Historian Max Paul Friedman has a tremendous op-ed about the lessons Barack Obama could learn from Calvin Collidge's visit to Cuba in 1928 (the last time a U.S. president went to Cuba). He discusses the politics of the time and the symbolism involved. In particular, he notes the timing.
But when Coolidge’s diplomats returned to Washington, they began to mull the extent of Latin American resentment of heavy-handed U.S. policies, and proposed a new approach that would end unilateral military intervention in the region. Five years later, that proposal flowered into Franklin Roosevelt’s Good Neighbor Policy, which brought the most harmonious era of inter-American relations in history. Machado was overthrown.
To sum it up, the U.S. President visited Cuba when it was ruled by a dictator and gave a speech that exaggerated the degree of freedom on the island. But he was received warmly by the Cuban people, and his visit was a significant step on the path to improved relations with Cuba and the rest of the hemisphere.
As the saying goes, history doesn’t repeat itself, but sometimes it rhymes.
This is a great observation. It also underlines the fact that change isn't instant. Obama gets a lot of criticism because things aren't happening fast. Back in 2014, Alan McPherson published an article about how Herbert Hoover deserved more credit than he receives for the genesis of the Good Neighbor Policy. Coolidge in fact went to Cuba in the last year of his presidency, then handed things over to Hoover. The shift in policy was slow, but it stuck. At least until the Cold War started, but that's another story.