David A. Siegel: The Man Behind The Mansion And The Empire

What’s Up with David A. Siegel’s Net Worth?

Let’s talk about David A. Siegel, a guy who knows how to build an empire—and a mansion or two. This American entrepreneur has racked up a net worth of $500 million, and it’s all thanks to his brainchild, Westgate Resorts. This Florida-based timeshare company isn’t just his day job—it’s his passion. David serves as its president and CEO, and if that wasn’t enough, he’s also been featured in the award-winning documentary "The Queen of Versailles." That film dives deep into his financial struggles after the 2008 real estate collapse, while he and his wife Jackie were trying to build one of the most extravagant homes in U.S. history. Stick around, and we’ll break it all down for you.

David’s Early Days

David A. Siegel was born in Chicago, Illinois, on May 3, 1935. His parents, Sadelle and Sid Siegel, owned a grocery business, which they moved to Miami when David was just ten. Growing up in Miami, he attended Miami Senior High School and later enrolled at the University of Miami to study management and marketing. But let’s be honest, David wasn’t one for the traditional path. He left college without graduating, proving that sometimes the best entrepreneurs are the ones who march to their own drum.

Building the Empire: David’s Career

David didn’t just sit around waiting for opportunities to come to him. No, he went out and created them. He co-founded Mystery Fun House, an Orlando attraction that opened in 1976 and operated until 2001. But that’s not all—he also produced the movie "Night Terror" in 2002. Now, here’s where things get really interesting: Westgate Resorts. This timeshare company, which David founded, became his life’s work. He’s still at the helm as President and CEO, but his business ventures don’t stop there.

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David also runs Central Florida Investments, Inc., and Central Florida Investments Resorts Management, Inc., where he oversees travel services, transportation, retail, telecommunications, and construction. In the golden years of 2004 to 2007, David’s paper net worth hit a billion-dollar mark. But then, the 2008 financial crisis hit, and everything changed. Despite the challenges, David kept pushing forward. In 2012, he made headlines by sending an email to his employees threatening to fire them if President Obama was re-elected. Spoiler alert: he didn’t follow through. And in 2015, he appeared on ABC’s "Celebrity Wife Swap," where he swapped lives with actor Jeremy London.

"The Queen of Versailles": A Look Inside the Documentary

David and Jackie Siegel are the stars of Lauren Greenfield’s award-winning documentary, "The Queen of Versailles." The film takes us inside their lives as they attempt to build their opulent mansion, modeled after the Palace of Versailles. But it’s not all glitz and glamour. The documentary captures the economic downturn that hit the U.S. in 2008 and the challenges the Siegels faced as they struggled to sell off expensive assets to keep their business afloat. David’s attempts to hold onto Westgate’s Las Vegas high-rise resort, the PH Towers Westgate, didn’t go as planned. The Siegels even filed two lawsuits against the filmmakers but lost both. It’s a story of ambition, setbacks, and resilience.

The Versailles Mansion: A Monument to Dreams

David and Jackie’s Versailles mansion in Windermere, Florida, is the stuff of legends—or maybe nightmares, depending on your perspective. Construction began in 2004, just as David’s timeshare business was booming, and his net worth was nearing billionaire status. The goal? To build the largest single-family home in America. The result? A 90,000-square-foot estate complete with 14 bedrooms, 32 bathrooms, 11 kitchens, a roller rink, an ice skating rink, a bowling alley, a 30-car garage, three levels, three indoor pools, two outdoor pools, two tennis courts, a baseball diamond, a fitness center with a 10,000-square-foot spa, and a two-story movie theater. But just as the dream seemed within reach, the 2008 financial crisis hit, leaving the mansion incomplete. The Siegels’ struggles were immortalized in "The Queen of Versailles." Eventually, their finances improved, and construction resumed, with Jackie taking the reins. This mansion has been under construction for over 20 years, and it’s still a work in progress.

The NYC Penthouse: A New Chapter

In 2023, Jackie and David purchased a duplex in NYC’s Tribeca neighborhood for $8.7 million. By January 2024, they were ready to move on and listed the unit for sale at $19.5 million. It’s a bold move, but hey, when you’ve built a mansion modeled after the Palace of Versailles, a NYC penthouse is just another chapter in the story.

David’s Personal Life: A Family Man

David’s personal life is as fascinating as his business ventures. He has nine biological children and two adopted ones. His first marriage to Geraldine Florence Sanstrom lasted from 1961 to 1969, and he was married to Bettie Tucker from 1970 to 1997. David remained the custodial parent for all his children. In 1998, he met his third wife, Jackie Siegel, and they tied the knot in a Jewish ceremony in 2000. Tragedy struck in 2015 when their 18-year-old daughter, Victoria Siegel, passed away from a drug overdose. This personal loss motivated David to become a vocal advocate against drug abuse. In 2008, David faced a sexual harassment lawsuit brought by a former Westgate employee, Dawn Myers. After a trial, the jury awarded her $5.4 million, but a judge later reduced the award to $610,000. Myers received $103,622 in compensatory damages and $506,847 in punitive damages.