Among those attending Raúl Castro’s Dec. 20, 2014 speech in Havana were Elián González and two of the intelligence agents known as the “Cuban 5”: Fernando González, bottom left, and René González, bottom center. (Enrique De La Osa/Reuters)

Critics of President Obama’s move to normalize relations with Cuba insist it will deliver big rewards to the island’s military-led government, which controls as much as 80 percent of the economy.

They are almost certainly correct.

The bigger question, though, is whether Obama’s initiatives can position the United States to more effectively influence events in Cuba on the day the country is no longer run by someone named Castro.

If the overarching goal of the old U.S. policy was to precipitate a collapse of the Communist government, Obama’s new approach reflects a conclusion that such instability is no longer in the best interests of the United States.

With the announcement last week, Washington acknowledges that, like Havana, it wants a managed, orderly transition to a post-Castro future. What that future will look like is the game going forward.

“Do we want a hard landing or a soft landing?” Arturo Valenzuela, who served as assistant secretary of state for Latin America during Obama’s first term, asked in an interview. “It’s not in our interest nor in the interest of the Cuban people to see a total collapse.”

Raúl Castro, 83, has repeatedly said he will step down from the presidency in 2018. There has been speculation that he might leave early, while he’s still in relatively good health. Among his possible successors are Vice President Miguel Díaz-Canel, 54.

In an address to Cuba’s parliament Saturday, Castro set April 2016 as the date for a new Communist Party Congress — an event that has served in the past as the occasion for reform announcements and leadership changes. The last one, in 2011, was the first of its kind in 14 years.

In the audience was 21-year-old engineering student Elián González, who as a child survived the wreck of a boat headed to the United States and became the object of a drawn-out custody battle that eventually saw him return to Cuba. There, too, were the long-imprisoned, lionized intelligence agents known as the “Cuban 5,” the last three of whom were freed in the deal with Obama.

Fidel Castro, 88 and ailing, was not there.

In his speech, Raúl Castro reiterated a willingness to talk about a broad range of issues with Washington but said that Cuba’s one-party state and its socialist principles were not up for discussion.

“Just as we have never proposed to the United States to change its political system, we will demand respect for ours,” he said.

He and his close circle of aging guerrilla fighters look to Vietnam, not China, as a model. With a relatively open market economy, a thriving tourism industry, and the Communist Party firmly in charge, Vietnam appears to the Cubans as a symbol of Marxist prosperity.

Vietnam, too, was once a bitter enemy of the United States. Now the former foes do $30 billion a year in trade.

Obama’s critics have pointed out that sneaker and sports apparel factories haven’t brought liberal democracy to Vietnam.

But the president argues that a closer relationship with Cuba will give the United States more leverage over the island’s future.

“We will be in a position to respond to whatever actions they take, the same way we do with a whole range of countries around the world when they do things we think are wrong,” Obama said in a news conference Friday. “There may be carrots as well as sticks that we can then apply.”

It remains to be seen whether Cuba’s leaders are ready for that type of engagement. They bristle at talk of carrots and sticks, which sounds to them like something for farm animals, not diplomatic equals.

U.S. brands and companies are held in high esteem on the island, where countless 1950s-era Chevrolets, Westinghouse refrigerators and other products from the golden era of American manufacturing remain in use. But firms from Europe, Canada and Latin America have a 20-year head start in the Cuban market, partnering with the government on tourism megaprojects, mining investment and petroleum. Brazil is helping Cuba build a $1 billion port facility and industrial hub at Mariel, the place from which more than 100,000 Cubans fled in the famous 1980 boatlift.

Cuba wants more foreign investment, and it has already revised its 2015 economic growth projections upward on the assumption that the American thaw and a boom in U.S. tourism will attract a surge of outside capital.

But the country’s investment laws fall far short of international norms, and the government exercises tight controls on the hiring of Cuban workers.

U.S. officials have tempered their sweeping Cuba announcement by cautioning that it is unrealistic to expect the island to change too rapidly. Still, they say their Havana counterparts are eager to move quickly on the agenda mapped out by Obama and Castro.

Carl Meacham, who was a senior adviser for Latin America and the Caribbean on the Senate Foreign Relations Committee, likened the process of reestablishing relations to turning around an aircraft carrier, a move that will begin to generate its own momentum. “The hard work of diplomacy begins now,” he said.

“This is a policy shift from isolation to engagement,” said Meacham, now Americas director at the Center for Strategic and International Studies. “If there are issues with human rights, you can talk about them directly, in an explicit way.”

A cautionary example

Russia’s post-communist transformation has served as a cautionary example of the type of transition the United States would like to avoid 90 miles from its territory.

The Cuban government and its array of state-run enterprises in tourism, mining, banking and retail operate with a high degree of opacity, and many are controlled by the military — a necessity, the Castros have insisted, because of unyielding American hostility. It is not clear whether the economic system will provide a more open climate for businesses in coming years.

A frequent theme in Raúl Castro’s speeches as president has been Cuba’s creeping culture of corruption, which he calls one of the country’s “greatest enemies.” A few high-ranking officials and foreign businessmen have been jailed for graft. But Cubans who have survived for decades on meager salaries by pilfering goods and hustling tourists for hard currency are highly adept at evading the rules to get by.

U.S. officials worry that this type of culture could morph into something more worrisome after the Castros leave power, turning the island into a haven for organized crime figures far more sinister than the ones chased off by the bearded rebels in 1959.

A rapid unraveling of the highly centralized state and security apparatus could also send a wave of migrants to U.S. shores.

Having a better footing in Havana will give the United States a better shot at avoiding these scenarios, diplomats say.

“Will they emerge out of this as a country based on the rule of law?” said Valenzuela. “Cuba could become a democracy, or it could turn into a kleptocracy like the Russians.”

Just as multiparty democracy isn’t around the corner for Cuba, the return of American companies to the island is also far from imminent. Kennedy-era U.S. trade sanctions can only be unlocked by Congress. So even as Obama pokes holes in the embargo for things like cigars, ATM cards and farming equipment, regularized trade relations remain distant.

Vigorous internal debate

After 55 years of Castro rule, the vast majority of the island’s 11 million residents know no other leaders. But whoever follows the brothers will likely try to derive his political legitimacy from his proximity to the Castros and their vision for Cuba’s future.

The struggles of Venezuelan President Nicolás Maduro, the successor to populist president Hugo Chávez, show that can be a shaky strategy.

Behind the facade of unanimity in the Cuban Communist Party, there is a vigorous debate between reformers who want a faster pace of change and hard-liners who hold back, either out of self-interest or a lifelong fear that the United States and Miami exiles will never stop plotting to squash them.

Moderate voices in the country’s nascent civil society say they will use the Obama-Castro rapprochement to try to bridge political divisions with a renewed sense of Cuban nationalism.

Cuba Posible, a group that includes writers affiliated with the Catholic Church and several other prominent intellectuals, said in a statement Thursday, “We’re aware that it will not be a political process free of tension, and it will unleash a polarization among different groups, within Cuba and outside it.”

The group promised to work at building consensus on the principles of what it called “national sovereignty and citizenship, responsible freedom and social justice, hope and solidarity, an economic vision of development and the common good, a defense of the most vulnerable and a commitment to non­violence.”

Many Cubans, including some whose feelings about the Castros and their revolution are far messier than the public debate would suggest, have said what impressed them most about Obama’s gesture last week was how he seemed for the first time to be speaking to them as equals.

This was the same theme — Cuban nationalism — that Fidel Castro appealed to 55 years ago in his rise to power, before the island’s rupture with the United States and before he took his country in a far different direction.