This candid memoir features many revealing and entertaining anecdotes from Huddleston’s time as head of the U.S. mission in Havana, a position she held from 1999 to 2002. (Without an embassy of their own, U.S. diplomats used the Swiss one instead.) When Huddleston rst met Cuban President Fidel Castro, she introduced herself as “the director of Cuban a airs”; Castro boomed back, “Oh? I thought I was!” Huddleston also discusses the political pressures under which she operated. U.S. policy toward Cuba was driven largely by militant anti-Castro Cuban exiles in Miami, whose leadership Huddleston paints as vengeful and delusional. As a result, U.S. diplomats concentrated on connecting with dissident activists on the island, even though they did not pose “the slightest threat to Castro’s rule.” Later, in 2006, when Raúl Castro assumed power, the U.S. mission, still focusing on the wrong things, failed to fully brief Washington on Raúl’s reforms and the opportunities they presented for better relations. By the time the Obama administration engaged with Cuba, in late 2014, it was too late to make the new, warmer relationship politically irreversible—to the eventual delight of anti-Castro Cuban Americans in Miami and U.S. President Donald Trump, who has undone much of the progress Barack Obama made.