Tiffany Trump’s Family Cruised the Mediterranean on an Oil Mogul's Yacht

Massad Boulos traveled to Libya in July as the State Department’s senior Africa adviser. But as he talked to energy executives and government leaders, his other position was no less important. He was also the father-in-law of President Trump’s daughter Tiffany.

That family connection was so significant that some Libyan officials had privately taken to calling him “Abu Tiffany,” Arabic for “Tiffany’s father.”

While Mr. Boulos posed for photographs and announced deals to ramp up Libyan oil and gas production, Tiffany Trump and her husband, Michael Boulos, were cruising the French Riviera aboard one of the world’s largest superyachts — owned by a major broker of Libyan oil.

The yacht, the Phoenix 2, is a floating palace with two helipads, a swimming pool and an 18-foot bronze figurehead of a flaming phoenix rising from its bow. It is not available to charter. But when it last was, it rented for over $1.4 million per week, with the listing highlighting an Art Deco interior and custom Steinway piano.

Massad Boulos is the face of the Trump administration’s diplomacy in Africa, a strategy that prioritizes cutting business deals over international comity and the promotion of democracy. The presence of his son and Ms. Trump on a luxury yacht owned by international billionaire executives is a measure of how hard it is to tell where the interests of government end and the Trump family begins.

Career diplomats, U.S. allies and even some members of Mr. Trump’s inner circle have become concerned as Mr. Boulos has conducted what at times has been freewheeling diplomacy in Lebanon, in the Democratic Republic of Congo and beyond.

American government officials say he has caused diplomatic dust-ups in politically delicate parts of the world. Some senior officials have cautioned him to stay in his lane and to be mindful of seeming to mix family business and diplomacy — particularly as Michael Boulos tells people that he’s pursuing business deals in Africa.

Michael Boulos and Tiffany Trump hold no public office. But weeks after they stepped off the yacht, they stepped aboard Air Force One as the president made a state visit to Britain. They were among the American dignitaries at Windsor Castle on Wednesday. Michael Boulos entered the state dinner alongside Catherine, Princess of Wales.

There is nothing necessarily illegal about a diplomat’s family (or the president’s) traveling aboard the yachts of people who stand to benefit from American foreign policy. But Mr. Trump spent years criticizing Hunter Biden, his predecessor’s son, for trying to profit off his proximity to power. Then, upon returning to office, Mr. Trump, his family and the children of some top advisers went into business with foreign governments and companies that were the subject of American diplomacy.

Massad Boulos declined to answer questions about the yacht trip. So did a spokesman for Michael Boulos and Tiffany Trump, who called it a “personal and private vacation.”

A spokeswoman for BGN said that Ms. Bayegan was not on the Phoenix 2 at the time, leaving it unclear who had invited the Boulos-Trump family. “Inquiries about individuals who may have been on board the yacht Phoenix 2 are not relevant to BGN’s business operations in Libya,” the spokeswoman, Sharon McKoy, said.

The State Department would not comment on whether senior officials were aware of the trip but sent a series of statements from American diplomats praising Massad Boulos for his efforts in Africa. Mr. Boulos would not discuss the Mediterranean vacation; he defended his record and said he was working toward peace and prosperity in Africa.

Trump administration officials have publicly praised Mr. Boulos, a diplomatic neophyte who until this year ran a family-owned Nigerian trucking company. Secretary of State Marco Rubio called him a “superstar” for helping broker a peace accord between Rwanda and the Democratic Republic of Congo.

Mr. Boulos has a unique position in the Trump administration. His immediate boss is unclear, he holds jobs in both the State Department and the White House, he required no Senate confirmation, and he has no duty to publicly disclose his business interests.

White House and State Department officials who would normally try to rein in Mr. Boulos say they are in a tough spot. Officials said they had treaded cautiously for fear of crossing a man who now counts himself as part of the president’s family.

Mr. Boulos denied that there had been disputes over his diplomacy. He said that the United States spoke with one voice and that his outreach to foreign officials had been “productive, successful and welcomed with genuine appreciation.”

His diplomatic tenure got off to a rocky start.

Concerns about Mr. Boulos began in his first months in government. As the president’s Middle East adviser, he took meetings and calls with Lebanese officials outside the normal diplomatic channels and pushed his preferred candidates for positions atop the Lebanese central bank and finance ministry.

State Department diplomats responded by taking the awkward step of asking Lebanese officials to run their diplomacy through the American Embassy, not through Mr. Boulos, according to two senior officials.

This summer, White House officials started getting calls from Morocco: Mr. Boulos was seeking an audience with the king. American officials, unclear as to Mr. Boulos’s agenda and unaware of a need for the monarch’s time, privately told the Moroccans to decline the request.

That followed a misstep, widely reported in the region, in which Mr. Boulos inadvertently suggested that Mr. Trump’s carefully negotiated deal that persuaded Morocco to normalize relations with Israel was suddenly open for renegotiation.

He said that his comments on Morocco had been taken out of context and that he had not personally or improperly sought a meeting with the king. “I have and will continue to engage officials at the most senior levels,” he said.

Mr. Boulos’s turn as a diplomat is the latest twist for a man whose titles have not always matched his résumé.

For years, he was referred to as a billionaire despite there being no evidence that he was one. State Department officials call him “Dr. Boulos,” but he has neither a medical degree nor a Ph.D. (He has a law degree, but, even in his home of Nigeria, lawyers are typically not called “doctor.”)

After a few months as Mr. Trump’s Middle East adviser, he became the State Department’s senior adviser to Africa. He publicly identifies as serving in both jobs.

Mr. Boulos’s most celebrated diplomatic accomplishment is the Rwanda-Congo agreement.

Rwanda-backed troops occupied Congolese territory, giving them control of lucrative mines. Thousands of people were killed and hundreds of thousands more were displaced.

According to Mr. Trump, Mr. Boulos was central to a deal to end the war.

One key to the peace was an agreement over mining in the region of Congo known as Rubaya. The deal called for an American company to formalize and industrialize mining operations, allowing Rwanda and Congo to share wealth rather than fight over it. The United States would win by blunting Chinese access to rare-earth minerals.

Despite a Washington treaty ceremony, the mining deal remains unsettled. Fighting has continued between Congolese and Rwanda-backed forces.

Mr. Boulos is at the heart of delay, according to two Trump administration officials and a mining industry consultant, all of whom had spoken directly to the Congolese government about the issue. They said that Mr. Boulos had urged the Congolese not to finalize the agreement with Mr. Beach because Mr. Boulos was making other arrangements.

Congo’s mining director said that he would not discuss conversations with the American government.

Mr. Boulos did not deny blocking the deal but said negotiations continued. “The Rubaya mining area is one of dozens of mining assets that are being discussed,” he said. He said the Congolese would ultimately sign a deal at the White House.

In Libya, Mr. Boulos’s diplomacy has puzzled U.S. allies.

The Boulos-Trump family’s time aboard the Phoenix 2 is likely to reinforce the growing perception among officials and business leaders in Libya that Mr. Boulos, as a diplomat, is picking sides in the country’s fractious politics.

Libya is divided, with a military general running a government in the east, and an interim government in the west. The interim government, led by the Dbeibeh family, has remained in power long past its mandate and has resisted international calls for elections.

That makes Libya combustible. It regularly erupts into militia-fueled violence.

From their first meeting with Mr. Boulos, Libyan officials on both sides of the divide said that they were bewildered by his lack of knowledge. “He couldn’t differentiate between west and east,” one official said.

This spring, Mr. Boulos met in Qatar with Libya’s national security adviser, Ibrahim Dbeibeh. Mr. Dbeibeh, nephew of the prime minister, floated an extraordinary proposal: If the United States were to unfreeze some of the $70 billion that has been under sanctions and locked in Western banks since before the fall of Col. Muammar el-Qaddafi’s dictatorship, Libya would commit that money to American companies through construction contracts.

Merely considering such an arrangement could be seen as American support for the Dbeibeh government.

Then, on the night of July 23, Mr. Boulos arrived in Libya’s capital, Tripoli. After announcing oil deals and promising more, Mr. Boulos headed for a seaside villa to dine with Ibrahim Dbeibeh. Unlike other meetings with officials in the east and west, this one was not publicized.

All of this could merely reflect Mr. Trump’s diplomatic style, which unabashedly prioritizes business deals for American companies, even with strongmen and autocrats.

If so, Mr. Boulos has offered conflicting accounts on the matter.

At first, Mr. Boulos denied dining at Mr. Dbeibeh’s villa. Confronted with more information about the dinner, he acknowledged dining there.

“Diplomatic engagements, both public and private in nature, take place in a variety of settings,” he said. He said it was a working dinner and that State Department diplomats had joined him at the villa, which he characterized as “a government-owned location.”

Mr. Boulos similarly categorically denied discussing frozen assets. After multiple high-ranking Libyan officials and a U.S. official confirmed that Mr. Dbeibeh had, in fact, floated the cash-for-contracts idea, Mr. Boulos added: “Whatever perception some Libyans may hope to create, this issue is a nonstarter.”

Hanging over all of this is Michael Boulos, who has expressed interest in doing business in Libya’s oil industry, according to two people, including a family associate who spoke directly about it with him. Michael Boulos’s interest is also well known in Tripoli’s business community, said Basit Igtet, a prominent Libyan businessman. (A family spokesman said that Michael Boulos had no interest in pursuing business in Libya or in the oil and gas industry).

Any such business would effectively require the support of the Dbeibeh government.

“Libya deserves better than a broker like Boulos,” Mr. Igtet said, referring to Massad. “The situation is just too sensitive.”

This summer, concern spread among a small group of Trump advisers in Washington who had heard that the Boulos-Trump family was aboard a Turkish billionaire’s yacht.

Then, Tiffany Trump and her family posted photographs and videos that showed more than a week of hopping between the Phoenix 2 and another yacht, the Magna Grecia. Records show it is owned by a sprawling conglomerate controlled by the Greek billionaire Ioannis Papalekas. His company also has interests in the energy sector.

One person involved in the Phoenix 2’s operations, speaking on condition of anonymity, said that the Boulos-Trump family did not pay the Bayegans for their time on the yacht. Owners of yachts this size often allow access to friends, associates and their guests.

Exactly when they boarded the Phoenix 2 and whether they spent the night is unclear. But digital evidence from ship-tracking websites and the Trump family’s social media posts indicate they spent time on board during the period of July 17 to July 27.

The Magna Grecia’s owner, Mr. Papalekas, also has a controlling interest in a company that runs a private estate on the island of St. Marguerite. The estate, known as Le Grand Jardin, was once home to Louis XIV and rents for up to $290,000 per week. Photographs show that Ms. Trump and her mother, Marla Maples, spent time there while on their yacht trip.

Mr. Papalekas could not be reached. His company’s Cypriot lawyers took questions but did not respond.

On July 24, one day after Massad Boulos met with Libyan officials to discuss increasing oil output, Ms. Trump took a picture of her husband on the deck of the Phoenix 2, docked at the exclusive Monaco Yacht Club.

Riley Mellen, Julie Tate and Maggie Haberman contributed reporting.