The Obama Administration announced yesterday that the President will make an historic visit to Cuba next month. While I advise Mr. Obama to go dancing and enjoy some daiquiris at El Floridita, he’ll likely spend most of his time bogged down in tense negotiations over ending the embargo and officially opening Cuba to US commercial tourism and investment.

If it sounds like a rubber-stamp done deal, think again. Much remains unresolved and there’s no guarantee Castro and Obama will reach a consensus. Here are three ways this deal could still go south:

1. Private property claims

After assuming power in 1959, Cuban Communists immediately began seizing assets, particularly those belonging to dictator Fulgencio Batista’s fellow elites and foreign corporations. Many Cubans lost property and businesses before fleeing to the United States.

Now that the countries are repairing relations, those Cubans and their descendants want their assets returned or, at the very least, to be fairly compensated for their losses.

So far, Raul Castro has showed no signs of wavering from his brother’s hardline stance against reparations. Is there any hope for resolution or will private property claims doom the Cuba deal? From the NY Times:

A State Department spokesman, who spoke on the condition of anonymity in keeping with department policy, said officials in the United States and their Cuban counterparts had touched on the topic during aviation talks. The department is negotiating with the Cubans over compensation for confiscated properties, but the cases of people who were not American citizens at the time of the confiscations were not included in those talks.

Read into the statement however you want, but it sounds like the two nations have agreed on a resolution framework but that not all claims will get settled.

2. Trade normalization

Perhaps looming even larger than private property claims is the issue of trade normalization. Many government-owned companies in Cuba are under US indictment (for why, see above) and, therefore, cannot operate on US soil without fear of arrest or asset seizure. Additionally, Cuba and the US have no existing trade and Cuba is not part of the US-led Caribbean Basin Initiative.

For example, something lost in the hoopla surrounding this week’s aviation agreement is the fact that Cuba’s nationalized Cubana de Aviación airline won’t be able to fly to the US; only US airlines will fly to Cuba. Why?

…negotiators were clear with Havana that the Obama administration would not be able to stop their planes from being seized by people who have successfully sued the Cuban government in American courts.

How long can Cuba expect to have their equal trade rights sidelined? It’s a very sticky situation that will likely take into another president’s administration to even begin to unravel.

3. Political prisoners and fugitive extradition

Another sticking point yet to be addressed is what the two countries will do with their remaining political prisoners as well as the extradition of wanted fugitives. Dozens of American fugitives — including convicted murderers and hijackers — remained holed up in Cuba. Will the US force Cuba to extradite at least a few as a symbolic gesture?

The interesting catch here is that a US-Cuba extradition treaty from the 1920s exists, but both countries have largely ignored it. So, it’ll take more than just a vocal pledge to extradite.

Major negotiations remain on the path to normalization, but I’m optimistic the Obama Administration will clear the major hurdles; and very soon we’ll all be packing our bags for Cuba no different than we do for Jamaica. Uh, oh.

h/t:
CNN
NY Times