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The first signs that American policy might be shifting came in March 1998, when President Bill 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 which 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.