Surprise! Donald Trump may have been secretly—and illegally—conducting business in Cuba in the late 1990s at around the same time he was promising Cuban Americans at home that he would never spend a dime there as long as Fidel Castro’s murderous regime was still in power. Newsweek reports that a Trump-owned company appears to have violated the U.S. embargo by paying an American consulting firm tens of thousands of dollars to make inroads in the communist country at a time when Washington was considering loosening or lifting the trade restrictions against it:

Documents show that the Trump company spent a minimum of $68,000 for its 1998 foray into Cuba at a time when the corporate expenditure of even a penny in the Caribbean country was prohibited without U.S. government approval. But the company did not spend the money directly. Instead, with Trump’s knowledge, executives funneled the cash for the Cuba trip through an American consulting firm called Seven Arrows Investment and Development Corporation. Once the business consultants traveled to the island and incurred the expenses for the venture, Seven Arrows instructed senior officers with Trump’s company—then called Trump Hotels & Casino Resorts—how to make it appear legal by linking it after-the-fact to a charitable effort.

The Newsweek investigation—its latest into Trump’s sprawling business empire—is based on interviews with former Trump executives, internal company records, and court filings. According to legal experts who spoke with the magazine, Seven Arrows’ role as a middleman between Trump and Cuba would not have mitigated Trump’s corporate liability if the feds had discovered his company had reimbursed the consulting firm for the money it had spent in Cuba without U.S. approval. The statute of limitations for such a violation, however, ran out long ago.

Still, the timing of both Trump’s previously unknown foray into Cuba and the revelation that it occurred are noteworthy. The secondhand Cuban expedition came roughly a year before Trump began seeking the Reform Party’s 2000 presidential nomination. As Newsweek points out, on the first day of that abbreviated campaign, Trump traveled to Miami to speak to a group of Cuban Americans and professed his support for the embargo and vowed never to spend his or his companies’ money in Cuba until the Castro regime had fallen. “As you know—and the people in this room know better than anyone—putting money and investing money in Cuba right now doesn’t go to the people of Cuba,” Trump told the crowd. “It goes to Fidel Castro. He’s a murderer. He’s a killer. He’s a bad guy in every respect, and, frankly, the embargo must stand if for no other reason than, if it does stand, he will come down.”

The report, meanwhile, comes as Trump is trying to secure the support of Florida’s Cuban American population, which constitutes a key voting bloc in a swing state that Trump almost definitely needs in order to win the White House. Trump’s problems with Hispanic voters have been well documented, but Cuban Americans—who generally back the embargo—have been the exception. Maybe not anymore.

Read more of Slate’s coverage of the 2016 campaign.