Updated | A company controlled by Donald Trump, the Republican nominee for president, secretly conducted business in Communist Cuba during Fidel Castro’s presidency despite strict American trade bans that made such undertakings illegal, according to interviews with former Trump executives, internal company records and court filings.
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 Corp. 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 payment by Trump Hotels came just before the New York business mogul launched his first bid for the White House, seeking the nomination of the Reform Party. On his first day of the campaign, he traveled to Miami, where he spoke to a group of Cuban-Americans, a critical voting bloc in the swing state. Trump vowed to maintain the embargo and never spend his or his companies’ money in Cuba until Fidel Castro was removed from power.
He did not disclose that, seven months earlier, Trump Hotels already had reimbursed its consultants for the money they spent on their secret business trip to Havana.
At the time, Americans traveling to Cuba had to receive specific U.S. government permission, which was granted only for an extremely limited number of purposes, such as humanitarian efforts. Neither an American nor a company based in the United States could spend any cash in Cuba; instead, a foreign charity or similar sponsoring entity needed to pay all expenses, including travel. Without obtaining a license from the federal Office of Foreign Assets Control (OFAC) before the consultants went to Cuba, the undertaking by Trump Hotels would have been in violation of federal law, trade experts say.
Officials with the Trump campaign and the Trump Organization did not respond to emails seeking comment on the Cuba trip, further documentation about the endeavor or an interview with Trump. Richard Fields, who was then the principal in charge of Seven Arrows, did not return calls seeking comment.
Following the publication of this article on Newsweek.com, Kellyanne Conway, Trump’s campaign manager, was asked about the allegations on the television program The View. She replied that, “They paid money, as I understand, in 1998,” but went on to say that Trump had never invested in the Caribbean nation. In that statement, Conway has acknowledged that Trump broke the law. Paying the money for the business trip and meetings in Cuba – regardless of whether it resulted in an additional investment or casino deal – would directly violate the law.
A former Trump executive who spoke on condition of anonymity says the company did not obtain a government license prior to the trip. Internal documents show that executives involved in the Cuba project were still discussing the need for federal approval after the trip had taken place.
OFAC officials say there is no record that the agency granted any such license to the companies or individuals involved, although they cautioned that some documents from that time have been destroyed. Yet one OFAC official, who agreed to discuss approval procedures if granted anonymity, says the probability that the office would grant a license for work on behalf of an American casino is “essentially zero.”
‘He’s a Murderer’
Prior to the Cuban trip, several European companies reached out to Trump about potentially investing together on the island through Trump Hotels, according to the former Trump executive. At the time, a bipartisan group of senators, three former secretaries of state and other former officials were urging then-President Bill Clinton to review America’s Cuba policy, in hopes of eventually ending the decades-long embargo.
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. While in Cuba, the Trump representatives met with government officials, bankers and other business leaders to explore possible opportunities for the casino company. The former executive says Trump had participated in discussions about the Cuba trip and knew it had taken place.
The fact that Seven Arrows spent the money and then received reimbursement from Trump Hotels does not mitigate any potential corporate liability for violating the Cuban embargo. “The money that the Trump company paid to the consultant is money that a Cuban national has an interest in and was spent on an understanding it would be reimbursed,’’ says Richard Matheny, chair of Goodwin’s national security and foreign trade regulation group, based on a description of the events by Newsweek. “That would be illegal. If OFAC discovered this and found there was evidence of willful misconduct, they could have made a referral to the Department of Justice.”
Shortly after Trump Hotels reimbursed Seven Arrows, the two companies parted ways. Within months, Trump formed a presidential exploratory committee. He soon decided to seek the nomination of the Reform Party, which was founded by billionaire Ross Perot after his unsuccessful 1992 bid for the White House.
Trump launched his presidential campaign in Miami in November 1999. There, at a luncheon hosted by the Cuban American National Foundation, an organization of Cuban exiles, he proclaimed he wanted to maintain the American embargo and would not spend any money in Cuba so long as Fidel Castro remained in power. At the time, disclosing that his company had just spent money on the Cuba trip, or even acknowledging an interest in loosening the embargo, would have ruined Trump’s chances in Florida, a critical electoral state where large numbers of Cuban-Americans remain virulently opposed to the regime.
“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.”
Its Stock Price Had Collapsed
By the time Trump gave that speech, 36 years had passed since the Treasury Department in the Kennedy administration imposed the embargo. The rules prohibited any American person or company—even those with operations in other foreign countries—from engaging in financial transactions with any person or entity in Cuba. The lone exceptions: humanitarian efforts and telecommunications exports.
The impact of the embargo intensified in 1991, when the collapse of the Soviet Union ended its oil subsidies to the island and triggered a broad economic collapse. By 1993, Cuba faced extreme shortages, and Castro was forced to start printing money solely to cover government deficits. Three years later, the U.S. Congress passed the Helms-Burton Act, which codified the embargo into law and worsened Cuba’s economic decline. With many financial options closed off, Cuba attempted to find overseas investment to modernize its tourism industry and other businesses.
The first signs that American policy might be shifting came in March 1998, when President Clinton announced several major changes. Among them: resuming charter flights between the United States and Cuba for authorized Americans, streamlining procedures for exporting medical equipment and allowing Cubans in the U.S. to send small amounts of cash to their relatives on the island. However, Americans and American companies still could not legally spend their own money in Cuba.