Why the Cuba deal happened now

Cuba’s release Wednesday of U.S. government subcontractor Alan Gross after nearly five years’ imprisonment virtually eliminates the last major impediment to better relations with Havana.

“These are definitely the first steps at tearing down the embargo,” said Ted Henken, a Cuba expert and chair of the Sociology and Anthropology Department at New York’s Baruch College. “That’s the spirit of what’s happening today. That is huge.”

President Barack Obama said he spoke with Cuban President Raul Castro Tuesday in a phone call that lasted about an hour and reflected the first communication at the presidential level with Cuba since the Cuban revolution.

The president announced plans to normalize diplomatic relations with Cuba and ease economic restrictions on the nation, a policy shift he called the end of an “outdated approach” to U.S.-Cuban relations that “for decades, has failed to advance our interests.”

Gross, held by the Cuban government since 2009 for smuggling satellite equipment onto the island, was freed as part of a landmark deal that paves the way for a major overhaul in U.S. policy toward the island.

The move comes midway through Obama’s second term and represents a significant thaw in relations between the United States and Cuba. Senior administration officials and Cuba observers have said that reforms on the island and changing attitudes in the United States created an opening for better relations.

Gross’ “humanitarian” release by Cuba was accompanied by a separate spy swap, the officials said: Cuba freed a U.S. intelligence source who has been jailed in Cuba for more than 20 years, although authorities did not identify that person for security reasons, and the U.S. released three of five Cuban intelligence agents convicted of espionage in 2001.

Senior administration officials recently acknowledged that talks about a swap between Gross and the three Cuban agents – part of group originally known as the Cuban Five – had been taking place. In addition, recent editorials in The New York Times recommended an end to the longstanding U.S. embargo against Cuba and a prisoner swap for Gross, signaling a changing national attitude on Cuba policy.

Proposed policy change splits Cuban-Americans along generational lines

The timing is right

With the U.S. midterm elections over, some Cuba observers say the time was ripe for a breakthrough in relations. As a second-term president, Obama doesn’t have to worry about re-election.

“He doesn’t have anything to lose,” Henken said of the president.

William LeoGrande, an American University professor and co-author of a new book, “Back Channel to Cuba,” which chronicles decades of negotiations between the two countries, was in Cuba Wednesday for the landmark announcement.

“This is an historic development in U.S.-Cuban relations, and hopefully a step toward full normalization of relations,” he said via email. “Obama’s actions represent the most positive actions to improve relations since President Carter.”

A declassified presidential directive, signed by Carter in March 1977, stated: “I have concluded that we should attempt to achieve normalization of our relations with Cuba.” The directive is believed to represent the only time a president ordered normalization of U.S. relations with Castro’s Cuba to be an explicit foreign policy goal of the United States. In 2002, Carter became the first U.S. president, current or former, to visit Cuba since Castro’s 1959 revolution.

LeoGrande said recently that “the political stars are well aligned because both Obama and Raul Castro have repeatedly said that they’d like to see an improvement in relations. ”

In April 2015, at the Summit of the Americas in Panama, the two leaders will have an opportunity to meet face-to-face.

The White House can lay the groundwork for agreements aimed at “burying the historical hatchet between the U.S. and Cuba,” said Peter Kornbluh, co-author of “Back Channel to Cuba” and senior analyst at the National Security Archive.

“Richard Nixon went all the way to China, and Barack Obama only has to go to Panama,” he said.

In Washington, senior administration officials predicted more cooperation, with an important caveat.

“There is stuff we can do, but it has to start with Gross,” one of the officials said recently, before Gross’ release.

Wayne Smith, a former head of the U.S. Interests Section in Havana, praised the timing of the announcement, saying it’s good news following the release of a damaging report chronicling U.S. torture of terror suspects after 9/11.

“The United States is the only country now that does not have full diplomatic relations with Cuba,” Smith told CNN in Havana. “One of the marks in the hemisphere against the United States is its outdated Cuba policy. So we are now moving … to change our Cuba policy to begin to engage with Cuba. That’s exactly the right thing to do.”

Time for a change

Without congressional approval, the Obama administration is taking significant steps to improve relations with Cuba.

“It seems that there are going to be direct talks between the governments that will go far beyond migration, which has been basically the limit of the talks until now,” Henken said. “The administration is announcing that they’re going toward full diplomatic relations. That’s the end goal. We’ve never heard that in 50 years.”

For instance, the president can eliminate the travel ban and allow all Americans, not only Cuban-Americans, to go to the island nation by granting “general licenses” for travel to Cuba.

On Wednesday, Obama said the United States will move toward reopening its embassy in the communist nation and allow some travel and trade that had been banned under a decades-long embargo imposed during the Kennedy administration

While the more liberal travel restrictions won’t allow for tourism, they will permit greater American travel to the island.

In a boost to the nascent Cuban private sector, the Obama administration will allow expanded commercial sales and exports of goods and services to Cuba, particularly building materials for entrepreneurs and private residences, and allow greater business training, as well as permit greater communications hardware and services to go to the island.

“I believe this contact will do more to empower the Cuban people,” Obama said Wednesday in announcing the new approach in Cuba policy.

Other announced changes permit U.S. and Cuban banks to build relationships and travelers to use credit and debit cards. U.S. travelers will be allowed to import up to $400 worth of goods from Cuba, including $100 in alcohol and tobacco – even Cuban cigars. Remittances by Americans to their families back in Cuba will also be increased to approximately $2,000 per quarter.

The United States will also review Cuba’s designation as a state sponsor of terrorism, Obama said.

“Cuba doesn’t belong on the list anymore, if it ever did,” LeoGrande said. “If you read the last report on state sponsors of international terrorism put out by the State Department, you see that for every point made in explaining why Cuba is on the list, there follows an explanation of how much better Cuba is behaving on that point.”

Little fallout

The White House came under fire after the recent swap of five Taliban detainees for the release of U.S. Army Sgt. Bowe Bergdahl.

Bergdahl was freed last spring after nearly five years in captivity at the hands of militants in Afghanistan. His controversial release came in exchange for five mid- to high-level Taliban detainees from Guantanamo Bay Naval Base in Cuba.

“They’ve been in jail for 16 years,” LeoGrande said of the Cuban agents, “and on humanitarian grounds alone it’s reasonable to release them when we stand to gain the release of an American citizen.

“It’s a better deal than trading five Taliban commanders for one U.S. soldier.”

No one knows how the incoming Republican-controlled Senate will handle Cuba policy. Most Republicans don’t feel strongly about the Cuba issue, and some lawmakers in agricultural states have supported a lifting of the trade and financial embargo in force for more than 50 years.

With Sen. Robert Menendez, D-New Jersey, soon to be replaced as chairman of the Senate Foreign Relations Committee, one of the most powerful opponents to greater engagement with Cuba will have a decreased platform from which to criticize the administration on Cuba issues. But Menendez will remain on the committee, as will Sen. Marco Rubio, R-Florida, another strong Cuba critic.

While the release of Gross drew widespread praise, Republican lawmakers criticized the overall move on Cuba policy.

Rubio told CNN he would do everything in his power to block any potential U.S. ambassador to Cuba from even receiving a vote.

Rubio promised that as incoming chairman of the Senate Foreign Relations Committee’s Western Hemisphere subcommittee, he’ll “make every effort to block this dangerous and desperate attempt by the President to burnish his legacy.”

Isolation hasn’t worked

A senior Senate aide familiar with the Cuba issue said the drumbeat for improved relations with the island always comes in the waning years of every Democratic administration. The aide said it was “politically hard to believe” that the Cuba issue will take precedence over critical foreign policy challenges Obama faces around the world.

Despite the move toward normalized relations, Obama said he still wants to support increased freedoms for citizens there. “I do not expect the changes I’m announcing today to bring about a change in Cuban society overnight,” he said.

But the president argued that “isolation has not worked” in 50 years and that more could be accomplished through engagement.

“Neither the American nor Cuban people are well-served by a rigid policy that’s rooted in events that took place before most of us were born,” Obama said.

Still, Washington has taken a big first step.

“We are charting a new course toward Cuba,” a senior administration official said. “The President understood the time was right to attempt a new approach, both because of the beginnings of changes in Cuba and because of the impediment this was causing for our regional policy.”

But some longtime Cuba observers are skeptical broader changes will follow.

“(Attorney General) Eric Holder is leaving … and Obama is now pretty much a lame duck, and Bob Menendez will no longer be chairman of foreign relations, and Alan Gross should be home by Thanksgiving or Christmas or Hanukkah,” said Fulton Armstrong, a former a senior adviser to the Senate Foreign Relations Committee under then-Sen. John Kerry when Gross was arrested. “Enough is enough. But we’ve been at this point before.”

It’s happened before

In “Back Channel to Cuba,” LeoGrande and Kornbluh describe backdoor negotiations in 1963 that led to the release of more than two dozen Americans jailed in Cuba, including members of a CIA team caught planting listening devices in Havana.

The United States gave up four Cuban prisoners, including an attaché at the U.N. mission and two indicted for planning acts of sabotage. The fourth was a Cuban convicted of murder for killing a 9-year-old girl who was struck by a stray bullet during a fight with anti-Castro Cubans when Fidel Castro visited New York in 1960.

Castro granted clemency to the American prisoners. And the United States released the Cubans in what the Justice Department described as an act of clemency “in the national interest.”

In 1979, President Jimmy Carter granted clemency and released three Puerto Rican nationalists, including Lolita Lebron, who had been convicted for opening fire in the U.S. House of Representatives and wounding five congressmen. The deal was part of a backdoor “humanitarian exchange” in which Fidel Castro released four CIA agents 11 days later.

Said Kornbluh, “It is time to bring U.S.-Cuba relations into the 21st century.”

CNN’s Elise Labott contributed to this report.