In 2000, Vladimir Putin met Fidel Castro in the context of a warming of US-Russian relations. Not long afterwards, he decided to close down a military base on the island dating back to the Cold War. Cuba lost millions in rent payments, infuriating Castro.
But President Dmitry Medvedev is keen to improve ties once again.
“This is not just a Russian president going on a study trip with his colleagues and journalists,” he has said of his visit. “This was a serious geo-political decision. We will develop our relations with Latin American and Caribbean countries.”
Observers say this is a resurgent Moscow, flexing its muscles and taunting Washington in its own traditional backyard. It is about a renewal of historical Cuban-Russian ties.
When Castro came to power in 1959, his revolution was at first nationalist, but he quickly moved towards a pro-Soviet stance. This, at a time when the island was increasingly at odds with the US.
It was during this context that one of the biggest crisis’ between the two super powers broke out in 1962 – the Cuban missile crisis. Many say a nuclear world war was only just averted.
Memories of this came flooding back recently when reports circulated that Russia plans to place military planes in Cuba, in response to controversial US plans for a missile defence shield in Europe.
Washington will not miss the point that Medvedev has gone to Cuba from Venezuela, whose president does not hide his anti-US sentiment.