Barack Obama, our man in Havana?
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President Obama wants to be the first sitting president to visit Havana since Calvin Coolidge in 1928, and plans to go on March 21, a day after the Rolling Stones play there.

But the man who wants to make history by going to Cuba needs a lesson in Cuban history.

The opening to Cuba just over a year ago was out of a novel by Graham Greene, with hush-hush meetings, spies and shady characters, and even divine intervention by the Vatican. I welcomed it, as did many Cuban-Americans. Relations between my two countries have remained frozen since the Cold War, and a thaw is long overdue.

Obama's initial approach was a shrewd one. He agreed to remove Cuba from the terrorist watch list and open an embassy. But these changes were more symbolic than substantive. Cuba can't afford to provide sheets to patients in state-run hospitals, much less fund terrorists, and the U.S. Interests Section was an embassy in all but name. Real concessions, such as lifting the embargo, would come only if Cuba opened up its repressive society, which remains mired in the Soviet era.

Obama then dangled a delicious carrot to the geriatric Castro brothers, offering to visit the island if progress was made on human rights.

But the reverse is true. In fact, as reported by The Washington Post, in 2015 there were more than 8,616 documented political arrests in Cuba, as compared to 2,074 arrests in 2010 and 4,123 in 2011. Christian Solidarity Worldwide documented 2,300 violations of religious freedom compared to 220 in 2014. The Castros had released 53 political prisoners as a gesture in December 2014, but most of them have been re-arrested, and five have been given long-term prison sentences. And Cuba has yet to allow a visit by the International Committee of the Red Cross or U.N. human rights monsters, as it had promised.

In addition, Cubans are leaving the island in record numbers, often by way of Mexico. They fear the U.S. will end the "wet foot-dry foot" policy, but it also shows things are not getting better at home.

Then why is Obama going to Havana, other than scratching one more item from his rhymes- with-bucket list? Perhaps his pal Jay Z told him it would be "fun," as Obama flippantly claimed, or maybe he wants to visit Ernest Hemingway's house, like other American tourists, or have a photo op with Fidel en famille, like the star-struck Pope.

(According to the White House, Obama will only meet with Fidel's brother Raúl, and attend an exhibition game of the Tampa Rays against the Cuban national baseball team.)

Except there's another reason. Deputy National Security Advisor Ben Rhodes gave a clue when he said, "the guiding principle of our Cuba policy ... remains taking steps that will improve the lives of the Cuban people."

But throughout history, American efforts to improve the lives of the Cuban people, often well-meaning if rarely disinterested, have led to fiascos like the Bay of Pigs.

Rhodes notes that Obama's visit will be rather different than Silent Cal's trip to Havana in 1928, but there are alarming similarities. Coolidge went to prop up the corrupt, brutal regime of Gerardo Machado, who did more than anyone else to destroy the institutions of the Cuban republic. But it backfired, and Machado was thrown out in a gruesome revolt in 1933 in which bloodthirsty mobs roamed the streets of Havana and the dictator's henchmen were hung from streetlights. Hemingway was there, and he wrote about it in "To Have and Have Not."

Machado's successor was handpicked by the American ambassador, Sumner Welles. He was an obscure sergeant named Fulgencio Batista, who led a barracks revolt that ended Cuban democracy, effectively ruling until Castro swept into power in 1959.

Castro was another losing bet. Students of Cuban history know that toward the end of the revolution, he was backed by the U.S. Castro did not defeat Batista militarily, but holed up in the mountains, giving Trumpish interviews to fanboy reporters like Herbert Matthews of The New York Times. Batista threw in the towel only when the U.S. withdrew its support and stopped sending him guns and ammo.

Cubans have long memories. It was support for venal thugs like Machado and Batista, fueled by U.S. business interests, that spawned the virulent anti-Americanism that Castro was able to exploit when he turned the tables on the U.S. and declared himself to be a communist.

No-drama Obama has caused a ruckus by offering a carrot with no stick. If his visit enables the Castro brothers, who'll soon join Machado and Batista in the dustbin of history, then it will be deja vu all over again.

At best it's a gamble, but the U.S. lost big when it rolled the dice with Machado, Batista and Castro.

Rhodes said that Obama would meet with dissidents in Havana, but Secretary of State John KerryJohn Forbes KerryFeehery: Oprah Dem presidential bid unlikely Dem hopefuls flock to Iowa Change in Iran will only come from its people — not the United States MORE just canceled his warm-up trip, apparently due to disagreements over which ones he will meet, according to the Los Angeles Times. The spectacle of the U.S. haggling over this is deeply troubling, and creates a terrible precedent for future negotiations with the Cuban government.

Don't go to Cuba, Mr. President.

Estrada was born in Cuba and graduated from Harvard University before practicing law and founding HISPANIC Magazine. Based in Austin, he is currently the editor of LATINO Magazine and the author of the novel "Welcome to Havana, Señor Hemingway" and the nonfiction book "Havana: Autobiography of a City."