A family in Havana watches the return of Cuban spies released by the U.S.
Redux for TIME
December 22, 2014 9:25 AM EST

Near the beginning of a speech on Dec. 17 announcing that the U.S. and Cuba would begin to resume full diplomatic relations after more than 50 years, President Barack Obama made a personal aside. “I was born in 1961,” he said, “just over two years after Fidel Castro took power in Cuba and just a few months after the Bay of Pigs invasion.” The point was clear: Americans and Cubans had been living in thrall to a history that had unfolded before most of them had even been born. People had changed, but the policy hadn’t. It was long since time to break free.

But if Obama and his Cuban counterpart, Raúl Castro, put an overdue end to one era of Cuban-American relations, it remains unclear what the future will look like. The trade embargo is still in place, if weakened by Obama’s actions, and while American businesses are eager to seize a piece of paradise, the Cuban government still controls the economic levers. The Castro regime remains firmly in power, a fact not lost on the many Cuban Americans who saw Obama’s move as a betrayal. “It may well strengthen the Castros and entrench a new generation of their oppressors in power unless Congress steps in to stop it,” Cuban-American Senator Ted Cruz wrote on TIME.com.

Just negotiating the deal was difficult enough, requiring a year of secret talks between the two countries, with an assist by Pope Francis. It wasn’t until Cuba agreed to release Alan Gross, a 65-year-old American contractor who had been convicted of espionage by a Cuban court in 2011, that the historic shift became a possibility. (The U.S. and Cuba also made a separate swap of spies.)

The prisoner releases paved the way for Obama to loosen restrictions on trade, travel and diplomacy. Secretary of State John Kerry will launch efforts to re-establish an embassy in Havana. He will also review Cuba’s place on the list of state sponsors of terrorism, where it has been since 1982, even as countries like North Korea have been taken off. And Americans will be allowed to send more money to the island nation–Cuban emigrés in the U.S. already give some $2 billion a year to families back home–and more easily visit the nation just 90 miles (145 km) away. “This is the culmination of years of analytic and intellectual legwork,” says Julia Sweig, director of Latin American Studies at the Council on Foreign Relations.

Of course, not everyone was so impressed. Republican Senator Marco Rubio of Florida, a possible 2016 presidential candidate, ripped the deal. “The entire policy shift announced today is based on an illusion,” he said. “The White House has conceded everything and gained little.” Carlos Gutierrez, a Cuban-American businessman and Commerce Secretary under President George W. Bush, told TIME that Obama got the worst of the deal. “This is a major political win for Raúl Castro.”

U.S.-Cuban relations have been frozen largely because of such sentiments among Cuban Americans, who for decades opposed any rapprochement with the Castro regime. The danger of offending a powerful voting bloc in the key swing state of Florida was more than enough to keep national politicians from both parties in line–and the Cuba embargo firmly in place.

But the demographic tilt of the Sunshine State is changing. The growing numbers of Hispanic immigrants from Puerto Rico and other parts of Latin America don’t share the Cuban emigrés’ deep-seated, personal hatred of Fidel. And while many older Cuban Americans still support the embargo, their children and grandchildren are in favor of more relaxed travel and trade with Cuba. A 2014 Florida International University poll of Cuban Americans in the Miami area found that 68% were open to the possibility of restoring diplomatic relations between the two countries–a figure that grows to 88% among those younger than 30. “It’s 2015,” says Julia Diaz, a Cuban American who left Cuba for Florida in 1970 at age 10. “We need a new approach.”

More than half a century of diplomatic and economic isolation by the U.S. has had virtually no success in changing the politics of Cuba. The 88-year-old Fidel outlasted 10 American Presidents and his patrons in the Soviet Union before handing power to his younger brother Raúl in 2011. The embargo may have helped keep Cubans poor, but it likely enhanced the Castros’ stature in Latin America, especially since Cuba has long ceased any real effort to export its creaking communist revolution abroad. The gleefully anti-American Venezuelan President Hugo Chávez took great pride in propping up his ideological allies in Havana, providing Cuba with most of its oil and billions of dollars in aid–a small price to pay for sticking his finger in Washington’s eye.

But Chávez died in 2013, and today Venezuela’s oil-dependent economy is all but collapsing thanks to the plummeting price of crude. Realizing that there’s no guarantee of future support from Venezuela may have made Raúl Castro “much more eager to negotiate and would have given the U.S. leverage,” says Ted Henken, a Cuba expert at Baruch College in New York City.

For Obama, the thaw should improve the U.S.’s standing in a region that has shifted away from the leftist policies of Cuba and Venezuela in recent years but is still sensitive to any bullying from Washington. “It’s going to be a lot easier for other U.S. allies in the region to swing away from Venezuela,” says Christopher Sabatini, the senior director of policy at the Council of the Americas.

In Havana, bells tolled in celebration when Raúl Castro announced the policy shift, which will have a much bigger impact on Cuba than it will on the U.S. Raúl has taken baby steps toward a freer market: Cubans are now allowed to buy and sell property, and nearly 500,000 are self-employed. Obama’s new policy could allow a flood of capital into Cuba, whose economy is expected to grow by just 1.3% this year, according to Cuban government statistics, despite the recent economic reforms.

With Raúl set to step down in 2018, the regime has made a calculation that allowing greater openness will help the country manage that historic transition–and its old enemy can help. “That will happen better and faster with a normal diplomatic and political relationship with the U.S.,” says Sweig.

But Americans shouldn’t be planning their retirement condos on the Cuban coast yet. Change won’t come overnight. “Business will only succeed if the Cubans want business to succeed,” says Gutierrez. “They need to demonstrate that it is different.” While Raúl said in his speech that Obama “deserves the respect and acknowledgment of our people,” he made it clear that he wants much more. “The economic, commercial and financial blockade,” he said, “which causes enormous damages to our country, must cease.”

That’s not something Obama can do on his own. The embargo is codified into U.S. law. While the President can modify the implementation of the embargo, it would take an act of Congress to lift it altogether. Any U.S. ambassador in Havana would also need approval by the Senate. Rubio–who sits on the Senate Foreign Relations Committee–has made it clear he’ll do whatever he can to prevent that. “This Congress is not going to lift the embargo,” he told reporters after Obama’s speech. He may not have the final word. It’s worth noting that Senator Rand Paul, one of Rubio’s potential opponents for the 2016 Republican nomination, came out in favor of normalizing relations.

Cuba is still an autocracy, and the Castro regime has decades of human-rights abuses to answer for. But the Castros aren’t the point. For over 50 years the relationship of these two countries–“at once family and foe,” as Obama put it–has been as fixed in the past as the 1950s Chevrolets that putter through the streets of Havana. On Dec. 17, the U.S. and Cuba made history by finally looking to the future.

–WITH REPORTING BY GIRISH GUPTA/CARACAS, LORI ROZSA/MIAMI AND ELIZA GRAY/NEW YORK

This appears in the December 29, 2014 issue of TIME.

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