According to an article published online late Wednesday by Newsweek, consultants at Seven Arrows Investment and Development Corp. traveled to Cuba in 1998 on behalf of a casino company Trump used to own. Trump's company then reimbursed the consultants for $68,000.
"The goal of the Cuba trip, the former Trump executive says, was to give Trump's company a foothold should Washington loosen or lift the trade restrictions. ... The former executive says Trump had participated in discussions about the Cuba trip and knew it had taken place," according to the story.
Newsweek reported that the spending apparently violated U.S. law at a time when a decades-long embargo against Cuba was still tight.
The allegations about could play into one strand of criticism leveled at Trump, namely that the real-estate mogul seems comfortable dealing with autocrats and dictators.
Trump's campaign manager, Kellyanne Conway, took a stab at damage control Thursday on The View. Conway emphasized that the article said Trump did not ultimately decide to invest in Cuba, and she tried to pivot to questions about whether the actions of Trump's Democratic opponent, former Secretary of State Hillary Clinton, were influenced by contributions to her family's foundation.
"He's very critical of Cuba," Conway said of Trump. "He's very critical of Castro. ... We're talking about did his hotel invest money in 1998 in Cuba? No. Did she get money from seven foreign governments while she was secretary of state? Yes. And somehow that's not relevant. It's very relevant to me."
The allegations about the 1998 trip could play into one strand of criticism that the Clinton campaign has leveled at Trump, namely that the real-estate mogul seems comfortable dealing with autocrats and dictators. But potential dealings with Cuba could be particularly damaging in Florida, where Miami's Cuban-American exile community has long been a crucial voting bloc for Republican hopefuls.
The Florida Democratic Party pounced and suggested Trump wasn't the only Republican who would have to deal with the allegations in November. Party Chairwoman Allison Tant specifically called out U.S. Sen. Marco Rubio, R-Florida, a son of Cuban immigrants who ran against Trump in the GOP presidential primary but has since endorsed him.
"The meek excuses from Marco Rubio and Florida Republican leaders must come to an end: Donald Trump is dangerously unqualified to be president and his foreign business interests pose unprecedented conflicts of interests," Tant said. "Marco Rubio was right when he called Donald Trump a con artist. It's time for Florida Republicans to admit they've been conned."
For his part, Rubio seemed to be laying the groundwork to criticize Trump depending on how the campaign handles the allegations.
"I hope the Trump campaign is going to come forward and answer some questions about this, because if what the article says is true – and I'm not saying that it is, we don't know with a hundred percent certainty – I'd be deeply concerned about it. I would," Rubio told the ESPN/ABC "Capital Games" podcast.
Even before Trump, there have been signs that the GOP is losing its longtime hold on the Cuban vote in Florida, as second- and third-generation Cuban-Americans feel fewer connections to the island and become more liberal generally.
Exit polls by Bendixen & Amandi International, a Miami-based research and consulting firm, and a study by Dario Moreno, a political science professor at Florida International University, found that 2012 Republican presidential nominee Mitt Romney got what Moreno called "historically low support among Cuban-Americans in Florida."
The Trump allegations could give older Cubans a reason to abandon Trump as well.