From Yachts to AI Empires: Larry Ellison’s Evolution from Playboy Billionaire to Tech Power Broker

Edited by: TJVNews.com

For decades, Larry Ellison was the larger-than-life Silicon Valley icon who seemed to revel in defying expectations — not as much through the innovations of his company, Oracle, but through a lavish lifestyle few tech executives dared emulate. From constructing a $200 million Japanese-style imperial villa in California to purchasing the sixth-largest Hawaiian island, Ellison appeared more captivated by opulence and adventure than by the inner workings of his multibillion-dollar database empire.

But as The New York Times reported on Tuesday, in a sweeping profile of the Oracle founder, the 80-year-old billionaire is undergoing a transformation — from exuberant billionaire playboy to strategic empire-builder with ambitions that increasingly mirror those of his close ally, Elon Musk. What was once a life defined by yachts, luxury real estate, and splashy romances is now increasingly consumed by cloud infrastructure, artificial intelligence, content acquisition, and political proximity.

Larry Ellison’s past is a study in decadence and defiance. Known for his penchant for racing yachts — including skipping Oracle’s 2013 annual conference to pursue (and win) the America’s Cup — Ellison cultivated an image that seemed to say: I have more money than anyone, and I’ll enjoy it however I like.

Books were written about his ego, with one famously titled “The Difference Between God and Larry Ellison: God Doesn’t Think He’s Larry Ellison.”  As The New York Times report recounted, Ellison’s commitment to spectacle often outshone the public understanding of what Oracle actually did — and, at times, his own engagement with it.

Now, with a personal fortune of around $175 billion, Ellison seems less interested in flaunting his wealth than using it to shape the future — particularly one defined by technology, media control, and artificial intelligence.

He appears increasingly aligned with Elon Musk, whom The New York Times identifies as perhaps the only tech figure closer to Donald Trump than Ellison himself. The two moguls — each with massive influence, multi-company portfolios, and a shared disdain for institutional constraints — are reshaping the interplay between private capital and public power.

In 2022, Ellison nonchalantly invested $1 billion in Musk’s Twitter acquisition, saying at the time it would be “lots of fun.” That same year, he broke Florida real estate records by purchasing a $173 million Palm Beach estate, a sum that accounted for just one-tenth of one percent of his total net worth.

But these moves, The New York Times suggests, may only be the beginning.

 

Once seen as a sleepy software giant known primarily for its database technology, Oracle is now emerging as a major player in the AI and content wars. According to the New York Times report, the company is once again in contention to acquire TikTok, the wildly popular Chinese-owned video app that the U.S. government is pressuring to divest for national security reasons.

As of this week, Oracle is rumored to be one of the leading bidders as Congress and the White House finalize demands for ByteDance, TikTok’s parent company, to sell or face a U.S. ban. The information provided in The New York Times report indicated that President Trump convened top advisers Wednesday to discuss the situation, with a Saturday deadline looming — though prior TikTok deadlines have often slipped.

Oracle nearly struck a deal in 2020 to co-own TikTok Global with Walmart, while also taking over U.S. user data storage. The cloud infrastructure portion of that arrangement materialized, but the ownership stake never did.

Now, with 1.5 billion monthly users worldwide, including 150 million in the United States, TikTok represents not just a content goldmine, but a strategic data and influence platform — and Ellison appears determined to seize it, as was noted in The New York Times report.

In parallel with Oracle’s TikTok interests, Ellison is bankrolling his son, David Ellison, in an $8 billion bid to acquire Paramount Global, the parent company of CBS, MTV, Nickelodeon, and the historic Paramount Pictures studio. This convergence is no accident. Content platforms create engagement; cloud platforms store the data; AI tools analyze it. Together, they form a loop of influence and surveillance.

As The New York Times reported, the proposed acquisition would give the Ellison family a formidable foothold in the content space — a natural complement to Oracle’s cloud infrastructure and data ambitions.

If the TikTok deal comes through, and if the Paramount purchase is approved, Ellison would be poised to control multiple major channels of content production, distribution, and data — an ecosystem not unlike Musk’s blend of SpaceX, Tesla, X (formerly Twitter), and Neuralink.

In short, Ellison is no longer content with being the guy who built Oracle and raced yachts. He now wants to become the platform through which information, entertainment, and intelligence flow — and are shaped.

Ellison’s ascent is also notable for his increasing political entanglement. As The New York Times report pointed out, he has developed a deep relationship with President Trump, and his backing of controversial ventures — from Musk’s Twitter overhaul to political donations — marks him as a billionaire comfortable in the gray zones where private influence meets public policy.

His growing portfolio now straddles entertainment, surveillance, cloud services, and national security, and it reflects a broader trend in Silicon Valley: the consolidation of corporate power around personal empires, where the boundaries between business, politics, and ideology are blurring at a rapid pace.

Richard Greenfield, a media analyst with LightShed Partners told The New York Times that, “All these pieces are coming together to form something that isn’t quite clear yet except for this: The Ellison family will be at the center.”

For decades, Ellison was the tech world’s rebel king—racing yachts instead of keynoting Oracle conferences, buying Hawaiian islands, building imperial villas, and marrying (or dating) with gusto. His office culture, by his own admission, was once defined by “management by ridicule,” and he freely acknowledged Oracle’s chaotic early years: “Oracle is run by adolescents. And that includes me.”

Yet behind the bravado was a growing ambition to influence more than just the software industry. As The New York Times report revealed, Ellison has long pursued a guiding idea he once dubbed “enlightened egotism”—making the world better, yes, but as a means of fulfilling his own desire for impact and legacy.

In January, Ellison stood onstage at the White House for the announcement of “Project Stargate,” a plan to build expansive data centers to support artificial intelligence infrastructure. The New York Times reported that President Trump, standing nearby, was asked if Elon Musk might purchase TikTok. Instead, Trump volunteered an alternative name: “I’d like Larry to buy it, too.”

Both Oracle and Ellison declined to comment on their future ambitions when reached by The New York Times. But sources suggest his agenda is becoming clearer: control over infrastructure, content, data, and influence.

Nowhere is Ellison’s evolving worldview more striking—or controversial—than in his push for what he describes as a surveillance society guided by artificial intelligence.

“Citizens will be on their best behavior, because we’re constantly recording and reporting everything that’s going on,” Ellison told Oracle investors last fall. “It’s unimpeachable.”

To many, this echoes dystopian science fiction. But Ellison presents it as a path to social harmony. He told Tony Blair at a government-reinvention symposium in Dubai that his vision includes merging thousands of databases into a single AI-analyzable repository, as was explained in The New York Times report. This system, Ellison claims, could help cure diseases, improve governance, and promote societal wellbeing.

“I think this will make for a happier citizenry,” Ellison said, appearing by video.

That vision is not without serious legal and ethical challenges. In November, Oracle reached a $115 million settlement in a California class-action suit that accused the company of improperly collecting and selling user data without consent. The report in The New York Times said that the case, while not admitting wrongdoing, reveals the growing concern about Oracle’s (and Ellison’s) hunger for information—especially as they prepare to consolidate more.

Still, for Ellison, data remains the key to unlocking his broader ambitions. As The New York Times report noted, he believes the more we know—especially if AI can make sense of it—the closer we come to resolving humanity’s deepest problems.

 

Ellison’s public persona in the 1990s and early 2000s was often caricatured: flashy, egotistical, more interested in his image than in ideology. The New York Times reported that he married romance novelist Melanie Craft in 2003 (with Steve Jobs as the wedding photographer), and told Playboy in 2002 that after three failed marriages, “There’s no question I can do it better. Can I do it worse? I don’t think so.”

In the 1990s, Ellison’s political sympathies leaned decidedly centrist-Democratic. He once joked that the Constitution should be amended to allow Bill Clinton to serve a third term. The report in The New York Times said that in those days, he praised moderates like Tony Blair, and in a 2018 statement cited Marco Rubio and Mitt Romney as examples of the kind of center-right politics he identified with.

“Bill Clinton was a centrist. Tony Blair was a centrist. Marco Rubio is a centrist. Mitt Romney is a centrist. Those are my politics,” Ellison told reporters, as quoted by The New York Times.

His political views shifted more decisively to the right in the 2000s, especially in response to what he perceived as Barack Obama’s antagonism toward Israel. This prompted a closer relationship with Israeli Prime Minister Benjamin Netanyahu and eventually opened the door to new alliances in the U.S. conservative landscape.

Ellison didn’t immediately embrace Donald Trump during the 2016 campaign. Instead, he backed Marco Rubio, then a sharp critic of Trump, in the Republican primaries. By 2020, however, the relationship had changed. Trump convinced Ellison to host a fundraiser at his Southern California golf course, The New York Times report said.  While Ellison’s name appeared as the sole host on the invitation, he conspicuously did not attend, citing illness.

But proximity soon overcame hesitation. In the lead-up to the 2024 campaign, Ellison publicly aligned himself with Senator Tim Scott of South Carolina, traveling to attend Scott’s announcement speech. Scott called Ellison “one of my mentors.” Yet when Scott’s campaign collapsed and Trump regained momentum, Ellison once again drifted toward Trump, dining with him at Mar-a-Lago, which is conveniently close to Ellison’s newly purchased Palm Beach estate, as per the information in The New York Times report.

Though Ellison has not made public donations to Trump’s campaign, he did attend a transition planning meeting at Mar-a-Lago—a signal of his deepening role in the GOP’s tech-adjacent power structure.

Ellison’s relationship with Trump isn’t just political—it has deep business implications. It was during Trump’s first term that Ellison first developed a serious interest in TikTok, the Chinese-owned video platform. As was reported in The New York Times, a 2020 proposal would have seen Oracle and Walmart acquire stakes in a new company called TikTok Global, which Trump endorsed amid rising security concerns over Chinese ownership.

That original deal fell apart, but Oracle was nonetheless entrusted with hosting U.S. TikTok user data on its cloud infrastructure—establishing a foothold that has since grown.

Now, as new pressures mount for ByteDance, TikTok’s parent company, to divest its U.S. operations, Oracle is once again a front-runner. While Walmart is no longer expected to be involved, Oracle’s CEO Safra Catz is reportedly leading negotiations. Sources cited by The New York Times indicate the deal would not grant Oracle total ownership nor access to TikTok’s algorithm—the very engine behind its viral success.

Yet for Ellison, this might be beside the point.

“Think of TikTok as video data — unstructured data that fits into another slice of that Oracle matrix,” said Terry Garnett, a former Oracle marketing chief, in remarks to The New York Times. “Whoever has the data has the power.”

Ellison’s faith in technology remains undeterred, according to friends and former colleagues. Garnett, who was once fired by Ellison but later reconciled with him, put it simply: “At the end of the day he loves technology. It’s that simple.”