Hare on U.S. Pressure, Leadership Change, and the Future of U.S.–Cuba Relations
In a featured Q&A titled “Will Díaz-Canel Be Able to Finish His Term in Cuba?” for the Latin American Advisor, Paul Webster Hare, former British ambassador to Cuba and a master lecturer at the Pardee School of Global Studies, offered sharp analysis on the Trump administration’s renewed pressure campaign against Cuba and its implications for leadership change on the island.
As reports suggest Washington hopes to see President Miguel Díaz-Canel pushed from office before the end of his term, Hare emphasized that any U.S. effort would be driven by a desire to demonstrate tangible results. “If the U.S. pressure on Cuba works, the Trump administration will want to show results,” he noted, while cautioning that external factors—such as continued Russian oil deliveries—may blunt that pressure.
Hare drew parallels between U.S. objectives in Cuba and Venezuela, arguing that Washington appears to favor leadership reshuffles that preserve underlying power structures rather than democratic transformation. He warned that replacing Díaz-Canel with another figure tied to the Castro family could amount to a symbolic victory rather than meaningful political change. “Any successor to Díaz-Canel needs to be acceptable to the Castros or the leader will be seen as an American puppet,” Hare explained, adding that the U.S.-backed outcome in Venezuela has done little to restore democracy there.
Looking ahead, Hare suggested that Cuba may respond pragmatically by offering business opportunities to U.S. companies in sectors such as tourism, agriculture, and energy—opportunities that could have emerged years earlier under the Obama-era normalization efforts. He also highlighted divisions within the Cuban-American community over whether to prioritize rapid regime change or incremental economic reform. In this uncertain landscape, Hare argued, unified political leadership will be critical, underscoring that sustained diplomatic outcomes depend not only on pressure, but on coordination, legitimacy, and long-term strategy.
The full Q&A can be read here.
Paul Webster Hare is a master lecturer at the Frederick S. Pardee School of Global Studies. He served as British Ambassador to Cuba from 2001 to 2004 and also represented the U.K. to the European Union in Brussels, New York, Portugal, and Venezuela as deputy head of mission. Hare has extensively written about Cuba for renowned news outlets including The Financial Times, The Atlantic, Newsweek, and The Huffington Post. He is also the co-editor of the Palgrave Handbook of Diplomatic Reform and Innovation, which analyzes current practices of diplomacy and proposes practical solutions to improve diplomatic outcomes.