One possibility that US officials – including Trump – have floated is that new leadership could take over in Havana.
This playbook, experts have noted, could be similar to Maduro’s replacement with Delcy Rodriguez in Venezuela, which left the government largely intact, albeit dealing directly with the Trump administration.
Trump has repeatedly said he is already dealing with figures inside Cuba who hope for US help amid worsening economic woes.
“Cuba is asking for help, and we are going to talk,” he wrote on Truth Social on 12 May.
Days later, CIA Director John Ratcliffe met Cuban officials, including Castro’s grandson, Raúl Guillermo Rodríguez Castro, and Interior Minister Lázaro Álvarez Casas.
“We’ll engage with the Cubans… at the end of the day they need to make a decision. Their system just doesn’t work,” Secretary of State Marco Rubio told reporters in Florida on Thursday, adding that the administration’s preference is a “negotiated agreement”.
The changes that the US wants could include a pledge to open up the economy, invite more foreign investment and involvement by Cuban exile groups, as well as a commitment to end the presence of Russian or Chinese intelligence agencies on the island.
Importantly, these changes could leave Cuba’s government largely intact.
“Just like they wanted to avoid instability in Venezuela, they want to avoid instability in Cuba,” said Michael Shifter, a professor of Latin American studies at Georgetown University and the former head of the Washington-based Inter-American Dialogue, a think tank.
“Forcing a regime change would be too risky for that,” he added.
Several experts contacted by the BBC said that the challenge for the Trump administration is that there is no immediately obvious figure waiting in the wings inside Cuba.
“I don’t think there’s an obvious Delcy Rodriguez in Cuba, and power works differently in Cuba than in Venezuela,” Shifter said. “It’s hard to find what they’re looking for, but I do think they’re looking for some sort of governing structure.”