Eduardo Clark holds American and Cuban flags across the street from the Cuban embassy in Washington, D.C., U.S., on July 20, 2015. 
Photo by Andrew Harrer/Bloomberg/Getty

Donald Trump’s Cuba problem comes with big risks

The Rachel Maddow Show, 9/28/16, 9:00 PM ET

New article to look at Trump ties to Cuba during embargo

Rachel Maddow shares an exclusive sneak peek at a new Kurt Eichenwald article in Newsweek that will examine Donald Trump’s business ties to Cuba when the U.S. embargo was still in place.
The Newsweek cover story Rachel discussed at the top of last night’s show is a doozy: investigative reporter Kurt Eichenwald, citing internal company records and court filings, reported that Donald Trump “secretly conducted business” in Cuba, spending $68,000 through a consulting firm to explore a business venture on the island.

If accurate, the allegations raised in the report are problematic for all sorts of reasons. First and foremost, it would have been illegal for Trump’s enterprise to spend money in Cuba under a U.S. economic embargo. There are also political considerations, given that many Cuban Americans in South Florida would not be pleased to learn Trump illegally spent this money, as alleged.

Complicating matters, Trump was on record defending the economic embargo at the same time he was reportedly violating it, according to the Newsweek article.

Today, Trump’s campaign manager made a television appearance in which she appears to have made the story quite a bit worse for her boss. The Washington Post noted:
Donald Trump’s campaign manager denied Thursday that one of the GOP nominee’s businesses violated the U.S.-Cuban embargo in 1998, dismissing an investigative report that accused Trump of knowingly spending $68,000 staking out an investment on the island.

“Read the entire story. It starts out with a screaming headline, as it usually does, that he did business in Cuba. And it turns out that he decided not to invest there. I think they paid money, as I understand from the story, in 1998 – and we’re not supposed to talk about years ago when it comes to the Clintons,” Trump’s campaign manager, Kellyanne Conway, said on ABC’s “The View” Thursday, amid cross talk.
Conway emphasized repeatedly that Trump ultimately chose not to follow through on the Cuban venture. By all appearances, that’s correct. But the question is whether Trump spent $68,000 in Cuba in 1998, as the report claims, in violation of the U.S. embargo.

And on that front, Conway said this morning, “I think they paid money, as I understand from the story, in 1998.” Trump’s campaign manager may not have intended to be quite so candid: she effectively endorsed the point of the Newsweek article she hoped to dismiss.

Indeed, the Trump campaign also issued these talking points to surrogates today, trying to offer a defense of the candidate’s alleged efforts in Cuba, and there’s literally nothing in the talking points that refutes any of the concerns raised in the piece.

In other words, if Team Trump has found any factual errors in Eichenwald’s Newsweek reporting, the campaign hasn’t identified those mistakes to anyone else.

Not surprisingly, Hillary Clinton’s campaign has taken a keen interest in the story. Senior policy adviser Jake Sullivan released a statement this afternoon that read: “Trump’s business with Cuba appears to have broken the law, flouted U.S. foreign policy, and is in complete contradiction to Trump’s own repeated, public statements that he had been offered opportunities to invest in Cuba but passed them up. This latest report shows once again that Trump will always put his own business interest ahead of the national interest – and has no trouble lying about it.”

Some Republicans have concerns of their own. Sen. Marco Rubio (R-Fla.) said this morning that Trump and his team are “going to have to give a response to” these questions.

The senator, who is himself a Cuban American from South Florida, added during an ESPN/ABC Capital Games podcast interview, “I mean, it was a violation of American law, if that’s how it happened. 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 100% certainty – I’d be deeply concerned about it. I would.”

Cuba, Donald Trump and Marco Rubio

Donald Trump's Cuba problem comes with big risks