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A magnet of President Obama smelling a cigar hangs with magnets of Che Guevera in a tourist booth in Old Havana.Deborah Baic/The Globe and Mail

With its vast menu of high-end diner food, waitresses in fifties-style miniskirts and ESPN2 playing on huge HDTV screens, La Chucheria is a restaurant that diners would expect in Miami's Little Havana, but not in Havana itself.

Located far from the tourist areas, (but not so far from the still-operational hotel that gangster Meyer Lansky used to own), the bright and boisterous La Chucheria improbably exists in the land of the Castro Brothers. It's one of many encouraging green shoots of private ownership I saw amid much dreamy dilapidation. But there are uncomfortable reminders of political sensitivities. The restaurant management, which has two locations with more apparently on the way, is very jittery about speaking to me about Raul Castro's economic reforms and its own success. It doesn't want any news interviews taking place on its property. The optics, I suspect, wouldn't be good. I sneak the occasional note and whenever possible hide the notebook.

As U.S. Assistant Secretary of State for Western Hemisphere Affairs Roberta Jacobson arrives in Havana Wednesday to discuss diplomatic recognition with her Cuban counterparts, you get the sense that if normalization between the two countries happened tomorrow, there would still be a few cultural and economic obstacles. But both Raul Castro and Barack Obama need this thaw to happen. Which might explain why the two sides have taken their frigid diplomatic relations and stuck them in a microwave.

There are decades – and some would say more than a century – of historical baggage to unpack. At the same time, there is the constant reminder that these countries are closer apart than 145 kilometres of distrust and 60 years of enmity that separate them. The first song heard upon arrival, in the cab from the airport, was Meghan Trainor's All About That Bass. At La Chucheria, my guest reminds me that Cubans love reruns of Seinfeld, Grey's Anatomy and House.

Ms. Jacobson's touchdown on Cuban soil Wednesday helps mark the denouement of one of the world's most bitter feuds, which intensified in the early 1960s with John F. Kennedy and Fidel Castro – two heads of states whose industrious affection for beautiful women and Cuban cigars did little to bridge vast and implacable ideological differences.

For the United States, after all, it was an era of Camelot in Life Magazine and a fear of the grinding inhumanity of Communism in the USSR and China. For Cuba, it was a continuation of shaking off the Yanqui shackles and rebellion against its domination. Over the next six decades, the mutual vilification between the United States and Cuba gave rise to near-apocalyptic military misadventures, soaring polemical rhetoric, a punishing embargo and egregious human-rights violations.

Cubans are as shocked by the new era of détente as Americans. Experts here admit that President Obama's December announcement took them off guard, even though there were signs – more conciliatory language from Cuba at the United Nations, repeated calls for engagement in New York Times editorials. They are also astounded by the speed at which diplomatic recognition, and perhaps normalization, is unfolding.

Even the propaganda posters around Havana imploring the United States to release five of its citizens – intelligence officers known as the "Cuban Five" – feel dated. That was so one month ago. It's already happened. The city's intelligentsia has moved on, perhaps, buzzing about visits from a U.S. delegation on the weekend. The six-member delegation of congressional Democrats, led by Senator Patrick Leahy, met Foreign Minister Bruno Rodriguez as well as dissidents and Cardinal Jaime Ortega during its two-day visit.

Like many Americans, experts here believe Mr. Obama's move toward rapprochement is motivated by his lack of a diplomatic legacy. Unlike other rogue regimes the United States is trying to negotiate with, Cuba is an easy win, political scientist Rafael Hernandez told me in his darkened living room, tipping in on his rocking chair. "We are angels compared to the Iranians," said Mr. Hernandez, who also is the editor-in-chief of Temas, a glossy social-science quarterly. "With Cuba, it is much easier."

Mr. Hernandez added there is urgency for both sides to ink a deal. There is a two-year window for Mr. Obama to sow his legacy that he introduced to the world last month, and for Cubans to push talks far enough along that a Republican who may take office in two years can't roll relations back to another era.

From Cuba's point of view, warmer relations would also help relieve Cuba's siege mentality, opening up their privatization reforms to a wider pool of investors and helping liberalize an economy that is hobbled by statist bureaucracy and left without its most recent patron, Venezuela, a petrostate that has fallen victim to low oil prices.

Ms. Jacobson will be the first official from the State Department to visit Cuba since the Jimmy Carter era, a historical bread trail that Mr. Obama's critics would no doubt find delicious. The President's critics see détente with Cuba as craven and self-serving, an effort to solidify his sorry foreign-policy credentials at the expense of Cuban human rights and U.S. values.

They also worry that their country is giving away everything without first winning concessions from Cuba. "This is a windfall for the Castro regime that will be used to fund its repression against Cubans, as well as its activities against U.S. national interests in Latin America and beyond," said Marco Rubio, the Cuban-American senator from Florida, last week.

For Mr. Obama, however, it wouldn't just be a rare win with Cuba. It would elevate the image of the United States in Latin America, and at home, represent a shrewd political strategy. In effect, political analysts say, normalization would split the GOP down the middle. There will be the Miami anti-Castro crowd and also the Wall Street Republicans, who will see a business opportunity and wonder why only the Chinese and Europeans are getting in on the action. "Obama's laid a poison pill for whomever the Republicans nominate," said Michael Kelly, a noted Cuba expert and international law professor at Nebraska's Creighton University. "You can't win election without carrying Florida."

A recent discussion about the location of a future Cuban consulate underscores just how complicated the Sunshine State is. Miami, where almost a million residents have Cuban ancestry, has always been militantly anti-Castro. If diplomatic relations were normalized, the city's leaders say they wouldn't want a Cuban consulate. Near the state's west coast, however, there is Tampa, whose mayor and chamber of commerce have been lobbying the Cuban leadership for a consulate for more than a decade.

While consular representation is likely one item on Wednesday's agenda, migration is supposedly at the top. One sore spot for the Communist island has been the Cuban Adjustment Act. Enacted in 1966, the U.S. law offers Cuban expatriates a swift route to U.S. residency once they touch American soil. Officials here resent the act. To begin with, it inherently encourages defection, they say, but officials also contend it lures immigrants across the perilous Florida Straits, perpetually creating a potential humanitarian crisis.

As part of diplomatic recognition, the two sides are expected to discuss the reopening of their embassies, a development that would also likely allow each of their diplomats to go further than the 40 kilometres from their host cities currently permitted. Flight travel is also a likely topic. The rules announced last Thursday allow U.S. travellers to book travel to Cuba directly with a U.S. carrier, rather than through selected charter companies. This change, however, will require a civil-aviation agreement to create rules for taxes, fees, customs and security. "The Obama administration will do as many things as they can as an indication of good will," said Mauricio Tamargo, a legal expert in U.S. land claims at the Washington firm Poblete Tamargo. "Travel and remittances. Easy things."

Normalization, experts say, will be more difficult. One elephant in the room is settling around $7-billion (U.S.) in U.S. land claims. Almost 6,000 claimants are looking for compensation for property they say Fidel Castro's government confiscated when it took power. Unlike the Cubans who left the country when the Communists took power, these claimants were already abroad and according to international law, eligible for remuneration.

The largest holder is Office Depot, which through a serpentine history of mergers and acquisitions inherited the claim for the Cuban Electric Co., which in 1960 supplied more than 90 per cent of all the electricity sold on the island. Already there is a call for creativity from both sides to settle the issue, whether it is joint-ventures or land swaps. "We're not Qatar," one Cuban political scientist told me. "We don't have that money in a drawer."

Not to be outmanoeuvred, Cuba has its own law regarding compensation, which demands that the United States pay for the damage the economic embargo wrought on its land. "We do not believe those things would be resolved before diplomatic relations would be restored, but we do believe that they would be part of the conversation," Ms. Jacobson has said.

In the meantime, perhaps a few Seinfeld references will ease the tension.


What has already changed

  • U.S. and Cuba released prisoners
  • U.S. eased travel restrictions for U.S. citizens

What Cuba wants

  • Lifting of the U.S. trade embargo
  • Removal from the U.S. State Department list of states that sponsor terrorism

What the U.S. wants

  • Return of U.S. fugitives living in Cuba
  • Free travel in Cuba for U.S. diplomats
  • Free access for Cubans to U.S. embassy
  • Settlement process for confiscated property claims

Editor's note: An earlier version of this story misspelled the name of Havana's La Chucheria restaurant.