(CN) - Over the past week, Assistant Secretary of State Roberta Jacobson has gone to Havana to lead the highest-level delegation from the United States to Cuba since 1977.
The talks between the United States and Cuba that commenced on Wednesday and will end on Saturday had originally been expected to involve routine migration matters. But the agenda quickly shifted following President Barack Obama's landmark speech on Dec. 17 that announced "historic steps" toward restoring full diplomatic relations with Havana.
The State Department announced that it would send Jacobson to hash out the mechanics of Obama's goals, including "technical and logistical arrangements such as embassy operations, staffing, and visa processing."
During Jacobson's trip, the State Department also promised that she would reach out to "members of independent civil society, as well as religious and independent business leaders," in still-ongoing meetings.
On Friday, three prominent Cuba watchers and professors all said in phone interviews that this week's talks marked an historic departure from past diplomacy.
William LeoGrande, the dean of American University's School of Public Affairs, noted that Jacobson is the highest U.S. official to go to Havana since the envoy President Jimmy Carter dispatched in an ultimately unsuccessful bid to normalize U.S.-Cuban relations.
As LeoGrande documented in "Back Channel to Cuba: The Hidden History of Negotiations between Washington and Havana," Carter's effort at State Department-level talks broke down after Cuba sent troops to Ethiopia at a time when the United States supported Somalia.
The secret negotiations that preceded President Barack Obama's breakthrough "will obviously go down as some of the most important ones in history because they finally changed the relationship of hostility and antagonism to one of more normal engagement between the two countries," LeoGrande commented.
But he cautioned: "It's important to point out that this is the first step in a very long journey."
Christopher Sabatini, an adjunct professor at Columbia University's School of International and Public Affairs, emphasized that this week's negotiations stand apart as having "the blessing and support of the U.S. president."
In other ways, Sabatini said he observed some fairly typical "theater" of diplomacy.
The Associated Press, for example, quoted top Cuban diplomatic official Josefina Vidal as denying Jacobson's comment that she "pressured" Havana on human rights. Vidal insisted the subject never came up.
Calling this assertion "impossible to believe," Sabatini attributed this remark to the "double-game" of statecraft.
"Diplomats are doing two things. They are negotiating with an external power, a foreign power, and they are also negotiating internally," Sabatini said.
He added later: "It was probably understood explicitly if not implicitly, 'Look, this stays in the room: You've got to say we've talked human rights; I've got to say we didn't."
Many in Havana "do not appreciate being talked down to on human rights," he noted.
Indeed, Cuban officials proposed a separate dialogue on human rights more than a year ago, and Jacobson seemed receptive to the idea at the time, LeoGrande, the American University professor, said. He pointed out that if this meeting comes to pass, the United States will not be the only party with grievances.
"We will complain about the lack of political liberties in Cuba, and they will complain about police killings of unarmed black young men and Guantanamo and I'm sure a whole long list of things they regard as human rights violations by the United States," LeoGrande predicted.
On Friday, Jacobson met with several prominent civil society and dissident groups and figures.
Cuba's first independent online news outlet, 14ymedio, quoted participants of that meeting including Jose Daniel Ferrer, a former prisoner and leader of Union Patriotica de Cuba (UNPACU); Elizardo Sanchez, founder of the Cuban Human Rights and National Reconciliation Commission; and Antonio Rodiles, a physicist and political activist who coordinates for Estado de SATS.
Baruch College professor Ted Henken, the vice-president of the Washington-based Association for the Study of the Cuban Economy, noted that some of the people Jacobson spoke to publicly criticized Obama's policy.
Demonstrating the complexity of the diplomacy, Henken noted that different representatives within UNPACU have taken different positions on Obama's policy. UNPACU's leader Ferrer perceived the shift as an "opening," and Sakharov Prize recipient Guillermo Farinas viewed it as "giving away the farm," Henken said.
The Obama State Department's policy of "principled engagement" in Cuba also helps stem criticism from Cuban-American legislators like Marco Rubio, R-Fla., and Robert Menendez, D-N.J., who use dissidents "as their shield or as their sword" against normalization, Henken said.
Speaking of Cuba's civil society leaders, Henken commented: "It is smart to listen to them, but it's also necessary to listen to them politically."
"The fact that they showed up, didn't fight with each other and then they left is a success," Henken quipped, referring generally to the week-long delegation. "Given the context and the history, it's an astounding success."
Read the Top 8
Sign up for the Top 8, a roundup of the day's top stories delivered directly to your inbox Monday through Friday.