No one ever said authoritarians played fair. While denying Cuban citizens access to international media, Fidel Castro was a voracious consumer of CNN and the New York Times, says Paul Hare, who should know. Hare met Castro several times while serving as the British ambassador to Cuba from 2001 to 2004.

Hare, now a Pardee School of Global Studies senior lecturer, says Castro’s death last month at age 90 marked the end of the most important Latin American leader of the last century: a man who toppled Cuba’s US-friendly dictator in 1959 and turned his tiny nation into a thumb in the eye of its American neighbor. His rule, ending when he transferred power to his brother Raul in 2006, spanned from the Cold War (he allied with the Soviet Union and became dependent on its subsidies) to the 21st century, and during that time his country achieved significant improvements in health care and education—while its economy remained stagnant and political repression of his enemies flourished. Last year, Raul Castro and President Obama negotiated normalized relations between the two nations.

Bostonia asked Hare for his take on Castro’s life and death, and the future of Cuba without him.

Bostonia: You met with Fidel Castro when you were British ambassador. What was he like in person?

Hare: I met Fidel at state occasions, in small gatherings, and at public events. He was usually only accessible when ministers from the UK visited, and then not every time. He was becoming less sociable with diplomats compared to earlier years. But I have also met several of his children, as well as Raul’s daughter and wife.

How would you sum up his legacy, balancing the pros (progress in health care and social equality) and the cons (economic distress and political repression)?

His legacy was to build a nation where he and his ideas were the main defining feature. Either you were with Fidel or you were against him. If you disagreed in public, you would be harassed or imprisoned. Many chose to leave. Those who stayed saw Cuba become a center of world attention—unique in world history for such a small country. This was due to the force of Fidel’s personality, his success in defeating the US Bay of Pigs invasion in 1961, and his relative youth.

He used Soviet subsidies to build education and health care and fund his military adventures. Cuba became a society where the government provided for everyone, but only on its own terms. Ultimately, he never trusted ordinary Cubans to build their lives and decide how they wanted to view their government and contribute to society. He decided everything for them and paid them so little they were always dependent on the government. So now the government needs new sources of income because of the collapse of the Soviet Union and the decline of Venezuela [an ally hurt by plunging oil prices]. Ironically, among Cuba’s greatest sources of hard currency are the remittances from Cuban Americans, and they are now helping their families start small businesses.

Castro’s mixed legacy of social progress and repressive dictatorship was captured in Miami, where Cuban Americans celebrated the revolutionary leader’s demise. Photo by Getty Images/AFP

How does Castro rank, historically, in importance as compared with other Latin American leaders?

In my view, he is the most important figure in Latin American politics for over 100 years. No one compares in the history of Cuba.

Will his death affect US-Cuban relations and his country’s role in world affairs?

Yes. The Obama era has built up a wary trust between the two countries over several years of conventional and unconventional diplomacy. That may now change under president-elect Donald Trump’s vow to do a better deal. Such a change would be unpopular with many Cuban Americans, who have been visiting Cuba frequently to help families in business and to improve their homes. If Trump were to close off Cuba to US products and tourism, this would damage a lot of businesses. And 33 states now have Republican governors, so many of these will not be overjoyed to leave these opportunities to their competitors. Cuba simply has to open up to the market and international investment. There is no alternative.

Cuba will also lose its allure, and Raul’s expected retirement as president in 2018—which may now be rethought—will mean Cuba will be seen more and more as just another country competing for investment and tourism.

Fidel pooh-poohed President Obama’s normalization of relations. How influential were his criticisms with average Cubans?

I don’t think Fidel’s opposition to Obama’s opening relations influenced ordinary Cubans. They see the opening as more in their own economic interests than anything else and hope for a full lifting of the US embargo. That, of course, has not been in Obama’s executive power to grant.

Can you envision what a totally post–Castro family Cuba will be like?

With Fidel gone and much more reforming to be done, I think Raul might rethink his departure, or perhaps install a Castro family member in a new economic role. There are lots of sons (Fidel had at least seven), and Raul has a son, a son-in-law, and a daughter who have prominent roles. Though Fidel has had little day-to-day control for a decade, his departure will need careful handling, and Raul will not want to appear to be dismantling parts of his brother’s revolution, such as expanding the private sector beyond its currently small confines. But Raul is known to like the Chinese path, where a one-party state readily accepts that people can get rich and inequality can flourish, providing they don’t meddle in politics