Two days after Dwight D. Eisenhower broke off diplomatic relations with Cuba on January 3, 1961, the New York Times published an editorial that both understood Eisenhower's decision but also explained that:

"All Americans and all Cubans with the interest of our two countries at heart must hope that this unhappy breach will soon be healed. It brings nothing but ill to both of us." - New York Times

The paper's calls were not heeded. Instead, it took 54 years for that breach to even begin to heal.

In December, President Barack Obama announced a policy shift toward the Caribbean island and called for an end to the current embargo. Obama, who was born in August 1961, has never personally known a time when Cuba and the U.S. had diplomatic relations.

Raul Castro, who, along with his brother, led Cuba's initial revolution back in 1961.

In this historic meeting, at the Summit of the Americas in Panama, the two leaders discussed some of the remaining issues that are stalling the restoration of relations.

One major issue is the fact that Cuba is still on the U.S.'s state-sponsored terrorism list. The state department has cleared the way for the nation to be removed, but no final decision has been made.

Cuba was first added to the list in 1982 when it was aiding other communist groups around the globe. Even though the Cold War is long over and the global battle against communism has ended, Cuba remains on the list and is subject to the subsequent repercussions.

Although the U.S. appears to be making progress on removing Cuba from the list of states sponsoring terrorism, other issues remain, including continued embargoes. One of the biggest hurdles is the Helms-Burton Act, which was passed in 1996 and strengthened already existing sanctions.

Obama also faces strong opposition from a large population of Cuban-American exiles.

Both sides, however, seem intent on moving forward with restoring relations. While Castro gave a long speech at the Summit, listing many past U.S. transgressions in the country, including supporting Fulgencio Batista and launching the Bay of Pigs invasion, he also mentioned that he did not blame Obama for this history and would continue working with U.S. diplomats to resolve lingering issues.

Obama similarly expressed enthusiasm over the historic talks as well:

"Already we’ve seen majorities of the American people and the Cuban people respond positively to this change. And I truly believe that as more exchanges take place, more commerce and interactions resume between the United States and Cuba, that the deep connections between the Cuban people and the American people will reflect itself in a more positive and constructive relationship between our governments." - U.S. President Barack Obama

Leaders throughout Latin America have praised the thawing of relations between the two countries. However, Obama's general policy toward the region has not always been popular.

In addition to worsening relations with Venezuela, the U.S. has also struggled with Brazilian relations, particularly in light of the NSA spying scandal. Many believe Dilma Rousseff and Obama still have a shaky diplomatic relationship that is slowly recovering after the breach.

Now that candidates in the 2016 field are officially entering the race, Obama is working against the clock to restore relations and generally improve U.S. ties with Latin America. He has less than two years left in his presidency, but the Summit of the Americas shows that he still has the ability -- and desire --  to make some progress.

Photo retrieved from NBCNews.com