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Trump has Four Choices on Cuba

Candidates Donald Trump and Mike Pence promised Cuban-Americans they would roll back President Barack Obama’s initiatives normalizing relations with Cuba. That would undoubtedly include rolling back policies that now allow U.S. citizens to visit Cuba by boat.

“All of the concessions Barack Obama has granted the Castro regime were done through executive order, which means the next president can reverse them, and that I will do unless the Castro regime meets our demands,” Trump said at a campaign stop in September. “Not my demands. Our demands.”

Let me go out on a limb here and opine that Trump’s demands will meet the same steely resolve that the Castro brothers demonstrated in the face of demands from Kennedy, Johnson, Nixon, Ford, Carter, Reagan, Bush 1, Clinton and Bush 2. My sense is that ordinary Cubans living in Cuba would be extremely disappointed, but they would mostly support their government against what they would perceive as bullying.

A pair of U.S.-flagged sailboats race past El Morro castle at the entrance to Havana Harbor in 2013, two years before the Obama Administration made it legal for them to enter Cuban waters.

A pair of U.S.-flagged sailboats race past El Morro castle at the entrance to Havana Harbor in 2013, two years before the Obama Administration made it legal for them to enter Cuban waters.

Maybe the Trump/Pence vow was just an act of political smoke-blowing. Business interests are lining up to lobby in favor of maintaining diplomatic relations and existing travel policies. Says USA Today:

That list includes most major airlines, which have started regularly scheduled commercial flights to Cuba, and Carnival Corp., which is already running a regular Cuba cruise. It will include Starwood Hotels and Resorts, which is operating three Cuban hotels, and Airbnb, which is being used by more than 8,000 Cubans to rent their rooms to travelers.

There are tech giants, such as Google and Cisco, trying to develop Cuba's bare-bones telecommunications infrastructure, cellphone giants offering roaming services, and banks starting to offer U.S.-issued credit and debit card services.

Add to the list The Moorings, which has scheduled a crewed charter program on Cuba’s north coast for the spring and has plans to establish a bareboat base on the south coast. The uncertainty brought on by Trump victorious has Moorings executives worried.

There is a tendency among Cuba enthusiasts in the marine industry to be optimistically selective in their hearing. I think back to a former boss of mine who insisted that George W. Bush, whose administration cracked down on boating travel to Cuba, was actually going to end the travel ban. He got that notion while attending a Bush rally in Florida. Bush said he’d open Cuba up to Americans, all right — after he had run the Castros off the island. My boss apparently heard the first part, not the impossible qualifier.

Electoral math may well outweigh capitalistic considerations in the mind of Trump, who might already be thinking of a second term. Florida was ground zero for Trump’s surprise victory, and I would argue it was the Cuban vote that delivered Florida. More than 50 percent of the Cuban-American electorate voted for Trump. Had they voted for Trump at the same rate as Latinos at large — 26 percent — Hillary Clinton would likely have taken Florida. Subtracting Florida’s 29 Electoral College votes from Trump’s column and adding them to Clinton’s would have created a 261-261 tie and a national debacle.

Having said that, maybe President Trump will scout out some middle ground. He has four options.

1. Continue to advance the Obama agenda toward Cuba, highly unlikely given his debt to hard-line Cubans in Florida.

2. Do nothing, letting Obama’s initiative stand.

3. Roll back some or all of the initiative, returning us to the Bush status quo ante.

4. Leave Obama’s policies in place, but aggressively enforce the regulations that allow Americans to visit and do business in Cuba under so-called general licenses.

This could prove nettlesome for U.S. citizens who have visited Cuba by air and by sea and were blasé toward the regs, and there have been many, including some organized boating rallies.

The problem lies in the Treasury Department’s requirements that Americans engage in “people-to-people” educational activities, the most common form ofgeneral license used by travelers by air or boat. These activities, say the regs, must constitute a full-time schedule.

U.S. citizens may take their own boat to Cuba and engage in self-directed educational activities. No problem. But if they go under the auspices of an organization, it’s up to the organization to ensure that participants adhere to that pesky “full-time schedule.”​ It’s not enough to “develop an itinerary,” then let the folks go off on their own.

Here’s what lawyer Greg Singer, who follows Cuba travel issues for the admiralty Lochner Law Firm of Annapolis, says:

My read since March is that if you're doing P2P under the auspices of the organization you can't have people just doing their own thing (and therefore, if people are just doing their own thing, the organization should not profess that it is making the thing "legal"). I think that if a rally were to charge participants strictly for U.S.-based things (parties, inspections, advice, etc.) and basically set them loose in Cuba (with the understanding that the rally was not providing legal cover), that would be OK.

But if you're selling a Cuba rally and you're telling folks that your organization is covering the legal aspect, I don't see any way that they can qualify by the participants doing their own thing. Unless they just want to ignore the rules, which is fine, but in that case why bother joining a rally in the first place when you can ignore the rules just as easily (nay, easier) as an individual?

Treasury’s Office of Foreign Assets Control is in charge of enforcing the regulations regarding travel to Cuba. And it has the ability to go back five years and ask people who have traveled to Cuba to provide records that prove they abided by, say, the full-time schedule. Failure to prove your case could result in fines, criminal penalties and possibly forfeiture of assets. This hasn’t happened to any ordinary citizens under Obama, but OFAC has reached back years to punish corporate embargo violators. In theory, Trump could direct OFAC to reach back and roust some of those “rich yacht people” who visited Cuba in 2016 and make examples of them to appease his Cuban-American supporters.

Trump does not take office until Jan. 20, and it would probably take months to rewrite OFAC regulations backward, if that’s the route he chooses. This means we could see new regs in April, May or June, which happen to be the best months to make a crossing from Florida to Havana. If stricter and retroactive enforcement is part of the plan, we could see that happen earlier.

Let me offer some advice for anyone considering participating in a Cuba rally. If the organizers are promising legality and the price is less than $1,000 per person for a week, something ain’t right. You are probably not going to get that “full-time schedule” of educational and cultural programs. A red flag is a rally that collects most of its money on a per-boat basis, not per person. Boats going to Cuba usually have two people aboard, but they could have four, five, six or more. Problem is, all of the shoreside activities that comprise a legal program charge per person.

One more thing to consider, and this comes from a well-placed individual in the marine insurance industry. In the unlikely event that your unlucky stars align, and OFAC identifies your rally as having broken the rules at the same time you file an insurance claim for a loss in Cuban waters, that claim would be denied. Why? Because failure to comply meant that you were “trading with the enemy” under U.S. law.

One guy planning a rally recently accused me of overthinking things. To him, I would say that parsing risk is what any good sailor does before undertaking an ocean passage. Identify the risks, then decide. Heck, I know an American in Havana — a delightful character — who has taken boats to Cuba more than 25 times illegally without suffering any consequences … so far. He also smokes cigarettes and refuses to wear seatbelts.