Fresh off his 2012 re-election victory, President Barack Obama summoned senior advisers to a series of meetings, asking them to "think big" about a second-term agenda, including the possibilities of new starts with long-standing U.S. foes such as Iran and Cuba. Two years later, after painstaking secret diplomacy on separate but surprisingly similar tracks, efforts...

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Fresh off his 2012 re-election victory, President Barack Obama summoned senior advisers to a series of meetings, asking them to “think big” about a second-term agenda, including the possibilities of new starts with long-standing U.S. foes such as Iran and Cuba. Two years later, after painstaking secret diplomacy on separate but surprisingly similar tracks, efforts with Tehran and Havana are in full swing.

The nuclear negotiations with Iran continue and are far from a guaranteed success. But Wednesday’s announcement that the U.S. and Cuba will normalize relations after more than 50 years of hostility suggests one of the last chapters of the Cold War may be closing.

The U.S. outreach to Cuba started cautiously in 2013 in the early months of Obama’s second term, predicated on the idea that no improvement was possible unless the communist government released American contractor Alan Gross, arrested and imprisoned in Cuba on espionage charges.

In their first conversation after Obama named John Kerry his new secretary of state, the two discussed Gross’ ongoing incarceration in Cuba and their broader dissatisfaction with America’s policy toward the island. Kerry quickly enlisted the assistance of the Vatican, one of the few institutions in the world broadly respected in the U.S. and Cuba. The Roman Catholic Church’s help would prove significant.

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Behind the scenes, Obama began putting the wheels of his secret diplomacy in motion, according to senior administration officials. They weren’t authorized to publicly provide a diplomatic timeline and demanded anonymity.

In spring 2013, the president authorized two senior aides to sit down with representatives of the Cuban government for exploratory talks. It was an effort that roughly coincided with similarly covert discussions Obama was directing in the Middle East between U.S. and Iranian officials over that country’s contested nuclear program.

Whereas Muscat, Oman, and Geneva, Switzerland, served as the venues for Iran negotiations, the Canadian cities of Ottawa and Toronto and Vatican City hosted Cuba talks.

In June of last year, Ben Rhodes, Obama’s deputy national security adviser, and Ricardo Zuniga, an adviser on Latin America, traveled to Canada for the first of nine meetings with their Cuban counterparts. Most took place in Canada.

The U.S. officials would not name the Cubans they met with but described them as government officials empowered by Cuban President Raul Castro to talk with the U.S. Canada’s government was not directly involved in the negotiations, playing a role of facilitator similar to that of Oman halfway across the world in secret negotiations between the U.S. and Iran.

But earlier this year another powerful mediator would forcefully enter the process with Cuba: Pope Francis.

The first Latin American pontiff raised the possibility of a Cuba rapprochement with Obama in March, when the U.S. president visited the Vatican. Then, in the summer, he sent Obama and Castro letters urging them to end the decades-long freeze.

Kerry, meanwhile, held four telephone calls over the same period with Cuban Foreign Minister Bruno Rodriguez. The calls focused on Gross, senior administration officials said, with Kerry telling the Cubans that if anything happened to the 65-year-old Maryland native their chances of better relations with the U.S. would be over.

At the Vatican this fall, U.S. and Cuban officials worked to finalize the deal that would free Gross and pave the way for a new U.S.-Cuban relationship.

Discussions continued, culminating in Tuesday’s 45-minute phone conversation between Obama and Cuban President Raul Castro — the first presidential-level dialogue between the U.S. and Cuba since Castro’s older brother Fidel seized power in 1959 and the U.S. embargo of the country began in 1961.

Again, the process was strikingly similar to last year’s easing of U.S.-Iran tensions. In that case, Obama and Iranian President Hasan Rouhani held their own telephone call, leading to a historic nuclear agreement and the most engaged discussions between the countries since Iran’s 1979 Islamic Revolution.

As Obama spoke on the telephone with Cuba’s leader, Rhodes, Zuniga and a handful of other top advisers of the president gathered in the Oval Office.

Gross’ release — combined with a U.S.-Cuba spy swap, an easing of American trade sanctions and pledges by each side to restore full diplomatic ties — has broken more than 50 years of American presidents either isolating or actively seeking the overthrow of Fidel Castro or his brother Raul’s government.

When Obama on Wednesday explained to the nation the new path he wanted to take with Cuba, Gross watched from Andrews Air Force Base in Maryland, having just returned from Cuba. At his side was Kerry, whose return flight from a diplomatic trip that included a stop at the Vatican landed on the same runway minutes after Gross’ plane.

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AP White House Correspondent Julie Pace contributed to this report.