Alfonso Fanjul fled Cuba as a young man, leaving behind his family's mansions and vast sugar-cane fields as they were being wrested away by the communist Castro regime.
In exile in the United States, he built an even larger sugar empire, amassing one of North America's great fortunes and befriending members of Congress and presidents who benefited from his largess. The sting of his family's forced departure from Cuba led him to become one of the principal funders of the U.S. anti-Castro movement.
Now, contrary to what almost anyone could have imagined, the 76-year-old Fanjul has begun to reassess old grievances and tentatively eye Cuba as a place for him and other U.S. businessmen to expand their enterprises. Quietly, without fanfare, Fanjul has started visiting the island of his birth and having conversations with top Cuban officials.
"If there is some way the family flag could be taken back to Cuba, then I am happy to do that," Fanjul said in a rare interview, publicly discussing his recent visits to the island for the first time.
Fanjul's about-face is a startling development for the exile network that has held a grip on the politics of U.S.-Cuba relations for decades and has played an outsize role in presidential campaigns. His trips place him at the vanguard of a group of ultra-wealthy U.S. investors with roots on the island whose economic interests and political clout are pushing the two countries toward a thaw in their half-century standoff.
Fanjul, in the interview, said repeatedly that his primary motivation in visiting Cuba has been a desire to "reunite the Cuban family," referring broadly to the Cuban diaspora and those who remain on the island. Business considerations could be explored only if there are political and diplomatic advances, he said.
"The Fanjul family was in Cuba for 150 years, and, yes, at the end of the day, I'd like to see our family back in Cuba, where we started. . . . But it has to be under the right circumstances," said Fanjul, who is best known by his nickname, "Alfy." "One day we hope that the United States and Cuba would find a way so the whole Cuban community could be able to live and work together."
Fanjul, who lives in Palm Beach and whose family holdings include Domino Sugar and refineries across the United States, Latin America and Europe, has managed to maintain a remarkably low profile for a politically connected tycoon. His access to the highest levels of power was evident during the Monica Lewinsky scandal of the 1990s, when the special prosecutor's report noted that President Bill Clinton received a call from Fanjul during a private Oval Office moment with the intern.
Last week, the Fanjul family's influence over policymakers was on display when the U.S. House passed a farm bill that would cut subsidies to many agricultural products while leaving unscathed the controversial, taxpayer-backed program that protects sugar profits.
Fanjul visited Cuba in April 2012 and again in February 2013 as part of a delegation licensed through the Brookings Institution, the Washington think tank that has produced recent papers criticizing U.S. policy and calling on the Obama administration to further loosen sanctions. In Havana, he lingered with tears in his eyes at his family's colonial-era manse, now a museum, with its elegant columns, lush inner courtyard, sparkling chandeliers and grand staircase.
He was so taken by the nostalgia and excitement of returning to the familiar streets of his youth, a travel companion recalled, that Fanjul enthusiastically chatted up random people of all ages as he walked around. He also met with Cuba's foreign minister and toured state-run farms and a sugar mill with Cuban agricultural officials.
After returning from his first trip, Fanjul met with his good friend, then-Secretary of State Hillary Rodham Clinton, to express his changing views on Cuba. In November, Fanjul once again discussed his evolving mind-set with Clinton and her husband at a Clinton Foundation fundraiser in the Miami home of Cuban American businessman Paul Cejas, a former U.S. ambassador to Belgium.
Many embargo supporters say U.S. policy should change only when certain conditions are met, such as regime change or political reforms. Fanjul, however, said he prefers not to answer the question of whether he would require the fall of the Castro government or an end to communism before doing business in Cuba — saying that he respects existing U.S. law.
"Right now there's no way for us to consider investing in Cuba. How can you work a deal if you're not legally allowed to do it?" he said.
"Now, would we consider an investment at some later date?" continued Fanjul, a permanent U.S. resident who maintains Spanish citizenship. "If there's an arrangement within Cuba and the United States, and legally it can be done and there's a proper framework set up and in place, then we will look at that possibility. We have an open mind."
He said the Cuban government, which has business deals with companies from countries such as Canada and Spain, would have to change its economic structure to make it easier and safer for outside companies to make money.
"Cuba has to presumably satisfy the requirements that investors need, which are primarily a return on investment and security of the investment, so they feel comfortable with what they're doing," he said. "I personally would look at that in the same framework as any investor would."
The logistical, political and legal complexities involved in any potential expansion of U.S.-based businesses onto Cuban soil are staggering. Fanjul's willingness to hold meetings with the Castro government puts him on a potential collision course with Senate Foreign Relations Committee Chairman Robert Menendez, D-N.J., a Cuban American whose campaigns have been supported by Fanjul but who is an unwavering advocate for the embargo and has the power to thwart any attempts to lift it.
Trickier still would be the impact on presidential politics, with Florida's Cuban American electorate still a significant factor in the battle for that state's crucial electoral college votes.
Already, there have been signs that younger Cuban Americans, particularly those born in the United States, are moving away from the hard-line views of their parents and grandparents. Now, as Fanjul's recent gestures show, even some of the most entrenched exiles are evolving, and politicians accustomed to embracing the Cuba trade embargo in their pursuit of Florida's large Cuban American electorate will have to calibrate the risks and rewards of evolving along with them.
Hillary Clinton, the putative Democratic front-runner for president if she chooses to run in 2016, has spoken out in favor of the Obama administration's actions relaxing restrictions on family travel and cash flow to the island. Yet she, like many politicians in both parties, has repeatedly expressed support for continued sanctions. She is close with several key players, besides Fanjul, who have stated an openness to more engagement with Cuba.
The issue could prove thornier for Republicans, such as Sen. Marco Rubio, R-Fla., a Cuban American widely seen as a possible 2016 presidential candidate. A staunch supporter of sanctions who blasted President Barack Obama's loosening of some restrictions as an "enrichment of a Cuban regime that routinely violates the basic human rights and dignity of its people," Rubio has cited the Fanjul family as a crucial source of campaign funds and political connections.
Fanjul said repeatedly during multiple interviews that "this is a highly sensitive issue." He said he needed to "stay at a high altitude" in discussing potential changes in U.S. policies toward Cuba because of the political challenges involved. "What I say can be taken in the wrong context," he said.
"Do I have a soft spot in my heart? Yes, that's my country. My interest is finding a way to unite the Cuban family," he said. "When you talk with people and hear them, it humanizes. Talking is the first step."