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.
On February 8, 1999, Seven Arrows billed Trump Hotels & Casino Resorts, Inc. for the $68,551.88 it had incurred prior to and including a trip to Cuba on behalf of Trump Hotels & Casino Resorts Inc.
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.”
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.
Donald Trump at a taping of “Larry King Live” on CNN in New York City on October 14, 1999. Trump said he was moving toward a possible bid for the United States presidency with the formation of a presidential exploratory committee. Reuters
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.
Fidel Castro speaks with his brother Raul Castro, right, during the morning session of the Cuban National Assembly on December 21, 1998. Reuters
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.
That fall, as critics pressured Clinton to further loosen the embargo, Trump Hotels saw an opportunity. Like the Communist regime, the company was struggling, having piled up losses for years. In 1998 alone, Trump Hotels lost $39.7 million, according to the company’s financial filings with the Securities and Exchange Commission. Its stock price had collapsed, falling almost 80 percent from a high that year of $12 a share to a low of just $2.75. (After multiple bankruptcies, Trump severed his ties with the company; it is now called Trump Entertainment Resorts and is a subsidiary of Icahn Enterprises, run by renowned financier Carl Icahn.)
The company was desperate to find partners for new business that offered the chance to increase profits, according to another former Trump executive who spoke on condition of anonymity. The hotel and casino company assigned Seven Arrows, which had been working with Trump for several years, to develop such opportunities, including the one in Cuba.
On February 8, 1999, months after the consultants traveled to the island, Seven Arrows submitted a bill to Trump Hotels for the $68,551.88 it had “incurred prior to and including a trip to Cuba on behalf of Trump Hotels & Casino Resorts Inc.”
The 1999 document also makes clear that executives were still discussing the legal requirements for such a trip after the consultants had already returned from Cuba. The government does not provide after-the-fact licenses.
“Under current law trips of the sort Mr. Fields took to Cuba must be sanctioned not only by the White House but are technically on behalf of a charity,’’ the bill submitted to Trump Hotels says. “The one most commonly used is Carinas Cuba.”
The instructions contain two errors. First, while OFAC is part of the executive branch, the White House itself does not provide licenses for business dealings in Cuba. Second, the correct name of the charity is Caritas Cuba, a group formed in 1991 by the Catholic Church, which provides services for the elderly, children and other vulnerable populations in the Caribbean nation. Caritas Cuba did not respond to emails about contacts it may have had with Trump Hotels, Seven Arrows or any individuals associated with them.
The invoice from Seven Arrows was submitted to John Burke, who was then the corporate treasurer of Trump Hotels. In a lawsuit on a different legal issue, Burke testified that Trump Hotels paid the bill in full, although he denied recognizing the document.
Donald Trump at a taping of “Larry King Live” on CNN in New York City on October 14, 1999. Reuters
The Cuba venture was one of two assignments given to Seven Arrows at that time, and the second has already emerged as an issue in the GOP nominee’s bid for the presidency. Trump Hotels also paid the consulting firm to help develop a deal with the Seminole tribe of Florida to partner in a casino there. Knowing that the Florida Legislature and governor opposed casino gambling in the state, Trump authorized developing a strategy to win over politicians to get the laws changed in an effort named the “Gambling Project.” The law firm of Greenberg Traurig was retained to assemble the strategy. A copy of the plan prepared by the lawyers showed the strategy involved hiring multiple consultants, lobbyists and media relations firms to persuade the governor and the Legislature to allow casino gambling in the state. The key to possible success? Campaign contributions.
The plan states “the executive and legislative branches of Florida government are driven by many influences, the most meaningful of which lies in campaign giving.” For the Legislature, it recommends giving to “leadership accounts” maintained by state political parties, rather than to individual lawmakers, because “this is where the big bucks go and the real influence is negotiated.” Records show Seven Arrows also incurred $38,996.32 on its work on the project, far less than it spent for the Cuba endeavor.
Aside from deceiving Cuban-Americans, records of the 1998 initiatives show that Trump lied to voters about his efforts in Florida during that period. At the second Republican presidential debate in September 2015, one of Trump’s rivals, Jeb Bush, said the billionaire had tried to buy him off with favors and contributions when he was Florida’s governor in an effort to legalize casino gambling in the state. “Totally false,’’ Trump responded. “I would have gotten it.”
The documents obtained by Newsweek give no indication why the $39,000 spent on Seven Arrows’ primary assignment—arranging for a casino deal with the Seminole tribe—was so much less than the $68,000 expended on the Cuba effort. The former Trump executive could not offer any explanation for the disparity.
Though it has long been illegal for corporations to spend money in Cuba without proper authorization, there is no chance that Trump, the company or any of its executives will be prosecuted for wrongdoing. The statute of limitations ran out long ago, and legal analysts say OFAC’s enforcement division is understaffed, so the chances for an investigation were slim even at the time.
And perhaps that was the calculation behind the company’s decision to flout the law: the low risk of getting caught versus the high reward of lining up Cuban allies if the U.S. loosened or dropped the embargo. The only catch: What would happen if Trump’s Cuban-American supporters ever found out?