In recent weeks, while President Trump was locked in an unusually testy standoff with Prime Minister Giorgia Meloni of Italy, the United States ambassador to Rome was on a monthslong tour of Italy’s coastline aboard his $450 million superyacht.
As the leaders’ spat escalated over the Independence Day weekend, the ambassador, Tilman J. Fertitta, moored the 384-foot, seven-deck yacht off Palermo in Sicily to host a phalanx of Sicilian dignitaries.
The visitors could gawk at the boat’s pools, hot tubs, spa that offers facials and pedicures, movie screening room, putting green, multiple bars and two helicopters. They sipped wine, nibbled antipasti and posed for the ambassador’s Instagram feed — shoeless, as footwear is forbidden on the yacht — in rooms decorated with fluorescent artwork, varnished wood, crystal sculptures and chandeliers.
Mr. Trump was about to roast Ms. Meloni, posting on social media that he needed to take out a “restraining order” against her, two weeks after he claimed she had “begged” him for a photo at a gathering of world leaders. Mr. Fertitta, 69, seemed unconcerned by the political fracas, telling me that weekend on the yacht that he had talked to Mr. Trump and Ms. Meloni “in the last couple of weeks.”
“I listened to ’em both,” he said, speaking in his heavy Texas twang. “And they both make sense to me.”
The president is “upset with Giorgia Meloni,” Mr. Fertitta conceded in the 90-minute interview as he spread his arms across the back of a large couch and rested his white-socked feet on a coffee table. “And so he lets the world know it.”
“It doesn’t affect my relationship or the American-Italian relationship,” he added.
There are those who feel Mr. Fertitta is not practicing much diplomacy during the worst public feud between American and Italian leaders in living memory. Mr. Trump is furious at Italy’s decision not to support the war in Iran, and Ms. Meloni has lashed out at Mr. Trump, saying he picked a fight with the pope.
“It sounds like something that comes from a movie, from an Italian comedy, like the guy who wants to cruise around the coast,” said Michele Masneri, a novelist and columnist at Il Foglio, an independent newspaper. “The job of an American ambassador, I’d say, is like 60 percent being a high-scale tourist,” Mr. Masneri added.
His sailing has also attracted criticism for its cost to the Italian state. An opposition lawmaker has called for a government inquiry into how much Italy is spending on providing a police escort to secure the yacht. The Italian government declined to comment.
Mr. Fertitta, the owner of a restaurant and casino empire as well as the Houston Rockets basketball team, says it is all worth it.
“How many people ever get to come on a boat like this?” Mr. Fertitta said of Boardwalk, the sixth yacht that he has given that name. “People love successful people. Everybody wants to be successful. And anybody who says they don’t is just lying to you.”
The way Mr. Fertitta sees it, giving Italians a glimpse of how the 0.1 percent live helps to make the kind of people-to-people connections that ambassadors are supposed to foster. Even if — or perhaps especially if — relations between the leaders of his home country and his host nation have deteriorated.
By and large, though, the guests he hosts aboard the yacht come from a narrow band of Italian society. The mayor of Naples, Gaetano Manfredi, attended a reception on the yacht last month. “The people I met on the ship,” he said, “were the people who represent the city’s ruling class.”
Mariangela Zappia, Italy’s former ambassador to the United States, said she saw value in Mr. Fertitta’s approach because the yacht tour relegated the personal agita between the two leaders to “the background.” Mr. Fertitta, she said, can “demonstrate village by village, port by port, that this relationship is in fact very lively and thriving.”
Mr. Fertitta was not specific about how often he spoke to Italian officials, but Antonio Tajani, Italy’s foreign minister, said in a statement that the ambassador had helped “when we need to understand something.”
A Bipartisan Political Donor
Even among politically appointed ambassadors, who are often selected in part as a reward for campaign donations, Mr. Fertitta stands out.
Based on Forbes’s billionaire rankings, which estimate his worth at $11.1 billion, he is by far the richest envoy appointed by the Trump administration. When he first arrived in Rome last summer, Mr. Fertitta said, he spent about $3 million of his own money renovating the private living spaces at Villa Taverna, the official residence of the U.S. ambassador.
Although he identifies as conservative, he is a political chameleon who has donated to both major parties, sometimes during the same electoral cycle. Recently, he has generally given more to Republicans, but he hosted fund-raisers at his Houston home in the 1990s for President Bill Clinton and calls the Democratic senator Mark Kelly a friend. During the 2024 race, he donated $13,200 to Kamala Harris’s campaign and gave roughly $500,000 to Mr. Trump’s political action committees, according to public filings.
He explained that rather than hewing to strict partisan affiliations, he is “a loyal American.”
In a nod to the flexibility of his politics, Mr. Fertitta said that Italian officials were “smart enough to know” that they would not necessarily have to deal with Mr. Trump forever. “Just because one president and one administration wants to do things one way, that doesn’t mean that two and a half years from now another president isn’t going to do things different,” he said.
Indeed, Mr. Fertitta first started to muse about the ambassadorship to Italy while raising money for Mr. Clinton, he said.
At the time, though, Mr. Fertitta was too busy trying to expand his business, he said. Several of his associates in Houston said that even this time around, they did not expect him to actually want the job.
John Whitmire, the Democratic mayor of Houston, called Mr. Fertitta “as big a name as we’ve got in Houston in terms of networking” and said he was surprised Mr. Fertitta wanted to leave his business empire for the job in Rome. Now, though, “I think he’s enjoying the importance of the job of the ambassador,” Mr. Whitmire said.
Mr. Fertitta’s great-grandparents emigrated from Sicily more than 130 years ago, and he has for years tried to maintain a relationship with the country. In 2021, he tried to buy A.C. Milan, an Italian soccer team once owned by Silvio Berlusconi, the former prime minister who died in 2023. Mr. Fertitta’s bid was roughly $200 million short of the winning offer. “Because I was stupid,” he said.
Italy was the only country he would consider for a diplomatic posting, he said, although he does not speak the language. At an Independence Day party at the ambassador’s residence in Rome this summer, he had trouble pronouncing the names of some of the cabinet ministers whom he introduced as friends when they joined him onstage.
The Sailor-Ambassador
Mr. Fertitta’s maritime itinerary is sometimes determined as much by whim as by diplomacy, scrambling the Italian police escorts that accompany him.
While sailing around Sicily, he and his wife, Lauren Fertitta, spotted the village of Acciaroli. “I said, Look at this cute little town,” Mr. Fertitta recalled. “Let’s stop there.”
The mayor of Acciaroli, Stefano Pisani, said the consulate in Naples gave him about 15 minutes to prepare for the ambassador’s impromptu visit. Despite the short notice, the mayor was delighted to help, taking the ambassador on a three-hour tour and hosting him for a meal.
Such visits can feel like the arrival of a small expeditionary force.
On July 4, with more notice, Boardwalk anchored outside the storied port of Cefalù, Sicily. Mr. Fertitta’s entourage motored in on two skiffs, including his wife, his youngest daughter, two of his adult sons and a group of friends, Italian security agents and yacht staff members.
Curious bystanders, standing knee-deep in the water to snap photos, did not seem to know who Mr. Fertitta was, although one man raised his fist in the air and said, “Viva Trump!”
Dressed in a linen shirt and formal sneakers, Mr. Fertitta joined the Cefalù mayor for a walk through the city, where his great-grandfather lived before setting sail in 1887 for the United States.
At City Hall, Mr. Fertitta presented Italian editions of his book, “Shut Up and Listen!,” to the mayor, met with more than 15 distant relatives, posed for photos and hailed “truly one of the most special days I’ve ever had.” Giuseppe Marciante, the bishop of Cefalù, showed Mr. Fertitta marriage registries that traced his family ties to the city to the 16th century.
Later, the ambassador presented the bishop with an engraved silver dish. “This has my name on it,” he said. “I don’t want you to forget me.”
Back on the yacht, I asked him if he was having fun in his job.
He looked puzzled. “I don’t really look at anything as fun,” he said. Still, he added, “It’s a very enjoyable job.”
In fact, he said, he would consider returning to Italy as ambassador for a second term, even under a different administration.
“It wouldn’t matter to me who the president was,” he said.
Still, he said, he had “no desire” to run for elected office himself. “Because there’s no job that I could hold and I could be on this boat,” he said.
Josephine de La Bruyère contributed reporting from Rome.
