Doing business with Cuba has been historically tricky, with complex U.S. rules to untangle, lack of direct bank transactions and an often unreceptive Cuban government.
President Raúl Castro's retirement next week — marking the first time in nearly 60 years Cuba will be ruled without a Castro — was long expected to pave the way for increased business between the U.S. and Cuba.
But, as it turns out, it may not make much of a difference. Recent policy changes under President Trump and a series of standoffs between Washington and Havana have made that process thornier than ever.
More from USA Today:
Cuba will soon be without a Castro as leader for first time in nearly 60 years
Cuba, once bustling with heavy-spending Americans, sees steep decline in U.S. travelers
Stock market wavers after Trump tweets about Syria strike and tensions rise with Russia
"The climate has certainly changed," said Jay Brickman, vice president of Jacksonville-based Crowley Maritime Corp., which transports shipping containers full of chicken from Florida to Cuba. "The optimism that was there has been dampened. People are investing less time to see how they could enter the Cuban market until they see where the relations are going."
When the two former Cold War foes announced warmer relations in December 2014, U.S. businesses were hopeful they could start doing business with Cuba, just 90 miles away. Policy changes under President Obama encouraged Americans to travel to the island and seek out business opportunities.
But Obama's changes didn't go far enough to undo restrictions under the U.S. embargo against Cuba, provisions in place since 1960 that severely restrict doing business with the communist island, said John Kavulich, president of the U.S.-Cuba Trade & Economic Council, a New York-based non-partisan business group that provides information and analysis on doing business in Cuba.
On the flip side, the Cuban government also resisted opening up Cuba too much to private enterprise, he said. In August, it placed a temporary halt on new licenses for bed-and-breakfasts, restaurants and other privately owned businesses. Last year, it balked on an offer by Google to expand Internet across the island through Wi-Fi connections and cellphones.
"They're skeptical," Kavulich said. "The re-emergence of the United States' presence in Cuba is, by definition, disruptive and uncertain."
Since taking office, Trump has unraveled some of Obama's historic changes, including barring Americans from providing money to certain Cuban businesses run by the military and doing away with "people-to-people" visas that thousands of Americans used recently to travel there.
Last year, relations took a sharp turn for the worse when U.S. officials accused Cuba of "sonic attacks" on U.S. diplomats on the island. In September, the State Department issued a travel advisory warning Americans not to travel to Cuba in lieu of the mysterious attacks. It downgraded the notice four months later.
And in February, a task force ordered by Trump announced it was brainstorming ways to expand Internet access and improve access to information on the island, despite a formal protest by the Cuban government, which viewed it as an attack on Cuban sovereignty.
All this has had a chilling effect on U.S. travel to Cuba and business prospects between U.S. and Cuban companies, said Richard Feinberg, a senior fellow at the Brookings Institution and author of Open for Business: Building the New Cuban Economy.
"The hopeful scenario was that with the Castro brothers either gone or in the background some of the vile in U.S.-Cuba relations will have been drained," he said. "But I don't see any interest in improving U.S.-Cuba relations in the short term."
Brickman, the shipping executive, said he hears the concerns from his Cuban counterparts when he travels to the island on business. Cuban officials and business leaders want to know how the Trump administration will impact long-term relations with the island.
The new developments haven't hurt his current business but his firm, like others, has put on hold any expansion plans in Cuba until relations stabilize, Brickman said.
Meanwhile, Cuba, with the economy of ally Venezuela in free fall and prospects for improved relations with the U.S. dim, will look to other countries, like Iran and China, for help, he said.
"If the U.S. door for right now is not as open, perhaps there are other doors with more benefits for them," Brickman said.