Fidel Castro once called George W. Bush a "functional illiterate".
Ronald Reagan was "the worst terrorist in the history of mankind," Castro said, with ideas "from the Buffalo Bill era".
Castro thrived on confrontation with US leaders, and he almost surely would have enjoyed facing off against America's next one.
In his statement on Castro's death, US President-elect Donald Trump denounced him as "a brutal dictator," and that's the sort of dig that wouldn't have gone unanswered in the past.
But brinkmanship and barb-throwing are not the forte of his successor, Raul Castro. Raul Castro, 85, has refrained from criticising Trump and even sent congratulations after his win.
Raul Castro's plans to secure the legacy of his brother's 1959 Cuban Revolution appear to be on a collision course with the incoming Trump Administration, whose top members said that Cuba would have to make significant "changes" in order for the normalisation path charted by US President Barack Obama to continue.
If tensions between Cuba and the United States ratchet up again under a Trump presidency, it would be a new stress test for Raul Castro and his quieter, more austere leadership style. Cuba will enter the Trump era with Fidel Castro's one-party socialist state firmly in command but without the super-charged politics and nationalist fervour he relied on to sustain it.
A return to more hostile relations with the United States could also bring a new crackdown in Cuba and further slow the pace of Raul Castro's modest liberalisation measures at a time of stalling economic growth. Hardliners in Cuba's Communist Party would gladly take the country back to a simpler time, when the antagonism of the United States - not the failure of government policies - was to blame for the island's problems, and the threat of attack, real or imagined, was used to justify authoritarian political control.
On Fox News, Reince Priebus, Trump's incoming chief of staff, said: "There's going to have to be some movement from Cuba in order to have a relationship with the United States". Castro would have to take steps to allow more political, economic and religious freedoms, Priebus said.
Obama announced in December 2014 that the United States would re-establish diplomatic relations with Cuba, which were severed in 1961. Trump said during his campaign that Obama didn't get a good "deal," and Cuba must do more. While only the US Congress can lift the Cuba embargo, Trump could reverse many of the executive orders that have brought a surge of US visitors to Cuba and a rush of new interest from American companies.