The re-establishment of regularly-scheduled non-stop commercial flights from the United States to Havana, Cuba, and return provide a highly-visible and an additional measure of normalcy in an anything-but-normal bilateral commercial, economic and political relationship.
In some respects, the flights are Potemkinesque- camouflaging the real and imagined issues that each country has with the other; but doing so in a picturesque manner… with the expectation that the one-dimensional will become three-dimensional.
The commencement of the flights will increase already unrelenting pressures upon the hospitality infrastructure of Cuba, particularly airports, ground transportation and hotels- which will continue to unnaturally restrict capacity and create reasons for travelers to select alternative destinations in the short-to-medium term.
Individuals associated with the President-Elect, both officially and unofficially, will not be enthusiastic about the resumption of the flights; they will view each flight as a satchel of United States currency traveling on a one-way journey to Cuba- with no meaningful measurable return other than to perpetuate abhorrent commercial, economic and political systems. And, most significantly, they will view the passengers on those flights as tourists- in violation of United States law, not policy or regulation, per provisions of the Trade Sanctions Reform and export Enhancement Act (TSREEA) of 2000 which created twelve (12) categories of authorized travelers; with tourism specifically prohibited.
Members of the United States Congress will share their expectation that a Trump Administration will eliminate or reduce the flights.
Reasonable to expect that the Trump Administration will increase enforcement by the Office of Foreign Assets Control (OFAC) of the United States Department of the Treasury to ensure that only TSREEA-authorized travelers are using the flights- and the OFAC will have a position that both the “letter” and the “spirit” of the categories will be enforced. The result would be a decrease in the number of passengers using the flights.
The President-Elect, his transition team, and supporters may initiate a discussion relating to the implementation of Title III of the Libertad Act of 1996. This provision enables those with assets expropriated by the government of the Republic of Cuba to bring lawsuits in United States Federal Courts. The Libertad Act requires the president to either enable or suspend the provision every six months; and Presidents Clinton, Bush and Obama have done so. The next decision upon a suspension must be by the end of January 2017; President Obama could suspend Title III before he departs office on 20 January 2017, thus providing at least six months of reprieve- and provide an opportunity for United States companies to advocate for continue suspensions.
The President-Elect, his transition team, and supporters may view creating uncertainty now about the statue of Title III as an effective means of destabilizing the interest by the United States business community toward Cuba; and it would be successful.
For example, there are individuals who maintain they have actionable claims relating to the Jose Marti International Airport (HAV) in Havana, Cuba, and at the Port in Santiago de Cuba. In the case of HAV, United States-based air carriers and those from other countries could find their assets attached if they do not avoid Cuba. In the case of the port, passenger cruise ships and cargo ships might avoid docking and unloading for fear of expensive and enduring legal proceedings.
If President Obama leaves the decision to suspend Title III to President Trump in January 2017, I would expect that there would be a suspension. However, there would likely be an aggressive signing statement designed to create uncertainty relating to what will happen six months from January 2017.