Oracle billionaire Larry Ellison once sued the city of San Jose to land his private jet at midnight—but bought his $490 million megayacht over lattes and two emails and no lawyers were involved

What would you do if you were planning to buy a superyacht? You would hire a legal team, financial advisers and go into months of negotiations and see contract reviews. But this was not the case with Oracle co-founder Larry Ellison.

When the tech billionaire commissioned what would become one of the world's most famous megayachts, he took a completely different path. Known for his competitive nature and willingness to fight lengthy legal battles, Larry Ellison finalized the deal for the 454-foot Rising Sun in one surprisingly casual meeting in London.

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The Oracle billionaire once fought the city of San Jose in federal court simply to continue landing his $38 million Gulfstream V private jet after the local airport imposed a late-night noise curfew. What is surprising is that the entire agreement with legendary yacht designer Jon Bannenberg came together over coffee, a yacht model, and just two emails, without lawyers stepping in.

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The billionaire who sued a city over a private jet made a yacht deal with two emails

Ellison's easygoing approach to buying Rising Sun became even more remarkable considering his legal history. The dispute reportedly stretched for nearly two years before Ellison secured an exemption that allowed him to continue flying into the airport at night.

A private jet's landing schedule was important enough to trigger years of courtroom arguments. Yet when it came to buying a floating palace worth nearly half a billion dollars, the agreement was sealed through two emails.

That contrast perfectly captured both Ellison's personality and the trust he placed in designer Jon Bannenberg.

Jon Bannenberg created his final masterpiece largely without modern design software

By the time Ellison approached Jon Bannenberg, several designers had already presented ideas that failed to impress the billionaire. But Jon Bannenberg's vision immediately stood apart and impressed Ellison.

According to Boat International, much of the yacht was conceived in an office that remained almost completely free of computer-aided design (CAD), reflecting the designer's traditional creative process.

Sadly, Bannenberg passed away before Rising Sun was completed. Even so, the yacht that eventually entered service remained largely faithful to his original vision, making it one of the legendary designer's final masterpieces.

One of the designer's most unusual concepts was a suspended, tube-like walkway running through the yacht's machinery spaces. Visitors would have been able to walk through and see exactly what powered the massive vessel as it cruised at speeds of around 30 knots.

Another distinctive feature involved exposed Z-frame structures separating the tender-launching areas.

Larry Ellison wanted a yacht bigger than Paul Allen's Octopus

Competition has long been part of Ellison's personality, and it even influenced the final dimensions of Rising Sun.

During development, the yacht grew significantly larger, eventually surpassing Microsoft co-founder Paul Allen's famous yacht Octopus by about 47 feet. The result was one of the largest private yachts in the world when it entered service.

Inside Rising Sun: basketball court, cinema, helipad and a private owner's deck

The sheer scale of Rising Sun allowed it to include luxury features rarely seen even on superyachts.

Among its highlights were:

• Spacious guest cabins with direct access to the exterior side decks
• A dramatic double-height cinema
• A basketball court
• A wine cellar
• A swimming pool
• A helipad
• Accommodation for 18 guests
• Space for a crew of 45
• An entire private deck reserved exclusively for Larry Ellison

The vessel measured 454 feet and displaced about 7,841 gross tons, making it one of the most impressive yachts of its era.

Why Larry Ellison sold Rising Sun after only a few years

Ellison took delivery of Rising Sun in 2004. Despite investing heavily in the project, the billionaire eventually concluded that the yacht was simply larger than he wanted.

The decision reflected a surprising shift for someone known for pursuing ever-bigger ambitions—including reportedly spending around $100 million in campaigns to win the America's Cup.

Ellison is said to have reconsidered whether such a massive yacht suited his lifestyle and even looked back fondly on his previous 244-foot yacht, Katana, which his close friend Steve Jobs had reportedly considered "just about perfect."

(With TOI inputs)