Obama’s historic trip to Cuba: a brief guide to what it means and why it matters

On Monday morning, we heard something many thought impossible just two years ago: a Cuban government band playing the American national anthem.

President Barack Obama had arrived in Cuba the night before, the first official visit of a US president since Calvin Coolidge in 1928. In many ways, it represents the culmination of Obama's approach to the island: a concerted effort to break down the decades-old US embargo and move toward normal relations.

Here's a brief guide, then, to Obama's Cuba trip: what he's doing and why it matters.

Obama's Cuba trip is a victory lap

Vox's Libby Nelson has a good rundown of Obama's agenda in Cuba, which includes:

• A tour of Old Havana
• A meeting with Cardinal Jaime Ortega, the Cuban clergyman who played a backchannel role in Obama's negotiations with the Castro government
• Visiting an art museum
• Taking in a baseball game with Cuban leader Raúl Castro. The Tampa Bay Devil Rays will play Cuba's national team.
• Delivering a televised speech to the Cuban people

If this sounds like the normal stuff of a state visit, that's because it is. But a "normal" meeting, in the long run of US-Cuba relations, is really stunning.

Obama still hasn't ended the American embargo on Cuba; only Congress can do that. Rather, he has relaxed specific trade barriers. What he has changed, successfully, is the American diplomatic approach that underpinned that embargo: treating Cuba as a pariah state, much like North Korea or Iran.

The new strategy is to work with Cuba rather than against it: to attempt to improve life in the country through negotiations and commercial ties rather than attempting to topple the communist government through isolation and economic pressure.

"His policy toward the island is, without a doubt, his boldest hemispheric initiative," Susan Segal, the president and CEO of the Americas Society and Council of the Americas, writes for CNN.

"It chips away at a more than half-century-old embargo policy that has hurt ordinary Cubans, put US commercial interests at a disadvantage compared to those of other countries, and poisoned the US relationship with the rest of the continent."

This has already had some effect. The number of Americans visiting Cuba increased by 77 percent in 2015, a figure that's only likely to increase further as US airlines open up direct flights to Cuba.

"The arrival of so many visitors … represented a boon for all manner of Cuban-owned small businesses in the island’s services-focused cuentapropista (or self-employment) sector," Michael Bustamante, a PhD student at Yale who studies Cuba, writes in Foreign Affairs.

"On the international business front, meanwhile, some US companies, such as the apartment-sharing service Airbnb, are now operating on the island; many more are looking for opportunities or are in talks with Cuban officials," Bustamante continues.

Obama's trip to Cuba is a way of building on these accomplishments. If the US and Cuba do normal activities like state visits, then this signals to the populations of both countries that the era of unremitting hostility is ending.

"In some respects, the US-Cuban rapprochement is still tenuous, and Obama’s visit is necessary to give a boost to a process plagued by fits and starts," Bustamante writes.

But it's also the start of a new, complicated policy

Still, Obama has a long way to go if he wants to continue relaxing the decades of US-Cuba hostility.

That includes, for example, easing bureaucratic hurdles that make it difficult to actually deepen business ties.

There's also the question of how the US will deal with Cuba's terrible human rights record. My colleague Max Fisher explains some of that record:

According to Freedom House, Cuba has the most restrictive press censorship in the Western Hemisphere and is the only country rated "not free" in the Americas. All official media is owned by the state and controlled by the government. Dissident bloggers are regularly arrested. According to Amnesty International, protestors are regularly arrested and detained without trial. The Foundation for Human Rights in Cuba says there were over 6,000 arbitrary detentions of human rights activists in 2013.

In the past, the US has tried to pressure Cuba into reform. Clearly that hasn't worked. On this trip, Obama is scheduled to meet with Cuban dissidents on Tuesday. It would be surprising if he didn't mention something, at least obliquely, during his televised address to the Cuban people.

Judging from some early Obama comments, it looks like he's trying to debut something along the lines of the US approach to China. The US certainly makes an issue of Chinese human rights violations, but it is unwilling to seriously threaten trade ties over domestic repression.

The ultimate hope is that sustained diplomatic engagement and liberalized trade will encourage ordinary Chinese citizens to engage in political activism, leading them (rather than the US) to create the pressure necessary to change their government.

"We still have some work to do," Obama told ABC's David Muir in a Sunday interview in Havana. "I think it is very important for the United States not to view ourselves as the agents of change here, but rather to encourage and facilitate Cubans themselves to bring about changes. … We want to make sure that whatever changes come about are empowering Cubans."

Obama is a good messenger for human rights in Cuba: About 80 percent of Cubans approve of his job performance, likely as a result of widespread support for the US opening. In fact, observers say that Cubans will be let down if Obama doesn't highlight repression.

"If Obama focuses too much on corporate signing ceremonies rather than Cubans’ desires for greater political and economic openness domestically, he will also be seen as having let the island’s authorities off the hook," Bustamante argues.

But Obama has to be careful. Cubans remember the long history of malign American interference in their country's life, so overweening lectures could end up backfiring. The trick is to highlight human rights in a way that pays respect to the issue's importance without coming across as arrogant or paternalistic.

"One of the most important gestures Obama can make is to acknowledge that Cuban society is complex and that its problems do not lend themselves to quick, imported fixes," Bustamante concludes. "Cubans themselves, ultimately, and only Cubans themselves, must be the principal agents of their economic and political futures."