The United States’ ambassador to Italy just made a massive personal gamble on casinos.

Billionaire diplomat Tilman Fertitta, who owns the NBA’s Houston Rockets and dozens of restaurants and hotels, has purchased at least $113 million in Caesars Entertainment since November, new federal financial documents reviewed by NOTUS indicate.

Fertitta in February also purchased between $1 million and $5 million worth of Penn National Gaming stock, according to the documents, which Fertitta signed, certified and submitted to the Office of Government Ethics between November and March.

Together, the stock purchases could be worth as much as $420 million; the exact value is unclear because executive branch officials are only required to disclose the broad ranges that their stock trades fall into.

Fertitta’s purchases coincide with reports that his holding company, Fertitta Entertainment, was attempting to buy Caesars Entertainment, which counts numerous casinos, hotels, restaurants and sportsbook operations among its holdings. Fertitta Entertainment already owns Golden Nugget Hotel and Casinos.

The gambling industry is under increasing political scrutiny, with Congress actively considering legislation that could affect sports betting, prediction markets and gambling more generally.

The State Department acknowledged questions from NOTUS but did not otherwise respond. The U.S. Embassy in Italy did not respond to requests for comment.

Steven Scheinthal, Fertitta Entertainment’s vice president, general counsel and board member, told NOTUS in an email that Fertitta “has no day-to-day control over decisions made to run his companies or assets” and that “officers overseeing both his companies and personal assets made the decision to engage in certain stock trades for business reasons, including the belief that certain equities were undervalued.”

A federal ethics agreement Fertitta signed in March 2025, ahead of his confirmation as U.S. ambassador to Italy and San Marino, didn’t expressly prohibit him from purchasing casino-related stocks. Nor did it require him to divest of most of his business interests contained within Fertitta Entertainment.

He did, however, agree to “not participate personally and substantially in any particular matter that to my knowledge has a direct and predictable effect on the financial interests of the entity or its underlying holdings.” And he resigned from certain business leadership positions and divested certain stocks, including tobacco company Philip Morris International and oil company Exxon Mobil, and cryptocurrencies, such as bitcoin and ethereum, according to his ethics agreement.

Fertitta’s large gambling industry investments do not conflict with his government work, Scheinthal said.

“None of the equities purchased of the various gaming companies have any business activities in Italy and do not constitute a conflict with Ambassador Fertitta’s duties,” Scheinthal said. “Upon his appointment, and for this very reason, he was not required to disgorge his gaming asset holdings.”

Daniel Schuman, executive director of the nonpartisan American Governance Institute, said despite Fertitta’s ethics agreement, his personal financial interests remain numerous and stand as potential distractions from his day job.

Schuman said ambassadors would ideally be “professionals, and not dilettantes.”

Morris Pearl, chairman of the board at advocacy group Patriotic Millionaires and former managing director at investment firm BlackRock, said Fertitta should regularly ask himself, “Is it ethical to be leading a business in a regulated environment when you’re representing government interests?”

In addition to Fertitta’s stock purchases, he recently used a financial technique known as opening “written call option positions” on stock he already owns in Wynn Resorts, another gambling and hotel giant, and sportsbook company DraftKings, according to his disclosures.

He disclosed the call option positions as being worth between $24 million and $117 million for Wynn Resorts and between $2 million and $10 million for DraftKings, according to his disclosures.

Forbes estimates Fertitta’s net worth is $11.2 billion. Fertitta’s personal website describes him as an “innovative visionary,” “billion dollar buyer” and “hospitality mogul” alongside his service as an ambassador representing U.S. government interests abroad.

Fertitta has long leaned into his image as a financial innovator whose hard work breeds success.“Be just like me: never, ever stop worrying about your business,” Fertitta wrote in his 2019 book, “Shut Up and Listen! Hard Business Truths That Will Help You Succeed.” “Why? Because when it comes to business and most everything else in life, there is a paddle for everybody’s ass. And you never know when it’s coming or where it’s coming from.”