Acrimonious neighbors for 50 years, Cuba and the United States this week are expected to take the first concrete steps toward opening diplomatic relations and an entirely new relationship in trade, traffic and tourism.
The most senior American official to meet with Cuban officials in a generation is to arrive for two days of talks beginning Wednesday on normalization and immigration.
It will be a major test for both sides of their commitment and ability to move the relationship beyond the historic decision announced last month by President Obama and Cuban President Raul Castro, to the nuts and bolts and the reality.
A number of issues will be on the table: exchanging ambassadors; lifting restrictions on Cuban and U.S. diplomatic personnel in each other's country; fugitives and convicts on both sides of the 90-mile-wide Florida straits; property disputes; and financial and technological deals that will be necessary for full business interaction.
The talks "send a signal to Cuba that the [Obama] administration is taking this seriously, and it raises expectations in Cuba, and to the extent expectations are raised, that can facilitate change on the island," Tomas Bilbao, executive director of the Washington-based Cuba Study Group, said in a telephone interview.
American officials headed to the Communist-led island nation this week say they are eager and open to many possibilities but remain wary about Cuban intentions. Castro, who succeeded his brother Fidel as president, has been playing it close to the vest, welcoming the overtures of the Obama administration but declining to say how far his own government will go, and, in fact, insisting that the socialist model will remain intact.
A senior U.S. State Department official who will participate in the talks said it remained unclear what issues the Cubans will present.
"A lot depends on the willingness of the Cuban government ... a lot of the pace of [normalization] depends on ... the tolerance of the Cuban government for engagement," the official, who spoke on condition of anonymity, told reporters Monday in Washington.
The official said that aside from Castro's initial and fairly brief speeches on the new detente, as well as a spattering of other official comments, "we have seen very little in the way of signals."
Acknowledging that change will not come overnight, the official said, "It is hard to know exactly what will come out of this first conversation. … I am not oblivious to the weight of history."
The U.S. delegation will be headed by Assistant Secretary of State Roberta Jacobson, the top U.S. official for Latin America and the highest-level U.S. official in Cuba in more than 30 years.
Top on the list is the elevating of current diplomatic representations in both countries to that of a full embassy, correcting a long-standing and outdated Cold War dynamic considered fundamental to normal ties. Since the 1970s, each country had an "interests section" in the other, a reduced status and populated by diplomats not allowed to travel outside Havana or Washington.
U.S. officials will seek, in addition to the opening of an embassy, the lifting of restrictions on their diplomats' travel, the cap on the number of American diplomats allowed to be stationed in Havana, and the limit on shipments of supplies to the staff. They will also request unfettered access for Cubans who want to meet with U.S. officials, the State Department official said.
At the core of the talks, however, is the need to establish trust and communication after half a century of the opposite. It will be a precarious path, with hard-liners and naysayers in both countries eager to spoil the rapprochement.
Cuba and the United States "need to be clear they are partners for this piece of the road" even if their larger visions diverge, said Arturo Lopez-Levy, a former Cuban government intelligence analyst who teaches at New York University. "It needs to be clear they are sleeping in the same bed, even if they don't have the same dream."
Although the establishment of embassies could take place in a matter of months, and Secretary of State John F. Kerry has announced plans to visit Cuba, thornier issues like U.S. fugitives who sought refuge in Cuba decades ago, claims on property confiscated by the Castro government from citizens who fled to the U.S., and the special immigration privileges granted to Cubans by the U.S. (which the Castros claim only encourages their flight) are likely to take much longer to address.
Another major stumbling block: The U.S. continues to include Cuba on a list of state sponsors of terrorism. Obama has requested a review of that status within the next six months.
Annual reviews of Cuba to determine whether it should remain on the list have come up with steadily skimpier evidence, Bilbao said. "Including Cuba undermines the credibility of the list to begin with," he said.
Meanwhile, American companies, including the Marriott hotel chain and numerous agricultural businesses and telecommunications firms, are said to be eager to move into Cuba and tap a largely virgin market that would be inflated by arriving Cuban Americans and other tourists taking advantage of lax regulations.
Among the conditions sought when Obama announced detente, Cuba released 53 jailed dissidents. Three days later, on Jan. 15, the U.S. administration lifted a number of restrictions on trade, travel and remittances, vastly expanding the pool of American citizens who can go to the island.
The Jacobson visit follows that of a U.S. congressional delegation, whose trip to Cuba ended Monday and may have softened Cuban anxieties, although officials did not meet with Raul Castro.
Sen. Patrick Leahy (D-Vt.), a frequent visitor who was instrumental in the release of Alan Gross, jailed by Cuba and ultimately a bargaining chip, led the group and met with Foreign Minister Bruno Rodriguez. Leahy said the Cubans seemed receptive "to every single issue, from trade to communications to … agriculture."
Both countries have strong motives to make the new relationship work, experts and analysts said.
Castro desperately needs help -- foreign investment and other aid -- to salvage his economy and his gradual but real attempts at reform. The prospects of trade and new business for U.S. companies is similarly a motivating force for the U.S. government.
"It would take a major negative event to derail this process," said Theodore Piccone, a senior fellow at the Brookings Institution who studies Cuba. "There will be lots of starts and stops, but the moves on Dec. 17 [the original announcement of detente] look big enough to sustain momentum for some time to come."