When you hear the name David Siegel, your mind probably jumps straight to that massive, unfinished limestone monster in Orlando. Or maybe you think of the "Queen of Versailles" documentary where his wife, Jackie, tries to navigate a Walmart like it’s a foreign country. It’s easy to get caught up in the reality TV of it all. But honestly? The real story behind the net worth of David Siegel is way more complicated than a half-built mansion. It's a story of a guy who basically invented the modern timeshare industry, lost a massive chunk of his soul to the 2008 crash, and then, against all odds, clawed his way back to the top of the heap.
There's actually a lot of confusion out there because there are two very famous David Siegels in the high-stakes world of money. One is the computer scientist who co-founded the hedge fund Two Sigma. He’s worth billions—roughly $6.2 billion to $8 billion depending on which day you check the Bloomberg Billionaires Index. But the David Siegel most people are googling—the Westgate Resorts mogul—lived a very different, very public life until his passing in April 2025.
The Timeshare King and the $500 Million Gamble
David Alan Siegel didn't just stumble into money. He started Central Florida Investments (CFI) back in 1970. He was a real estate guy through and through. In 1982, he took a tiny 16-unit resort and turned it into Westgate Vacation Villas. That was the spark. Before he knew it, he was sitting on the largest privately-owned timeshare company in the world.
Think about that for a second.
Private. No shareholders to answer to. No quarterly earnings calls to sweat. Just David. At his peak before the Great Recession, his net worth was comfortably in the billionaire category, often cited around $1 billion or more. But then 2008 happened. Banks stopped lending. The "cheap money" that fueled timeshare sales evaporated. He almost lost everything, including his crown jewel: the PH Towers in Las Vegas.
He didn't quit, though. While the documentary made it look like the end of an era, Siegel spent the next decade restructuring. By 2024, right before he stepped down as CEO to hand the reins to Jim Gissy, estimates of his net worth had rebounded significantly. Some industry insiders and Florida business journals pegged the value of his empire at $7 billion. That number includes the Cocoa Beach Pier, the Westgate Las Vegas Resort & Casino, and over 15,000 hotel rooms across the country.
Why the Estimates for David Siegel Net Worth Vary So Much
You'll see numbers all over the place. $500 million. $2 billion. $7 billion. Why the massive gap?
- Private Equity vs. Liquidity: Because Westgate is privately held, we don't have a stock price to look at. We have to guess based on revenue and assets.
- Real Estate Valuations: A 90,000-square-foot house (Versailles) is worth a lot on paper, but only if someone actually wants to buy a house with a bowling alley and a 20-car garage.
- The "Two Sigma" Confusion: As mentioned, the other David Siegel—the quant hedge fund genius—is worth about $7 billion. Frequently, Google's algorithms accidentally mash their data together. If you see a "David Siegel" on a Forbes 400 list, it's almost always the Two Sigma co-founder, not the Westgate guy.
The Westgate Siegel was less about liquid cash and more about massive, tangible land holdings. His wealth was tied up in the dirt and the buildings. When the travel industry booms, he's a multi-billionaire. When a pandemic or a recession hits, his "paper wealth" takes a nosedive.
The Versailles Effect: Is the Mansion an Asset or a Liability?
The Versailles house in Windermere, Florida, is basically a mascot for the net worth of David Siegel. It's modeled after the Palace of Versailles in France. It has 14 bedrooms, three indoor pools, and a ballroom.
Is it worth $100 million? Maybe. But for David, it was more of a symbol. It represented the fact that he survived the 2008 crash. Construction famously stalled for years during the downturn, and the house sat as a skeletal reminder of "hubris." But he eventually got it back under construction. Finishing that house was a personal statement that his net worth was back where it belonged.
More Than Just Vacations: The Business Diversification
Siegel wasn't just a one-trick pony. His CFI family of businesses touched a little bit of everything in Central Florida:
- Retail and Insurance: He owned travel services and insurance firms that supported the timeshare business.
- Sports: He once owned the Orlando Predators arena football team.
- Media: He even dabbled in film production.
- Philanthropy: Following the tragic loss of his daughter Victoria in 2015, he shifted a huge portion of his focus (and money) to Victoria’s Voice Foundation.
It's sort of wild to think about. He was a guy who dropped out of the University of Miami and ended up controlling a huge chunk of the Florida skyline.
What Actually Happened to His Wealth in 2025?
Upon his death in April 2025, the question of his estate became a major topic in business circles. With 12 children and a high-profile wife, the distribution of his assets is complex. However, the company remains a juggernaut. Just months before he passed, Westgate acquired VI Resorts, adding 40 more locations to the pile. This move alone suggests the company’s valuation was at an all-time high.
The net worth of David Siegel at the time of his passing was likely in the $3 billion to $5 billion range when accounting for debt and the private nature of his holdings. While the $7 billion figure is often cited, that's usually the "enterprise value" of the company rather than the cash in his personal bank account.
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Actionable Insights for Understanding High-Net-Worth Portfolios
If you're looking at Siegel's life as a case study for wealth building, there are a few real-world takeaways you can actually use.
Don't ignore the power of private ownership.
Siegel's ability to keep his company private meant he could weather the 2008 storm without being forced into a fire sale by a board of directors. If he had been public, Westgate likely wouldn't exist today.
Real estate is a hedge, but it's not liquid.
You can be "worth" a billion dollars and still struggle to pay the electric bill if your money is all tied up in half-finished mansions and resort towers. Diversifying into liquid assets is what separates the "rich on paper" from the truly stable.
Brand yourself.
Love him or hate him, David Siegel was the face of his brand. That visibility—enhanced by the documentary—gave him a level of fame that translated into business leverage. People knew Westgate because they knew David and Jackie.
To get a true sense of where his estate stands now, you'd have to look at the 2026 filings for the Westgate Foundation and the probate records in Orange County, Florida. It's a massive web of trusts and corporations that will take years to fully untangle.