Jeffrey DeLaurentis, Obama's nominee, currently serves as the US charge d'affaires in Cuba. Despite his qualifications, DeLaurentis is unlikely to receive the promotion because senators opposed to Obama's Cuba opening are unlikely to approve his nomination.
It is the latest example of American moves laden with symbolism that don't always translate into on-the-ground changes for the island just 90 miles from the Florida Keys, though the US president and his policy remains popular even so.
Cuba residents expected the renewed ties with the US would help improve their quality of life, but more than a year after the formal resumption of relations, many told CNN that they feel not much has changed.
There have been moves toward improving economic ties between the two countries, and earlier this month the first commercial flights resumed between the US and Cuba. But Obama's call for Congress to lift the US embargo against Cuba hasn't been successful.
When Obama made a historic visit to the Communist country in March, many in the US and Cuba hoped it would be a catalyst for the government to grant more freedoms to its people and open the doors for American businesses in the country.
"When (Obama) was here, we were yelling happily, 'Obama! Obama!,' as if we were excited he was visiting us," a Cuban told CNN in Spanish. "What we really meant was, 'Obama! Help us!,' because we want more freedom like Americans."
This middle-aged man, like most Cuba citizens who spoke to CNN, said he didn't want his name to be included in a story in the US media for fear of a backlash from his government.
Most Cubans who did agree to speak anonymously had only positive things to say about Obama.
"When he visited, that was a big deal and important to the country. Everyone paid attention," one teenage girl told CNN.
Sebastián Arcos, associate director of the Cuban Research Institute at Florida International University, told CNN that Cubans are looking forward to the future because of the improved relations between Havana and Washington.
"They see (the changes) with optimism. For a simple reason: They've been told that the problems in Cuba are a result of the hostility of the United States," he said. "When the President says there's no longer any hostility, they are optimistic about the change."
Many Cubans blame the embargo that essentially prohibits any business with America as one of the reasons for their lack of economic prosperity -- and they hope it will be lifted soon.
Arcos said another reason Obama is beloved by Cubans is because of his race.
"Obama is a black president to a white population. And Raul Castro is the white leader to a brown population," he said in a phone interview. "They wish they had a leader who looked like them -- the way Obama looks."
Several Cuban citizens told CNN they feel there are similarities between their culture and America's, including their mutual enjoyment of sports such as baseball and Hollywood movies (because of the challenges the embargo poses to importing new productions, Cubans referenced '90s flicks such as "Saving Private Ryan" and "Braveheart").
One Cuban citizen who declined to give his name shared his experiences as a government worker in Havana making only $20 a month yet trying every day to make a decent life for himself and his family.
"People who live in the United States are lucky," he said in Spanish. "They can work very hard, save their money, buy a plane ticket and leave. We work hard, save our money -- but we can't afford to buy a plane ticket and leave."
He also said he respects Obama as the leader of the United States, saying he's the leader they wish they had.
Obama will soon be leaving office, though, which could mean an uncertain future for the budding US-Cuban relationship
Still, Cubans didn't express strong opinions or interests about the 2016 presidential race between Democrat Hillary Clinton and Republican Donald Trump.
"Yeah, we'll see things about the election, but we don't really have an opinion about it," a train operator told CNN. "People side more with Clinton because she's liberal. That's about it."
Arcos said that Cubans are leaning toward the former secretary of state over the billionaire businessman mostly because of Clinton's shared policies with Obama.
"The Cuban propaganda machine is promoting Hillary Clinton," he said. "Whatever they are telling Cubans about the election is filtered, but that's usually the message."
Clinton is the first major presidential candidate to advocate lifting the US embargo on Cuba.
In Miami last year, she called for the trade blockage to end: "The Cuba embargo needs to go, once and for all."
Trump, in comparison, has recently vowed to roll back the improved relations with Cuba until the island's leaders improve their record on human rights
Last September, however, Trump told the Daily Caller that he's okay with normalizing relations with Cuba.
"I think it's fine. I think it's fine, but we should have made a better deal. The concept of opening with Cuba -- 50 years is enough -- the concept of opening with Cuba is fine," Trump said. "I think we should have made a stronger deal (with Cuba)."
Earlier this month, Trump shifted his stance, saying he would reverse the arrangement President Barack Obama struck to reopen diplomatic relations and reestablish some trade with Havana unless the Cuban government meets his demands to restore political freedoms and free political prisoners.
"All of the concessions that Barack Obama has granted the Castro regime were done with executive order, which means the next president can reverse them. And that is what I will do unless the Castro regime meets our demands," Trump said on September 16.
Whether or not the embargo will be completely lifted under a future US administration remains to be seen. But Cubans continue to hope.
"I look forward to the future," one Cuban told CNN in Spanish. "And I have confidence that the worst is behind us."