Faced with sorting out nearly six decades of financial claims and counterclaims against one another that run into the hundreds of billions of dollars, diplomats from the United States and Cuba resorted on Tuesday over one of the most contentious issues remaining between the two countries. The two sides are sitting down for the first time to discuss the American properties Cuba confiscated decades ago.

U.S. citizens and companies say they're owed about $7 billion in property that the Cuban government seized when Fidel Castro took control of the island in 1959. The Cubans say they're owed $181 billion in damages from the economic embargo the U.S. has maintained on the communist nation for five decades. 

USA Today reports that, on Tuesday, the two sides started bridging the economic gap during a day-long meeting in Havana. A U.S. State Department official, who spoke on the condition of anonymity because of the sensitive nature of the negotiations, said the discussions were respectful and professional. The official said the two sides presented their claims and explained why they thought the money was owed.

According to The New York Times, in 1999, a Cuban court found the United States government liable for deaths and damages caused by America's "aggressive policies" against the island - namely, the Bay of Pigs invasion and the trade embargo prohibiting American citizens and companies from doing business in Cuba. Arguing that the United States had strangled Cuba's economy and caused irreparable harm, the court ordered the United States to pay $181 billion in damages.

Head of United States affairs in the Cuban Foreign Ministry, Josefina Vidal, told after the first meeting of the bilateral commission this fall that, "This is an extremely complicated subject," "I imagine that when the two countries begin to meet, one of the first things we will have to do is to clarify all the accounts."

Cuba needs the United States to lift the trade embargo, and the best way to get that done is by settling the property claims, he said. The embargo was put in place in 1962 after a dispute that began precisely because Fidel Castro expropriated American oil companies that had refused to process Russian crude.

According to Miami Herald, some analysts say President Barack Obama might have some legal wiggle room to open holes in the embargo without congressional approval, he cannot bargain away the more than $3 billion in lawsuit judgments against Cuba won by American citizens who say their relatives were murdered by Castro's security forces.

The State Department official said the two sides agreed to hold another round of talks within the next four months. The solution could end up being a mix of monetary compensation combined with changes in regulations and laws that affect each country.