Barack and Fidel: like so many great love affairs it was doomed. But memory of the passion, or at least infatuation, lingers.
Having seen off 10 US presidents - all committed to his assassination, overthrow or isolation - Fidel Castro had more reason than most to beware the occupant of the Oval Office.
But Barack Obama was different. The octogenarian communist revolutionary fell for the young new president and became "obsessed", according to confidential US diplomatic cables released by WikiLeaks.
Having confidently predicted the US would not elect a black man, Castro sat bolt upright when the candidate of hope and change swept to the White House. His Reflections columns in the communist party newspaper, Granma, were filled with observations about, then praise for, Obama.
The US diplomatic mission in Havana, long accustomed to reporting the commandante's diatribes against American tyranny, was not prepared for fan mail.
"Fidel's subsequent Reflection on 9 June will only add to speculation from our civil society and diplomatic contacts that Fidel is obsessed with President Obama," said one memo.
Obama's speech in Cairo on US relations with Muslims inspired a 3,500-word response from the retired Cuban leader in which he lauded Obama as a "very good communicator" with "impressive working capacity". Coming from a workaholic famous for marathon speeches, this was praise indeed.
He noted that the president of the US, called "Potus" in the cables, took office at an "exceptionally complex time" and could not be blamed for the Middle East quagmire he inherited.
"Fidel mostly sympathised with Potus - in his own way," said a memo from Jonathan Farrar, the US chief of mission. "Fidel then continued his attempts to walk a thin line between a positive impression of a popular US president and the idea that the evil empire will never change."
In other Reflections columns, the US nemesis who called George Bush a genocidal drunk praised Obama as intelligent, sincere, serene, honest and well-meaning. He welcomed the president's Nobel peace prize and called his position on global warming courageous.
Latterly, the commandante's ardour for Obama began to cool, with a tone of disappointment and sense of betrayal over the president's stance at the Copenhagen climate change summit.
"Following the conference, Fidel wrote three straight Reflections devoted to attacking President Obama's participation in Copenhagen. Fidel called President Obama's conference remarks 'deceitful, demagogic and ambiguous,'" a cable said.
Cuba's leader, it noted, had taken to calling Obama the "yanki president".
US diplomats were left isolated and afraid that Cubans were intercepting every call after secure phone lines were cut at the mission in Havana, a leaked cable shows.
They complained to Washington that the mission could not function properly until the technological glitch was fixed.
"Post is experiencing extreme difficulty establishing secure voice calls," a classified dispatch said in January 2010.
Several solutions had been tried but secure voice calls were unable to be established, it said.
"This has left post with no secure voice link to Washington or other missions. As post operates in a critical technical threat environment, this situation is unacceptable and post needs assistance in resolving the situation expeditiously."