If Fidel Castro survives through January, he will not only celebrate the 50th anniversary of his takeover of Cuba, he may also witness the most dramatic shift in U.S. policy toward the nation since it became a dictatorship.
An assortment of liberals, businessmen and farm-state politicians have been pushing for the easing of sanctions against Cuba for years, but every president, no matter the party, has done little to alter Cuba policy based on the apparent refusal to accept a totalitarian regime 90 miles from the U.S.
President-elect Barack Obama's stated position that he would like to revisit U.S.-Cuba policies has some viewing his administration as the first chance in decades to dismantle laws that restrict travel, investment, exports and cash mailings to Cuba.
"The election of Barack Obama clearly will serve as a catalyst for enhanced efforts," says Rep. Bill Delahunt, D-Mass. "I think it's a moment in time to move forward."
Not yet, others say.
Commerce Secretary Carlos Gutierrez says any weakening of sanctions will merely provide the Castro dictatorship -- Raúl Castro is the current president -- with the cash it needs to stay in power. Gutierrez says Cuba must offer reforms first or the U.S. would be giving it something for nothing.
"There's a good reason why this policy has been in place since President Kennedy," Gutierrez says. "I would be very careful before declaring that nine presidents have been wrong."
Contact With Relatives
U.S. relations with Cuba soured quickly after Castro captured Havana in January 1959. The U.S. imposed an economic blockade in 1960 and broke off diplomatic relations in 1961 as Cuba aligned itself with the Soviet Union.
A group of U.S.-trained Cuban Americans invaded the island during the botched Bay of Pigs affair in 1961, and Cuba's attempt to allow the Soviets to base nuclear missiles there threatened to start a war.
Few changes were made over the next several decades. President Clinton eased the embargo in 2000 by allowing U.S. companies to sell some agricultural and medical goods to Cuba, resulting in more than $430 million in trade in 2007.
President Bush tightened restrictions on Cuban Americans in 2004. They can visit immediate family members once every three years and cannot send relatives more than $1,200 a year.
During a May speech before a group of Cuban Americans in Miami, Obama said his strategy toward Cuba would start with lifting the restrictions on relatives. He said that Cuban Americans should be able to freely visit their relatives and that the money they send back can help them become "less dependent upon the Castro regime."
"There are no better ambassadors for freedom than Cuban Americans," Obama said.
Rep. Mario Diaz-Balart, a Cuban-American Republican from Miami, says unilaterally lifting those sanctions before Cuba changes any of its policies would send the wrong message.
"It just shows (Cuba) that you can continue to oppress people, you can continue to jail people, and the response will be, 'We'll lift some sanctions,' " Diaz-Balart says.
Easing the embargo and travel for all Americans is even more controversial.
Brooke Anderson, a spokeswoman for Obama's transition team, would not speculate on changes Obama might make to U.S. policy toward Cuba.
He could reduce restrictions placed on relatives of Cubans through an executive order. Any changes to the embargo require Congressional approval.
Jack Maybank is hoping that will happen. His Charleston, S.C.-based shipping company was the first to send a barge of U.S. goods to Havana after the embargo was relaxed in 2000.
"I'm not a politician," he says. "We are strictly business people ... and we're definitely following what the U.S. act says."
Watching what Obama will do are those on the left who believe the Castro regime is a socialism success story undermined by a hostile United States.
Toppling The Castro Brothers
Saul Landau is a fellow at the Institute for Policy Studies (IPS) in Washington, DC, which says it advises the Congressional Progressive Caucus, a coalition of left-leaning House members.
An admirer of Castro and Cuba's revolutionary "success," he says the embargo has never served its intended purpose: to hurt the Castro brothers.
"I would argue that neither Castro brother has suffered the loss of a single meal," says Landau, who said he did not speak for the IPS. "They have not been punished. The only people who have suffered have been the majority of the Cuban people."
Some policymakers say the embargo should be lifted to take down the regime.
Sen. Mike Crapo, R-Idaho, says easing the embargo and travel restrictions on Americans is the best way to topple the Castros. Crapo says an infusion of Americans and dollars would hasten the Cuban people's desire for a change.
Supporters of the embargo counter that there's no reason to think the Castros would suddenly reverse course.
Talks of ending the embargo are dangerous at a time when Cuba is realigning itself with Russia and further strengthening its ties with China and Venezuela, says Frank Calzon, director of Center for a Free Cuba, based in Arlington, Va.
"You'd like to see some sort of signals coming out of Havana that we welcome change and we're prepared to talk about this or this," says Ray Walser, a former 27-year State Department employee and a Latin America analyst at the Heritage Foundation, a conservative think tank. "You don't see any of that."