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When they first met, at a 1991 Palacio de la Revolucion celebration, Fidel Castro asked Vicki Huddleston if she was someone’s spouse.

She told him she was the director of Cuban affairs for the United States.

“Oh? I thought I was!” Castro said.

Huddleston (IntlAf’64) — the top U.S. diplomat in Cuba from 1999 to 2002 — held the position at a time when few women held a comparable rank. And despite Castro’s initial condescension, she found that being a woman was to her advantage.

“I felt I was more personally involved with the Cuban people and Fidel Castro, because Castro liked women,” she said over the summer from her home in Santa Fe, N.M.

In a distinguished diplomatic career that began in 1976, following service in the Peace Corps in Peru, Huddleston served not only in Cuba — the main subject of her recent memoir, Our Woman in Havana — but also as U.S. ambassador to Madagascar and Mali.

The book explores the tense history of U.S.-Cuba relations while recounting rich anecdotes from her own experience — of the saga of Elian Gonzalez, the 5-year-old Cuban boy who was the subject of a fierce international custody battle, of the aftermath of the Sept. 11 attacks and of Fidel Castro himself.

It also clarifies why Huddleston felt being a woman was helpful.

As head of the U.S. Interests Section, she implemented programs intended to empower the Cuban people to engage with the wider world. She and her staff provided access to uncensored devices and information by handing out books and portable radios. They also hosted dissidents in their homes to help activists make connections.

“A male ambassador would not have done what I did,” Huddleston said. “I think in a way it would have been beneath him to be handing out radios.”

Castro’s notorious fondness for women helped.

“Fidel was more open to working with a woman,” Huddleston said. “So there was always a possibility of finding a way open [between the U.S. and Cuba]. I don’t think there are any kind of personal relationships now.”

Huddleston’s memoir offers a window into the start-and-stop, forward-backward nature of U.S.-Cuba relations over the past two decades.

When she arrived in 1999, the U.S.’s trade embargo was still firm. But the Clinton administration eased travel restrictions and enabled relations with the Cuban government. The Bush administration initially continued this, before reverting to stricter policy.

In 2002 Huddleston left to become U.S. ambassador to Mali. Soon afterward, Castro jailed 75 dissidents and Huddleston’s radio and book distribution program stalled.

“I didn’t agree with anything the [U.S.] administration was doing,” she said.

Huddleston still follows foreign affairs closely and expresses frustration with U.S.-Cuba policy, increasingly fraught after seeming improvement during the Obama years. She hopes her book will convince readers that hardline U.S. policy has failed.

“And not only that it failed,” she said, “but that when we are more open, Cuba is more open.”

Photo courtesy the Overlook Press