Today's announced policy changes drew strong - and opposite - reactions from a local Cuban human rights activist and a businessman.
"It was all about this deal, by the way. From the very beginning, they arrested him for that," said Cuban-American lawyer George Fowler.
Through extremely happy to see USAID subcontractor Alan Gross home in time for the Chanukah holiday, Fowler said the trade puts Americans at risk.
"I'm unhappy for America and for Americans because all the terrorists have to do now is arrest or kidnap an American anywhere in the world, and then they know that the U.S. government, at least under President Obama, will cut a deal," Fowler said.
Fowler escaped from Cuba to the U.S. in 1960 when he was just 9 years old. He has since advocated for Cuban human rights.
"I think it weakens America," Fowler said.
Though for some, like cigar lovers, the deal comes with perks.
"They're good, don't get me wrong," said Ysidoro Rodriguez, owner of Don Leoncio Cigar Bar on Canal Street.
Rodriguez said Cuban cigars can be nearly identical to cigars from the Dominican Republic.
"Same tobacco, same taste, same watermark. Not much different," Rodriguez said.
Some cigars, such as the brand Partagas, are even made in both Cuba and the Dominican Republic. The Cuban-made cigars just have the lure of being illegal.
"Because they cannot get it regularly, like a drug, some people want it because it is illegal," Rodriguez said. "They want to try. They want to know what's going on. They want to know why it's popular."
One of the new policy changes means American travelers will be able to bring back up to $100 worth of Cuban tobacco. It's a change that Fowler argued does more to benefit Cuba than America.
"All that does is put money in Castro's pocket," Fowler said. "I don't want to do anything to put money in my enemy's hands."
As chief legal counsel for the Cuban American National Foundation, Fowler said he'll continue to fight against the relaxed sanctions and policy changes.
"Castro trades and deals with terrorists, deals with anybody who is an enemy of ours, and now we're going to do some sort of business with him and enrich him so he can continue to hurt Americans," Fowler said.