Howard’s trip to Havana in the winter of 1964 was pivotal in advancing one of the most unusual and consequential partnerships in the history of U.S.-Cuban relations. She became Castro’s leading American confidant, as well as his covert interlocutor with the White House—the key link in a top-secret back channel she singlehandedly established between Washington and Havana to explore the possibility of rapprochement in the aftermath of the Cuban missile crisis.

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