President Raúl Castro of Cuba and President Barack Obama shake hands during a bilateral meeting at the United Nations in New York City on Sept. 29, 2015.
Anthony Behar-Pool/Getty Images

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 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, Fla., where its well-heeled members include some of Miami’s Cuban-American elite.

The large Cuban-American community makes up 34 percent of Miami-Dade County’s population and was traditionally a solid Republican Party voting bloc, largely because of 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,” Arriola said.

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

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

The Arriolas assembled a core group of like-minded moderates, all middle-aged Cuban Americans frustrated by the long-standing deference of Washington, D.C., 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 toward Cuba.

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David Adams is a digital journalist at Univision News. Follow him on Twitter.