Raúl Castro estrecha la mano de Barack Obama

Educating the President: How Obama’s Cuba Policy Came Together

Educating the President: How Obama’s Cuba Policy Came Together

The Story Behind Obama's Cuba Trip

Raúl Castro estrecha la mano de Barack Obama
Raúl Castro estrecha la mano de Barack Obama

By David Adams @dadams7308

It all began with a chance encounter between two men with a bad habit.

Officially, Barack Obama's historic visit to Cuba on Sunday is the culmination of almost three years of intense diplomacy between former Cold War foes. Behind the scenes is another more human and less well known story, of a rising black politician and a Cuban American exile who met for the first time over a cigarette break at a 2003 Chicago fundraiser.

At the time Obama was still an unknown figure in American politics, at least outside his home state of Illinois, and was preparing a bid for the U.S. Senate. The other smoker – both were trying to give up the habit - was Joe Arriola, manager of the City of Miami at the time.

When the two men stepped outside to light their cigarettes, Obama got his first taste of an emerging new current in Cuban American exile thinking.

"He said ‘tell me about the Cubans in Miami,’” Arriola recalled.

“I told him not to listen to the crazy right-wing exiles ... that my kids’ generation thought differently from us older guys and were ready to try a different approach," said Arriola, 69, interviewed over coffee at the Riviera Country Club in Coral Gables where its well-heeled members include some of Miami’s Cuban American elite.

The Man Who Shaped Obama's Cuba Policy Univision

The large Cuban American community makes up 34% of Miami-Dade County’s population, and traditionally was a solid Republican Party voting bloc, largely due to the failure of the John F Kennedy administration to fully support the 1961 Bay of Pigs invasion by Cuban exiles.

“I explained to him there was also a whole new generation of Cubans who have been coming over more recently, who unlike most of my generation have kept their ties to the island. They have relatives there who they send remittances to,” he added.

“The embargo has got to go,” Arriola insisted, referring to the five decades old trade and economic embargo against Cuba.
“It just plays into the hands of the Cuban govenrment,” he said. “It gives them an excuse for everything.”

Go-to guys in Miami

Arriola, and his two sons – businessman Ricky and banker Eddy - quickly become Obama’s go-to guys in Miami.


The Arriolas assembled a core group of likeminded moderates; all middle-aged Cuban Americans frustrated by the longstanding deference of Washington to exile hardliners who held fast to the embargo and rejected dialogue with Cuba’s communist leaders.

It is perhaps bizarre that an informal coterie of influential Cuban Americans in Miami were among the first to see Obama’s political potential. But they seized the opportunity with zeal - secretly at first - to make him a vessel for a radical shift in U.S. policy towards Cuba.

El perfil de la comunidad cubanoestadounidense de Miami está cambiando.
El perfil de la comunidad cubanoestadounidense de Miami está cambiando.

Arriola laughs now when he recalls how he came to be in Chicago that day, invited by an African-American management consultant, James Lowry, who he befriended years earlier while working on minority issues.

Lowry had phoned to invite his friend to a fundraiser for a young politician named Barack Obama, Arriola remembers chuckling. “I told him ‘you want to elect a guy with a name like Barack!’” he blurted out in disbelief.

“Lowry replied, ‘No, no, this guy is really good.’”

Over the cigarettes Arriola realized Obama had little idea about Cuba. “Why should he? At that stage he had little foreign policy experience, but he listened,” he said.

When they parted,” I told him ‘I’d like to do a fund-raiser in Miami for you,” Arriola said.

In June 2004 Obama wowed the audience at the Democratic Party’s national convention, delivering the keynote address, dramatically raising his national profile.

Arriola invited Obama to Miami a few months later for his own fund-raiser, which Obama gladly accepted.

A dozen Cuban American friends and their wives gathered at the home of a wealthy developer, Jorge Perez. They kept it secret as Arriola was a public official and Miami Mayor Manny Diaz was also a guest.

There would have been hell to pay if word had gotten out in Miami’s Cuban media, smiles Arriola, who now serves as chairman of the board of Miami’s largest public hospital network.

El acercamiento a Cuba ha sido una de las grandes apuestas de Obama en p...
El acercamiento a Cuba ha sido una de las grandes apuestas de Obama en política exterior.

Obama walked away with checks totaling around $50,000.

"We brought him down several times after that. He would have breakfast with us and we would pick up people to introduce to him," Arriola said.

When Obama launched his presidential campaign, Ricky and Eddy Arriola joined his campaign finance committee, headed by wealthy Chicago real estate entrepreneur, Penny Pritzker, currently Obama’s Secretary of Commerce.

In 2007 Obama brought his campaign to Miami and surprised exiles by advocating for dialogue with Cuba, as well as lifting restrictions on travel to the island and remittances for Cuban exiles.

"He was more aware of things that I thought he would be,” said Carlos Saladrigas, a Cuban American business executive who was one of the guests at Obama’s first Miami fund-raiser.


Saladrigas, 68, founded the Cuba Study Group in 2001 to seek peaceful change in Cuba through dialogue. He credits the Arriolas with getting Obama’s ear early on. “They saw the potential and brought him to Miami and got him immersed," said Saladrigas.

“Over time they had a lot of inter-action with him in Chicago, and a lot of opportunity to influence Obama’s circle of friends,” he added.

Business engagement

The effort to unfreeze Cuba policy got more heft after the Brookings Institution, a prestigious Washington think-tank, concluded in 2009 that the U.S. “should adopt a policy of critical and constructive engagement, phased-in unilaterally.”

Obama also reached out to younger Cuban Americans. Principal among them was Felice Gorordo, 33, a businessman and former White House fellow, who co-founded the group Roots of Hope which advocates greater engagement between Cuban American university students and youth on the island.

“We believe in greater contact and connectivity to empower young people in Cuba,” he said. “Our fundamental belief is that no one should feel like they need to flee their homeland due to the lack of freedom and opportunities.”

Other influential Cuban Americans later came on board, among them Florida sugar magnate Alfonso “Alfy” Fanjul, Mike Fernandez, a billionaire healthcare executive and major donor to Jeb Bush’s presidential bid, and Carlos Gutierrez, former Commerce Secretary under President George W. Bush.

In late 2012 the highly influential U.S. Chamber of Commerce launched its own initiative to explore private sector support in Cuba, including three meetings with Raul Castro. “The visible shift in the government almost embracing those who promote free enterprise was about as a dramatic a shift as one could imagine in almost six decades,” said Jodi Bond, the chamber's vice president of the Americas.


In Nov 2015 the chamber deepened its commitment, creating a U.S.-Cuba Business Council to advocate on behalf of U.S. companies. Arriola, Fernandez and Gutierrez all sit on the council.

All will be in Havana this weekend when Obama will meet with Cuban president Raul Castro, as well as political dissidents, and deliver a highly anticipated speech directed to the Cuban people.

U.S officials say the new Cuba policy was designed in large part to respond to changing views in the Cuban American community including older exiles like Arriola, a former diehard Republican who left Cuba in 1960, and only recently returned to visit the island.

Arriola’s family lost homes and businesses in Cuba after Fidel Castro took power in 1959. A relative was executed by a firing squad, another later died at the Bay of Pigs. His views began to change after the 1996 shoot down by Cuban fighter jets of two small Miami planes searching for Cuban rafters over the Straits of Florida.

The incident scuppered a diplomatic effort to pressure Cuba to open up its system. “It was evident that the Cuban government didn’t want to open the doors, they were afraid of dialogue,” he said. Others cite Pope John Paul II’s visit to the island in 1998 as a turning point.

Good advice

The advice the White House absorbed from Arriola and others turned out to be spot on. In 2008, Saladrigas recalls being interviewed by president-elect Obama in Chicago for a position in the new administration.

“He was keenly aware of the impact that our polling had had on his campaign strategy,” added Saladrigas. “In essence it enabled him to secure victory in Florida,” he added, noting that Obama won a record share of the Cuban American vote for a Democratic party presidential candidate.

Una casa en La Habana muestra la simbiosis entre símbolos
Una casa en La Habana muestra la simbiosis entre símbolos

In 2012 Obama nearly matched the Republican party among Cuban Americans.

Obama’s December 2014 announcement of plans to normalize relations with Cuba aroused only minor protests. Opinion polls show Cuban American support for a policy of engagement continues to grow.

“You people who have been pressing for this policy, you made a big difference,” White House national security adviser Ben Rhodes, told a town hall of young Cuban Americans at Miami Dade College last week.

“This was not an easy call for the president politically,” he added, saying some in the White House were concerned about backlash from hardline exiles.

“I don’t know that we would have done this if we couldn’t see … that there were going to be people who would support this and try to make it work,” Rhodes said.

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