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by Jared Carter, Esq. Vermont and Cuba: An Unlikely Cultural and Legal Connection Just before the turn of the century, in


1898, Teddy Roosevelt and his band of “Rough Riders” galloped up a small hill in eastern Cuba and into the history books. As the story goes, Roosevelt’s troops played a key role in throwing off the chains of Spanish colonialism and offering Cuba a chance at economic sovereignty and inde- pendent nationhood. Of course, all stories have two sides and the truth is often much more complex than simple anecdotes in- dicate. To hear a Cuban tell it, the story of Roosevelt’s “Rough Riders” in Cuba is based less on altruistic ideals than politi- cal ambitions. If you ask a Cuban, they will point to the fact that even after Cuba had won independence from Spain, U.S. diplo- mats refused to attend the political cere- monies that ensued. Instead, Cubans will point to the legal machinations of the U.S. Congress and such initiatives as the Platt Amendment—an amendment to a 1901 military spending bill that granted Con- gress veto power over all acts of the Cu- ban legislature and the perpetual lease of the Guantanamo Bay Naval Base for only $4,800 per year (to this day, that annual lease payment has remained the same). Whatever the story, the United States and Cuba have had a tortuous relation- ship. For the first half of the twentieth cen- tury Cuba was the playground of Ameri- can tourists. During the prohibition era, millions of Americans traveled the nine- ty miles from Key West to Havana to im- bibe the rum and carouse in the city’s casi- nos. U.S. soldiers dressed in sharp navy uni- forms were a common sight as they plied Havana’s cobblestone streets and colonial squares during their leave time from the military bases located around the island. Colorful mafia figures in expensive linen suits are said to have been frequent visi- tors as they controlled many of the liquor and gambling businesses that were prev- alent in Havana at the time. This scene of mafia figures, rum, cigars, gambling, and debauchery came to a sudden end in 1959 when Fidel Castro and his band of bearded rebels stormed Havana and sent Fulgen- cia Batista, a U.S.-backed dictator, packing. After a short honeymoon period in which it appeared that Cuba and the U.S. would maintain their cozy relationship, things took a turn for the worse. Through a seri- ous of Cold War era incidents, Cuba quick- ly became public enemy number one and by 1962, the now decades old Cuban Em- bargo was in place.


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Flash forward to 2012 and most people


are at least vaguely aware that it has been nearly fifty years since the United States first began enforcing an economic embargo on Cuba. For almost five decades, and elev- en presidents beginning with Eisenhower, all economic activities between Cuba and the United States have been carefully con- trolled and tightly restricted by the Office of Foreign Assets Control (OFAC), an en- forcement arm of the United States Trea- sury Department. From the Cuban Missile Crisis to the Bay of Pigs and the Guanta-


THE VERMONT BAR JOURNAL • WINTER 2012


namo Bay Prison, Cuba has occupied a unique place in the American psyche and in American jurisprudence. The record is rife with examples of U.S. companies (and pri- vate citizens) being fined or otherwise rep- rimanded by the Treasury Department for either doing business with, or travelling to, Cuba. Between 1961 and 2000 there have been varying levels of enforcement under a set of economic restrictions that are un- paralleled in the history of international re- lations. From complex banking regulations that prohibit banks from doing business in


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