It all started when Arizona Sen. Jeff Flake found himself in a dark park in Havana trying to score some ice cream.

Flake, a devout Mormon, doesn’t drink or smoke, so instead of puffing a cigar or sipping some rum, he paid a man a peso in Coppelia Park to indulge in a bit of gelato on one of the first of nine trips he’s taken to the communist country since he first became fascinated with the place 25 years ago.


Those trips, which started in the early 2000s after the Arizona Republican took office, helped solidify his reputation as a leading Cuba-phile in Congress, where he has been one of the most vocal supporters of lifting a decades-old U.S. embargo and opening up travel to the country — bucking his own party in the process.

So this week, when Barack Obama wanted to send lawmakers to pick up American Alan Gross in Cuba, Flake was a natural choice for National Security Adviser Susan Rice to ask to join the two Democrats on the plane — adding a bipartisan flavor to the event that gave the president some cover.

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“I don’t often agree with President Obama, but he was right to begin the process of normalizing relations with Cuba,” Flake said.

Flake’s interest in Cuba predates his time in Congress, to the late 1980s when he joined Foundation for Democracy, a group that helped monitor Namibia’s independence process. He had worked as a Mormon missionary in South Africa before that, learning to speak Afrikaans.

As executive director of the group, Flake helped Namibia’s newly formed government craft its constitution. That sparked his interest in growing democracies abroad.

“The funny thing about freedom is that when people experience a little more of it, they don’t want to give it up, and they want more than they have,” Flake said, arguing that relaxing restrictions in Cuba will help democracy grow. “That has been the case with travel and will continue to be the case in Cuba.”

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It was in Namibia that Flake got his first taste of the Castro regime. The Cuban government sent thousands of troops to support the movement in Namibia, linking the two governments.

“Namibia became independent only after an agreement was reached that, among other things, removed Cuban troops from Angola,” Flake said, explaining how Cuba became a place of interest for him. “So the Cuban issue has kind of been around, in my sphere, for a while at different levels.”

Since then, Flake has come to an intellectual opposition to the embargo. He believes, as many who oppose the embargo argue, that it is not achieving its goals of weakening the communist regime. As a pro-democracy reformer, he believes a different approach would ultimately be more effective.

“For those who say this is a concession somehow to the Cuban regime … I think that that is a wrong way to look at it. That is simply wrong,” said Flake on Wednesday after returning from Cuba. “The policy that we’ve had in place for the past 50 years has done more in my view … to keep the Castro regimes in power than anything we could’ve done.”

He also came to believe that barring Americans from traveling to Cuba is unjust.

“To me it’s just an issue of freedom. We ought to be able to, as Americans, travel wherever we want unless there is a compelling national security reason not to. And for a long time there hasn’t been a reason to prevent us from traveling [to Cuba],” he said.

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Flake’s involvement with the mission this week began with a call from Rice, who asked him on Monday night if he’d join Rep. Chris Van Hollen (D-Md.) and Sen. Pat Leahy (D-Vt.) on the plane the next day. The three lawmakers left around 5 a.m. — a departure Flake hid at first from even senior staff members to keep a lid on Gross’ release. Flake was also briefed about the impending policy changes while on the flight.

Earlier this month, Flake pushed the Obama administration to get aggressive about changing U.S.-Cuban relations. In a December meeting with Rice, Flake outlined what he described as “moderate” proposals the U.S. could adopt without angering Republicans, including allowing American businesses the ability to trade with entrepreneurs and private business.

Flake wrote to Obama on Dec. 11 that he should lift restrictions on remittances and support policies to build Cuba’s domestic Internet infrastructure. The dramatic policy changes Obama announced on Wednesday went beyond what Flake said he thought the administration was prepared to do.

“I was very happy to see he went beyond every one of them with his policy changes,” Flake said. “I would have liked more. I’m pleased with everything the president did, and I hope Congress goes further and removes the embargo. I just didn’t think he was prepared to go as far as he did. I was pleasantly surprised.”

And it’s clear that however the Obama administration ultimately engages Congress over the 50-year-old embargo or an ambassador, Flake will be a key player for the White House when it comes to Republican support. Obama and Flake spoke Thursday evening about Congress’ options. Flake is a respected voice within the Republican conference and has a relationship with senior members of the Cuban government.

Flake is one of only a few prominent Republicans who are supporting Obama on the Cuba changes. Sen. Rand Paul, a likely 2016 presidential contender, and a handful of House Republicans have joined him in support, but Flake was the first, and the most vocal, proponent of Obama’s plan.

And while some Republicans on Capitol Hill are already planning how they might stymie Obama’s plans, Flake offered Obama a bit of bipartisan cover on Wednesday when the news was announced.

The White House has long relied on Flake to offer the administration cover among Republicans when it comes to Cuba policy. When Obama announced in 2011 a policy change to allow Cuban-Americans to more freely travel to the country and send back money to relatives, the White House asked Flake to express disappointment that the reforms didn’t go far enough, a source close to that conversation said.

Flake’s support of a wholesale change in the U.S.’ policy toward Cuba is in line with what he’s said and done for years. He signed on to legislation that would stop the president from banning travel to Cuba for any Americans and co-sponsored legislation with former Rep. Ron Paul (R-Texas) to end the Cuban embargo.

The Arizona Republican’s full-throated endorsement of Obama’s plans has put him at odds with many senior members of his own party — and it is not the first time Flake has found himself as a lonely voice railing against the GOP establishment. During his tenure in the House, Flake was a vocal critic of earmarks even when the funding measures were in vogue. But the GOP eventually changed its tune on earmarks, which were ultimately banned in the House.

His Cuba position is putting him squarely against the Republican establishment and some of the libertarian-leaning GOP lawmakers Flake has found allies in on trade, privacy and marijuana legalization policies. Texas Sen. Ted Cruz, a likely presidential candidate in 2016, called the Obama administration’s announcementa “badly needed economic lifeline” for the Castro regime.

“If history be our guide, the Castros will exploit that power to undermine America and oppress the Cuban people. First Russia, then Iran, now Cuba — this is one more very, very bad deal brokered by the Obama administration,” Cruz said.

And a cadre of Senate Republicans, including Lindsey Graham (R-S.C.) and John McCain (R-Ariz.), quickly criticized Obama’s announcement to normalize relations with the Castro government, saying it was a “retreat and decline” for American foreign policy. Even Republicans who once supported altering how the U.S. interacted with the communist island denounced the White House’s announcement that it would look to open an embassy in Havana to reestablish ties with Cuba.

“I oppose this move, and I believe it is a mistake. It’s hard — if not impossible — to normalize relations with a Castro-led Cuba,” Sen. Roy Blunt (R-Mo.) said.

Blunt was part of a group of GOP congressional leaders in 2000 that crafted an agreement to allow American financial institutions to help bring third-party financing to the island and allow food and medicine to be more easily sent to citizens there.

Across the Capitol, House Republicans also warned of national security threats by recognizing Cuba’s government.

“I’m concerned about long-term ramifications to Americans and soldiers across the globe from yet another prisoner swap. This move sends a message to every rogue government and terrorist organization that this administration is willing to negotiate with them, even if it undercuts U.S. interests and values,” said libertarian-leaning Rep. Matt Salmon (R-Ariz.).

But Flake isn’t without fellow GOP supporters. Incoming House Oversight and Government Reform Committee Chairman Jason Chaffetz (R-Utah) said he finds the current ban on Americans traveling to Cuba “ridiculous.”

“There are other provisions that I really need to study and look at, but the idea of allowing Americans their free choice to make their own decision about going to Cuba — I applaud that and support it,” Chaffetz told KSL radio.

South Carolina Republican Rep. Mark Sanford said Wednesday he would introduce a similar bill to Flake’s travel bill.

“It preserves the right of Americans to travel to Cuba, regardless of who occupies the White House,” Sanford said in a statement. “This is important because actions similar to today’s [to relax travel restrictions] were taken in the 1970s by President Carter and quickly removed when President Reagan took office.”

And Flake said he believes more Republicans will slowly express support a slow normalization of relations with Cuba. Changing the long-held conservative stance on the Cuba embargo — for decades, Cuban-Americans have been loyal Republicans because of the party’s stance on the Castro regime — will take time, but Flake predicted no serious opposition to any ambassador candidate put forward by the Obama administration if it is a career foreign service official.

“There are others, who haven’t been as vocal perhaps, that have always pushed for changes on travel. I think other Republicans will be coming forward soon,” Flake said. “If he appoints somebody with good credentials, I don’t think, despite what we’ve heard from some of my colleagues, we’ll have a big fight on it.”

Seung Min Kim contributed to this report.