Trump’s Biggest Cuba Deal


Cargo unloading at Mariel, Cuba. Photo: Dennis Arce López

Sue Ashdown

Back in the early years of the publicly available internet I used to spend a lot of time fighting telecom companies. Starting at my own state capitol and then moving on to Washington DC, I spent so much time at the FCC that I might have qualified for a rapid entry pass, if there were such a thing. This was back when net neutrality meant something besides giant oligopolies fighting amongst themselves to create the ultimate walled garden. The thousands of small entrepreneurs who first brought Americans online were the first casualty of Washington’s policy neglect and indifference in that era and it is still painful for me to contemplate their losses.

So pardon me if I’m not terribly moved by the enthusiasm in certain Washington circles for Cuban entrepreneurs as the demonstrable fruit of Obama’s policies to “empower” Cubans and bring about “democratic change.” Not only did small business licensing in Cuba predate the Obama/Castro opening, it seems to me that empowerment and democratic change begin at home, and I’ve seen that movie before.

The current argument that Cuba’s entrepreneurs will be devastated if Trump restricts travel to Cuba as urged by Marco Rubio and friends feels to me like nothing so much as an interfamilial squabble that has little to do with Cuba and everything to do with Miami.

On the one side are the new Miami companies who have reaped millions carting Americans to Cuba on paint by numbers tours, with stops and deliveries made to a specially selected handful of small Cuban businesses and experts in order to satisfy US regulations and policy goals.

On the other is the Miami old guard who also made a fortune over the years prior to the “opening,” charging $500 a head for airfares between Havana and Miami, producing unfunny TV Marti sketches that aired nowhere, and shopping at Costco for cashmere sweaters and Godiva chocolates to send to their Cuban “dissidents” on the dole. That monopoly slipped away under Obama, seized by the new guard, laser-focused on the entrepreneur micro-beachhead.

Don’t get me wrong. I would hate for travel to be restricted again. I have an 11 year old son in Cuba and a 91 year old father in delicate health in the US. Why must I contemplate choosing between the two? If I can go to North Korea, or Saudi Arabia for that matter, as many times as I can afford a visa and a ticket, why not Cuba? On the other hand, it’s not the end of the world. We’ll survive.

The real tragedy is elsewhere, in the enormous opportunity that President Trump seems certainly poised to lose.

Obama’s opening to Cuba, for better or worse, was contained in a package meant to satisfy the State Department’s foreign policy goals first and foremost. The problem with that approach is that if we confine and shackle our entire Cuba trade policy to small entrepreneurs because they make such a convenient political wedge, while other countries face no such restrictions and are doing the real grownup business of major imports, exports and production with Cuba, how long will it take for the US to catch up? Forever, basically.

Instead of following old Miami’s recommendations and turning back the clock again, President Trump is facing nothing less than a once in a lifetime chance to do something far more substantial and meaningful than Obama ever attempted. He could easily trump Obama – pun intended – the opportunity is ripe for the taking.

Standing shoulder to shoulder with his fellow Republicans in Congress, he could leave behind the pretense of worshipping at the altar of small business that no-one really believes in and go for the big play, the one that will pay immediate and significant dividends.

Working together with Congress he could finally overturn the embargo that has long hobbled the most substantial players in the US business community, gaining a much needed, easy and popular legislative victory in the process. Two birds with one stone.  Three, if you count the ensuing foreign trade victory against less-geographically blessed competitors. Four if you count a continued neutralization of one anti-US banner in Latin America.  Win win win win.  Granted, this requires recognition that the Florida congressional delegation’s bark is far worse than its bite, and the understanding that the bite will be even more toothless by 2020.

The moment is now, or never. It would be the Very Biggest Deal. Huge, really. What a shame that the odds are against it.



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