A new deep dive from The New York Times reveals how Michael Boulos, the 27-year-old businessman who married President Donald Trump's youngest daughter, Tiffany, in 2022, has financially benefited from a series of strange deals made with his in-laws.

The deals started "almost immediately" after the couple became engaged, reported Justin Scheck, Tariq Panja, Jo Becker, and Bradley Hope.

"Mr. Boulos, working for his cousin’s international yacht brokerage, sold his future brother-in-law Jared Kushner on an investment in a roughly 50-meter superyacht," noted the report. However, without Kushner's knowledge, "the firm overcharged him and worked to conceal the true price from him, contemporaneous text messages show. The exact amount is unclear but the messages and a lawyer’s written description of the deal say the overcharge was $2.5 million."

Shortly after that, Boulos' cousin Jimmy Frangi "promised to get a Saudi businessman invited to the Boulos-Trump wedding so that the businessman could pose for photographs with the Trumps and project a closeness with the family," writing to the businessman, “We want you to be at the top of the guest list.”

Ultimately, neither deal was much of a success, with the yacht sitting half-built in Greece and the businessman not invited to the Florida wedding — but all of this was just the beginning, as Boulos and his father, Massad, have tried to leverage their closeness to the Trump family to gain not just business deals but power and influence within the government, echoing the way Trump's own family has spent years profiting off of Trump's official duties.

"Mr. Trump’s election in 2024 propelled Massad Boulos into government. He became a presidential adviser on the Middle East and then a senior State Department adviser on Africa," said the report. "And Michael Boulos is seeking business there, according to the former prime minister of Guinea." That former prime minister, Lansana Kouyaté, confirmed Boulos is trying to “put together some investors from the United States and some governments in Africa,” but wouldn't discuss specifics.

This comes after recent reporting that indicates the elder Boulos has been frustrated by the limited powers he has been given by the Trump administration in his capacity as an adviser.