Facing President Donald Trump in the Oval Office, Florida Sen. Marco Rubio issued a blunt warning: The administration’s plan to crack down on Cuba trade and travel was under threat.

Any effort by Trump to make good on his campaign promise to roll back former President Barack Obama’s historic accord with Raul Castro would be delayed, Rubio cautioned—not just from the Castro government and from outside business interests, but from within. It would be studied to death by government analysts who favor more engagement with Cuba, not less. It would be leaked to the news media. Stillborn with a thousand excuses by the bureaucrats.


So go it alone, Rubio told the president during their May 3 meeting.

“What you’ve committed to do on Cuba, what you want to do on Cuba, is never going to come from career staff. It’s going to have to come from the top down. You’re going to have to tell them what to do,” Rubio recalled telling the president as his fellow Miami Republican member of Congress, Rep. Mario Diaz-Balart, nodded in agreement.

“The career service people, in the State Department and Treasury and in other places, are not in favor of changing this policy,” Rubio recalled telling the president.

That one piece of advice from Rubio probably marks the moment that Trump’s Cuba policy achieved escape velocity, according to interviews with eight officials who helped craft or had knowledge of the drafting of Trump’s Cuba policy as well as correspondence and documents shared with POLITICO.

On Friday, the president will appear in Miami, the home base of the Cuban-American exile community to announce the new crackdown on Cuba.

The policy bears the unmistakable fingerprints of Rubio — a Trump antagonist during the Republican primary campaign last year who has grown increasingly close to Trump — and Diaz-Balart, also a staunch critic of Obama’s moves to normalize ties with the island nation.

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Their meeting with Trump, at 6 p.m. on a busy Wednesday in between the president’s meeting with Palestinian President Mahmoud Abbas and a dinner with evangelical leaders, included top administration officials, underscoring the importance of the issue for Trump. The president sat facing Rubio and Diaz-Balart on the right and left, respectively, of the Resolute Desk.

To Rubio’s right sat Homeland Security Secretary John Kelly. To Diaz-Balart’s right was Secretary of State Rex Tillerson and, to his right, was national security adviser H. R. McMaster. On the couch behind Rubio sat White House chief of staff Reince Priebus and on the other couch, behind Diaz-Balart, was the president’s son-in-law and adviser, Jared Kushner.

After Rubio and Diaz-Balart pitched their warnings about bureaucratic opposition to cracking down on Cuba, Trump had a simple question: “OK. How do we deal with this?”

McMaster piped up: “I will lead this. I’ll get this done.”

“That’s when things started moving, started moving real fast,” Diaz-Balart told POLITICO, recalling the snippets of conversation.

Secrecy was essential. Trump’s circle of trust was small.

They wanted to prevent media leaks, fearing that other politicians and Cuba-aligned businesses would exploit any opening. But they were more concerned that electronic copies of policy memos could fall into the hands of foreign agents, including Russia, which has a long-standing friendship with the Castro government. So draft proposals were circulated by paper and hand-delivered between the White House, Rubio and Diaz-Balart’s offices and the National Security Council, which oversaw the development of the six-point, eight-page Presidential Policy Directive from Trump.

In one case, Florida Gov. Rick Scott personally handed a Diaz-Balart memo to Trump as the two rode in the presidential limousine with Rubio to an event in Orlando.

At the heart of Trump’s plan, obtained Thursday by POLITICO, is a clear prohibition on tourist travel and a restatement of the goals of the 56-year-old U.S.-Cuba embargo after it was codified into federal law in the 1996 LIBERTAD Act that Diaz-Balart’s brother, Lincoln Diaz-Balart, helped push through Congress when he was a House member.

The directive also prohibits U.S. travelers and businesses from generally engaging in most financial transactions with entities owned or substantially controlled by the Cuban military holding company called “Grupo de Administracion Empresarial S.A.,” known as GAESA. Since GAESA has de facto control over nearly every major part of Cuba’s economy — especially restaurants and hotels in Old Havana and along the famed beaches of Varadero — the prohibition would effectively intensify the embargo.

The GAESA prohibition last surfaced June 3, 2015, when Rubio announced it as a bill called the “Cuban Military Transparency Act.” Weeks later, the House Intelligence Committee introduced a companion at the urging of Diaz-Balart and Miami’s other Cuban-American Republican House members, Carlos Curbelo and Ileana Ros-Lehtinen. Though it’s unclear who gets the credit for the original GAESA bill, it became more of Rubio’s central focus in helping Trump formulate his policy.

Opposition to Castro runs in the family for Diaz-Balart. His aunt was Fidel Castro’s first wife, and his cousin bears the diminutive nickname of the deceased dictator—“Fidelito.” Diaz-Balart admittedly had a broader “kitchen sink approach” where he’s asked for everything he could — and made sure to repeatedly stress the broader issue of human rights and a return to the principals of the LIBERTAD Act.

Unlike Rubio or Diaz-Balart, Trump has had an inconsistent record on Cuba.

In 1999, when he was considering an independent bid for president, Trump gave a stemwinder speech in which he condemned the brutality of the Castro regime and pledged not to do business there. But the year before, according to a Newsweek report, Trump sent an emissary to examine casino opportunities on the island. And in 2015, Bloomberg Businessweek reported last year, Trump Organization officials scouted for a possible golf course deal in Cuba.

At the outset of his presidential campaign in 2015, Trump said Obama’s rapprochement with Cuba was “fine,” though he thought the United States “should have made a stronger deal.” During a primary debate, Trump clashed with Rubio by saying he was “somewhere in the middle” on Cuba policy, while Rubio called for a reinforcement of the embargo.

“Here's a good deal — Cuba has free elections, Cuba stops putting people in jail for speaking out, Cuba has freedom of the press,” Rubio said, an echo of Trump’s Miami speech in 1999. “Cuba takes all of those fugitives of American justice, including that cop killer from New Jersey, and send her back to the United States and to jail where she belongs. And you know what? Then we can have a relationship with Cuba. That’s a good deal.”

By September 2016, Trump had morphed back into a hard-liner.

“All the concessions that Barack Obama has granted the Castro regime were done through executive order, which means the next president can reverse them — and that I will do unless the Castro regime meets our demands. Not my demands. Our demands,” Trump said, as 2,500 supporters cheered him on.

On Dec. 18, 2014, Sen. Marco Rubio stands near a poster with pictures of those lost from the group called "Brothers to the Rescue" when they were shot down by Cuban fighter jets in 1996, as he and other members of Congress address the decision by President Barack Obama to change the United States' Cuba policy. | Getty

“Those demands are religious and political freedom for the Cuban people. And the freeing of political prisoners,” Trump said before questioning whether he hit the correct pro-embargo notes: “Is that right?”

The crowd cheered.

Part of Trump’s commitment to rolling back Obama’s policy stems from his desire to put a political win on the board without having to rely on Congress, where a growing number of members support lifting the embargo and allowing Cuba travel. Polls of the U.S. public at large and even of Cuban-Americans show that majorities support Obama’s normalization policies.

But the White House says that, while trade has increased with Cuba, repression has risen as well. The new Trump policy, said a senior White House official, is based on “President Trump’s core conviction that what the Cuban exile community is asking for is right and just.”

“The oppressors of the Cuban people are the Cuban government, who have increased repression on the island against dissidents and Ladies in White since reestablishing diplomatic relations,” the White House official added. “Prior to that, it was not clear to some if the Obama policy toward Cuba would work; today it is clear that the Obama policy toward Cuba does not.”

The White House official said Trump’s commitment is deeply personal as well, the result of a visit in the final week of the election to the Bay of Pigs Museum in Little Havana, where he received the endorsement of the Brigade 2506, veterans who survived the disastrous invasion effort to topple Castro. It was the group’s first endorsement in five decades.

Still, Trump was clobbered by Hillary Clinton in Miami-Dade County, but he ultimately won Florida by a narrow margin and he credited the Bay of Pigs veterans for standing by him when it looked as if he would be a sure loser.

“He always brings them up,” Diaz-Balart said. “I don’t know if it’s the fact they were betrayed by our government. I don’t know what it is. It’s something that obviously affected him. But he told them and he told me and he told Marco, ‘I’m with you on Cuba.’ And I knew then he’s not going to lie. He’s not going to betray the community at large. And he’s not going to betray the Bay of Pigs heroes.”

Trump was so committed to the brigade that he wanted to announce his new policy Friday at the Bay of Pigs museum, but the venue was too small. So he chose a Miami theater that bears the name of Manuel Artime, a Bay of Pigs leader.

The group came up in Trump’s first call with his onetime rival Rubio after the election in November. Rubio, who made a successful late bid to retain his Senate seat after dropping out of the presidential race, was at the local Dadeland Mall with his family when he called the president-elect. Rubio, who got crushed in Florida by Trump in the GOP presidential primary, ran for reelection and ultimately won far more votes than Trump, a point the senator jokingly brought up.

“We have to do something on Cuba,” Trump told Rubio, once again mentioning the Bay of Pigs veterans.

A little more than two weeks later, Fidel Castro died, prompting a celebratory Trump tweet as the news broke the morning of Nov. 26: “Fidel Castro is dead!”

Scott also talked to Trump about Cuba during the transition. Scott, a multimillionaire and political outsider like Trump, said his main advice to the president-elect was to make one person in charge of his Cuba policy; don’t leave it up to multiple underlings, a message the governor repeated during numerous calls and meetings, including a Feb. 6 event at MacDill Air Force Base in Tampa.

About a week later on Feb. 15, Rubio, Trump and their wives dined together at the White House. Trump, again, brought up Cuba. The two also discussed the destabilizing situation in Venezuela, which has an affinity with the Castro government. But Cuba was more on his mind.

“I want your ideas on Cuba,” Trump said.

The Florida Republicans began circulating Cuba policy proposals with the Trump administration. Diaz-Balart typed up a seven-point memo titled “A Good Deal that Upholds the Law and Protects National Security” that called for more democracy, an independent judiciary and the return of fugitives from justice, including wanted New Jersey cop-killer Joanne Chesimard.

One media report claimed that Diaz-Balart offered Trump to trade his vote in support of the unpopular American Health Care Act that replaces Obamacare in return for Trump’s support of Cuba policy — but Diaz-Balart called the story a “lie.” But he acknowledges talking about Cuba to “anyone who would listen” and handed a copy of his memo to Scott, who was in Washington with other Republican governors and was to meet with Trump three days later in Orlando at a school-choice event.

Rubio joined Trump on Air Force One for the flight down. He sat in the rear of the plane, which Trump didn’t realize until he walked back.

“What the hell are you doing here?” Trump asked the senator, Rubio recalls. “Come up front.”

Scott met them at the airport and, after they piled into the presidential limo, the governor handed over Diaz-Balart’s memo. Scott had his own ideas, mainly about tone and focusing on Castro’s human rights record. Rubio gave his input and mentioned GAESA and four other points concerning travel and trade limitations.

“Can you guys put something together and bring it to us?” Trump asked.

Rubio and Scott first thought of writing a memo but then decided it would be best to write an open letter to him that would be co-signed by Diaz-Balart, Curbelo and Ros-Lehtinen. Sometime in mid-March, they sent it off. They heard nothing for more than a month.

Diaz-Balart said he “never had any doubts in my conversations with the president” about his objectives, but he worried government inertia was taking its toll. The exile community back home was getting restless.

“There was a time I was concerned that the business community may have gotten to him telling him, ‘you can’t change it. It’s too late. It’s irreversible,’” Diaz-Balart said. “A lot of the work had progressed and then all of a sudden, it kind of died. And it kind of died because, in essence, the White House folks were pushing for it but the bureaucrats were saying ‘no’ and raising a million reasons it couldn’t happen and couldn’t happen and couldn’t happen.”

Then, on April 27, the so-called open letter came back from federal officials with edits that confirmed the worst fears of the Cuba hard-liners from Florida.

Where the Republican politicians wanted to call on Trump to issue an action that “freezes” general licenses for transactions with Cuba, the language was watered down to a “review,” according to a copy of the letter obtained by POLITICO. The call to "adopt" the thrust of the GAESA bill to punish the Cuban military was instead changed to a suggestion that Trump merely "consider" it. And an unnamed official struck out on a call to make sure tourism remained banned “through the elimination of licenses for non-academic educational travel.”

At 8:17 p.m. Rubio was waiting to catch the last flight home from Washington and called Priebus. “Guys, it’s time to get going on this,” Rubio recalled saying. “This study idea is not going to fly. This is not what we’re going to do. And it’s not what the president is going to do.”

Six days later, at that May 3 meeting, Rubio and Diaz-Balart sat in the Oval Office and together pitched the president.

As the policy took shape, the Cuban government grew increasingly nervous as did businesses, travel groups and Democrats who had lauded Obama’s normalization moves in 2014.

The Cuban government sent signals through the news media and diplomatic channels that it was ready to negotiate and, according to a Rubio aide, it pressured Colombia to weigh in by suggesting it might withdraw from an unrelated U.S.-led Latin American conference that began Thursday in Miami and runs until Friday, when Trump makes his announcement nearby.

In an earlier interview, Rubio said he expected the Cubans would bring multiple pressure points to bear, including attempts at trying to drive a wedge between him and Trump.

“Getting rid of the embargo is their top foreign policy objective,” Rubio said. “And the president’s policy sets them back.”