During the late 1950s, that kind of trip would become politically impossible. Cuba became a focal point of U.S. foreign policy, a key element of a global political struggle with the Soviet Union.
Fidel Castro waged a guerilla war against Fulgencio Batista, the U.S.-backed dictator, from 1956 until the fall of the corrupt and brutal government in 1959.
Castro, who established a socialist government and allied himself with the Soviets, faced many decades of efforts by U.S. administrations to oust him. Many elite Cubans fled the country and moved to Florida where they became a powerful political force and pressured U.S. politicians to resist interaction with Cuba, arguing that this remained a central front in the Cold War.
Democrats were especially nervous given that many Cuban-Americans tended to vote Republican after a disastrous CIA operation in 1961, known as the Bay of Pigs, undertaken under President John F. Kennedy.
When he ran for president in 1992, Democrat Bill Clinton appealed
to Cuban-Americans in Florida by promising to be tougher with the Castro government. "I think this administration," he said of President George H.W. Bush, "has missed a big opportunity to put the hammer down on Fidel Castro and Cuba" by not pushing for the Cuban Democracy Act, which strengthened the U.S. embargo against Cuba.
Touch it and you die
For Americans over a certain age, the Obama trip is remarkable. For most of their lifetime, normalizing relations with Cuba was a third rail in American politics. Like cutting Social Security, touch it and you die. No president in either party gave serious thought to easing tensions with the Cubans, let alone visiting.
That was then, this is now. Obama has fully embraced opening relations with Cuba even though he condemns the human rights violations of the government. For younger Americans, this probably isn't a very big deal. Cuba is not a major issue anymore, and any lingering tensions are just relics of an older political era.
Obama, who did pretty well with the Cuban-American vote in 2012, is not fearful
of any serious political fallout from the trip, nor are the Democrats who are running for the nomination. Hillary Clinton supports him, as does Bernie Sanders who has already been to Cuba and is more sympathetic to the government, an issue that came up in the recent debate.
Opposition can still be fierce. Sen. Ted Cruz has strongly opposed these initiatives and is a staunch critic of any effort to work with Cuba. "You know today is a sad day in American history," Cruz said. "For decades leftists and Hollywood liberals have made the pilgrimage to Cuba to pay homage to Fidel Castro and Raul Castro. It's very chic, it's very chichi for leftists to celebrate vicious communist dictators." There are also some Democrats, including Sen. Robert Menendez of New Jersey, who have criticized Obama's moves.
But it is notable that the current GOP front-runner, Donald Trump, only said that he would insist on a better deal. John Kasich has said he would insist on greater changes in the government before normalizing relations but has been lukewarm in his criticism on this issue.
Republican Sen. Jeff Flake of Arizona, who is with Obama in Cuba, said the trip
"signals the beginning of a new era" and that "any Republican administration would be hard-pressed to reverse really any of this. This all feeds on itself."
What happened? How did standing tough against Cuba lose its potency on the campaign trail?
There has been a notable thawing of sentiment within the Cuban-American community toward opening economic relations with the Cubans and engaging, even if not accepting, the government.
The Wall Street Journal reported
that in Miami-Dade County, Cuban-American support for the embargo had fallen to 48% by 2014, down from 87% in 1991. Younger Cuban-Americas have been especially uncomfortable with the hard-line views of their elders.
There are even high-level Cuban business leaders who for the first time are openly supporting this kind of engagement and the President's trip. According to The Miami Herald, 10 prominent Cuban-American businessmen from Miami went to Cuba after Obama's announcement and returned convinced that stronger ties would be better for the nation.
In a letter published in the newspaper
, paid for by two Republicans who were part of the travel group, this cohort of business leaders said: "As fellow Cuban-Americans, let us recognize the progress that has been made on both sides of the 90-mile Florida Straits, albeit halting, in the right direction."
End of Cold War prompts changes
Foreign policy changes have also rendered the isolation of Cuba an outdated foreign policy position that no longer carries much weight. The Cold War, which shaped U.S. policy since World War II, gradually came to an end in the 1980s following a historic set of meetings between Ronald Reagan and Mikhail Gorbachev.
After the two leaders agreed on a major arms agreement in 1987, the Soviet Union eventually collapsed, leaving Cuba basically on its own. The nation lost its centrality in U.S. foreign policy as a result, even though antipathy toward normalizing relations remained strong. Then 9/11 shifted our focus to a different threat.
Much of our foreign policy debates revolve as much around issues that have symbolic power with the electorate as they do actual considerations of foreign policy. With foreign policy focused on terrorism, particularly in the Middle East, Cuba doesn't mean as much to voters. Although some conservatives have attempted to make connections between the Cuban government and Islamic terrorists the case has not been every effective.
With the new global economy and Internet age of communication, the notion of true isolation of Cuba until the regime changes its authoritarian ways makes much less sense.
And after so many decades of socialist rule, the argument that the embargo could produce change in Cuba's policies weakened. With corporate interests eager to establish a better presence on the island (Obama is being accompanied by a number of business titans) the supporters of isolation find less support.
The model of China has also offered a powerful counterpoint to supporters of the embargo. There, commercial ties with the United States have helped transform the country dramatically in social and economic terms even as older forms of political repression remain in place.
Starting in December 2014, the Obama administration decided it was worth taking any potential risk and changing the direction of policy.
With a look at the polls the President announced the re-establishment of diplomatic relations with Cuba and that the administration would ask Congress to end the U.S. embargo, though it remains in place. Obama's announcement broke the political ice, enabling other politicians to live with the realities of the new world and accept a status quo that was very different than before.
So Cuban politics ain't want they used to be, and the result is that the President has been freed up to make this political trip with minimal costs to his party politically. The bigger question is not so much about the implications for Obama as for those Republicans and Democrats such as Menendez still holding out for what increasingly looks like an outdated policy rather than joining the emerging consensus to help shape more coherent and effective approaches to handling Cuba today.