Obama had announced in December 2014 that he and Castro were restoring ties and less than a year later, the US Embassy in Havana was re-opened with the then US president making a historic visit to the Communist country in 2016.
But facing pressure from US businesses and even some fellow Republicans to avoid turning back the clock completely in relations with communist-ruled Cuba, the Republican president chose to leave intact many of his Democratic predecessor's steps toward normalization. "They will not manage to weaken the Revolution, nor defeat the Cuban people".
It's for the Cuban people to decide whatever changes are necessary in the island.
Critics of the President's decision, however, note that the USA has a relatively friendly relationship with other countries with poor civil rights records, including Saudi Arabia, where Mr Trump travelled to during his first foreign trip in office.
Earlier Friday, Trump vowed to overhaul Obama's policies. He characterised the administration of Raul Castro as a "brutal, brutal regime", and spoke with a flourish describing the brutal crackdown and imprisonment of religious worshippers in the island country. The officials spoke on condition of anonymity to discuss the policy before Trump announces it, despite the president's regular criticism of the use of anonymous sources.
The statement said a "strategy aimed at changing the political, economic and social system in Cuba, whether it seeks to achieve it through pressures and impositions, or by employing more subtle methods, will be doomed to failure".
During a speech Friday in Miami, Trump portrayed his updated policy as the fulfillment of a campaign promise to reverse Obama's diplomatic rapprochement with Cuba after decades of estrangement.
Trump cast that as a sign the USA still wanted to engage with Cuba in hopes of forging "a much stronger and better path".
"We will not lift sanctions on the Cuban regime until all political prisoners are freed, freedoms of assembly and expression are respected, all political parties are legalised and free and internationally supervised elections are scheduled", Trump said. Obama eliminated the tour requirement, allowing tens of thousands of Americans to book solo trips and spend their money with individual bed-and-breakfast owners, restaurants and taxi drivers. However, the policy will allow USA businesses already engaged with Cuba to continue doing business.
The changes will not go into effect until regulations are drafted by the US Treasury Department and other agencies, officials said. This will essentially shield US airlines and cruise lines serving the island. "And we are going to be safeguarding those people", he said. "I do think you're likely to see a fewer number of flights and higher fares", said Andrew Keller, a partner at Hogan Lovells focusing on worldwide trade and investment.
Targeting payments to the Cuban military will have an impact on the tourism industry because of the military's vast involvement in the broader Cuban economy, including through ownership of the Gaviota hotel chain.
Lee said it will hurt American jobs created through eased restrictions and private Cuban businesses.
But "personally, part of what makes it hard [to accept] is that we were six years into the administration and spent a year and a half of exhaustive negotiations before announcing" the Cuba opening, said Rhodes, who coincidentally spoke at a Cuban entrepreneurship event in Miami on Monday.
He alleged that for almost six decades, the Cuban people had suffered under the Communist domination.
The policy change once again raised questions about whether or not Trump has done enough to separate his business interests from his public office.