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On February 24, 1996, Cuban fighter jets shot down two small planes operated by Brothers to the Rescue, an organization in Florida that tried to spot refugees fleeing Cuba in boats. A strange chain of events preceded the shoot-down, and people in the intelligence business turned to a rising star in the Defense Intelligence Agency, Ana Montes. Montes was known around Washington as the “Queen of Cuba” for her insights into the Castro regime. But what Montes’ colleagues eventually found out about her shook their sense of trust to the core.

The Host

Malcolm Gladwell

Malcolm Gladwell is president and co-founder of Pushkin Industries. He is a journalist, a speaker, and the author of six New York Times bestsellers including The Tipping Point, Blink, Outliers,…