You probably didn’t know the U.S. government has formally ruled that Cuban kids in sailing dinghies are “detrimental to U.S. foreign policy interests.” And I don’t mean a gang of young Scarfaces sailing across the Florida Straits to terrorize the good folks of Florida. Nope. These kids just want to learn how to race little sailboats inside Cuba’s territorial waters.
The guy who wanted to deliver Optimist prams to Cuba is Bruce Kessler. He’s a former Formula One racer who went on to a career in Hollywood, directing baby boomer faves such as “The Monkees” and “The Flying Nun.” In retirement, Kessler enjoyed a third round of fame as a power cruiser and circumnavigator, but Type-A personalities never really retire.
To keep his directorial energies in harness, Kessler organized FUBAR, a biannual powerboat rally from California to La Paz in the southernmost region of Mexico’s Baja Peninsula. FUBAR (of course) stands for Fleet Underway to Baja Rally. Besides providing the buddy-boating structure to get a gang of powerboaters down the 700-mile Baja peninsula, FUBAR benefits the Newport Harbor Yacht Club’s youth sailing program.

So when Kessler conceived of CUBAR, he innocently figured that he would extend the franchise to benefit the youth sailing program operated by the Hemingway International Yacht Club in Havana, which I jokingly call the world’s only Communist yacht club. (It’s also the only yacht club to which I have ever belonged.)
In Kessler’s mind, a mighty fleet of trawlers would arrive at Marina Hemingway, each with an Opti lashed to the foredeck. PassageMaker magazine (motto: The Power Cruising Authority) would be CUBAR’s official media partner. A year ago this month, Kessler and PassageMaker editor-in-chief John Wooldridge visited Havana with me as a guide of sorts. We went by charter aircraft from Miami, not by boat.
But is he rich?
Jose Escrich, commodore of the Hemingway International Yacht Club, welcomed us and applauded the idea of a CUBAR rally, but he was skeptical. This was not Escrich’s first rodeo. In recent years he had seen the Sarasota Yacht Club fail to get permission to revive the 70-year-old tradition of its Sarasota to Havana Regatta, even though sporting events — like humanitarian efforts — are supposed exceptions to the U.S. travel ban.
At one point the commodore pulled me aside and asked me, “This man Kessler, is he rich?”
“I would say so. He has an expensive yacht. He was a famous Hollywood director. He directed ‘The Monkees.’ ”
“Los Monos” didn’t seem to register with Escrich, who probably didn’t get much exposure to 1960s American TV.
“Do you think he has any chance of getting Washington’s approval?” Escrich asked.
“I’d say his chances are about 10 percent, but Kessler is a determined guy and used to getting his way. If he can do it, that would be great.”
“Agreed,” the commodore said. Escrich sees a lot of dreamers across his desk, and I guess he was trying to gauge whether Kessler had the throw-weight to justify his time. Besides the yacht club, Escrich is busy administering the majority of Cuba’s marine infrastructure.
My own pessimism was based on experience. In 2005, I was denied permission to make a reporting trip to Cuba on my own boat. Condi Rice vetoed my application because my trip — and here’s that phrase again — would be “detrimental to U.S. foreign policy interests.”
Being a career journalist is the paramount exception to the U.S. travel ban, journalism being the only profession specifically protected by the Constitution. Yet even that was not enough for permission to “export” my boat to Cuba.
The rules
In a nutshell, here’s how it works. Under the terms of our Cuba embargo, the U.S. Treasury Department regulates which U.S. citizens may travel to Cuba —Treasury is in charge of people. Meanwhile, the conveyances to Cuba — the craft — are regulated by the U.S. Commerce Department. But wait, there’s more. Every applicant to the Commerce Department must be vetted by the Pentagon, the State Department and (don’t ask me why) the Energy Department.
As far as I know, State has vetoed every single application for a recreational boat that has ever been filed. It only approves applications for vessels 100 meters or greater, the ships that regularly call on Havana with shipments of beans and other American agricultural products (another strange wrinkle in the “embargo”).
Although the Obama administration has loosened the rules allowing whole classes of people to travel freely to Cuba — Cuban Americans, for example, and anyone wealthy enough to afford an organized culturally based tour — it has left in place Bush-era policies directed at U.S. boaters, a crackdown that began in 2004.
Ultimately, CUBAR organizers scaled down their proposal to just a handful of boats, hoping a small project was more likely to be sanctioned. CUBAR was supposed to sail later this month, but as is usual in these cases, the bureaucrats let the clock run, then announced that they would be issuing a denial.
“After reviewing your applications to permanently export five sailing dinghies to the Hemingway International Youth (sic) Club and to export the powerboats necessary to transport these dinghies on temporary sojourn, the Department of Commerce, in consultation with the Departments of State and Defense, concluded that your proposed transactions would be detrimental to U.S. foreign policy interests.”
Enter Jay-Z
The CUBAR denial went unheralded in the news media, but events conspired to shed light on our crazy Cuba policy, anyway. Hip-hop artist Jay-Z and his bride, Beyonce, had just returned from a trip to Havana, which (as it turned out) had been sanctioned by Treasury. Sanctioned or not, the trip got a rise from the Washington politicians responsible for keeping the travel ban in place, mouthpieces for a tiny but influential group of aging Castro haters that dictate U.S. Cuba policy.
Florida U.S. Sen. Marco Rubio was one. “U.S. law clearly bans tourism to Cuba by American citizens because it provides money to a cruel, repressive and murderous regime.”
The ever-predictable Florida U.S. Rep. Ileana Ros-Lehtinen also chimed in. “If the tourist activities undertaken by Beyonce and Jay-Z in Cuba are classified as an educational exchange trip, then it is clear that the Obama administration is not serious about denying the Castro regime an economic lifeline that U.S. tourism will extend to it,” she said.
Jay-Z responded with what I guess you would call a song. From “Open Letter”:
“Politicians never did s**t for me except lie to me, distort history. … They wanna give me jail time and a fine. Fine, let me commit a real crime.”
Well said, Mr. Jay-Z. You nailed it. U.S. foreign policy toward Cuba is FUBAR in the original sense of the acronym, and that’s why Kessler’s idea for a friendship fleet was probably “Mission Impossible” from the start.
Yep, that’s another show he directed.