and communicated through coded messages. Arrested shortly after the September 11 attacks, Montes pleaded guilty in 2002 and received twenty-five years. She was released in 2023 after serving most of that sentence under strict supervision.

