The Westgate Legacy: 5 Shocking Facts About David Alan Siegel’s Life, Death, And \$500 Million Empire

The recent passing of David Alan Siegel in April 2025 marked the end of an era for the timeshare industry and Central Florida business. As the founder and Executive Chairman of Westgate Resorts, Siegel built a massive hospitality empire from the ground up, becoming one of the region's largest private employers. The loss of the 89-year-old magnate has brought renewed attention to his extraordinary life, his public struggles, and the future of his vast \$500 million fortune, which is now the subject of a fresh and complex legal battle. The legacy of the self-made billionaire is not just one of business success and massive resort development; it is also a deeply personal story involving family tragedy, high-profile media exposure, and a recent, contentious family trust dispute that has emerged in the weeks following his death.

David Alan Siegel: Full Biography Profile

David Alan Siegel was a monumental figure in American business, best known for his aggressive expansion of the timeshare concept. His life was defined by entrepreneurial drive, immense wealth, and significant personal challenges, all of which were often in the public eye.

• Full Name: David Alan Siegel
• Born: May 3, 1935, in Chicago, Illinois
• Died: April 5, 2025, at the age of 89
• Occupation: Entrepreneur, Founder, and Executive Chairman of Westgate Resorts
• Primary Business: Timeshare and hospitality industry
• Estimated Net Worth at Death: Widely reported up to \$500 million (Note: Figures vary, but this is the most consistent estimate tied to the Westgate founder)
• Spouse: Jacqueline "Jackie" Siegel
• Children: 13 children
• Residence: The Versailles house in Windermere, Florida (subject of the documentary *The Queen of Versailles*)
• Key Achievements: Built Westgate Resorts into the largest privately-owned timeshare company in the world.

1. The Timeshare Empire: From Garage Startup to 22 Resorts

The foundation of David Alan Siegel's immense wealth was laid in 1982 when he founded Westgate Resorts. He started the company from his garage, opening a modest 16-unit resort in Kissimmee, Florida. This initial venture was the springboard for what would become a massive hospitality conglomerate.

Under Siegel's leadership, Westgate Resorts expanded rapidly, capitalizing on the booming vacation ownership market. The company grew to include over 13,500 rooms across 22 resorts located throughout the United States. This vast portfolio of destination resorts, which includes hotels, casinos, restaurants, water parks, and spas, established Westgate as the largest privately held timeshare company globally.

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The company became an economic powerhouse, particularly in Central Florida, where it was known as the largest private employer. Siegel’s business acumen extended beyond timeshares; he also ventured into other real estate and entertainment properties, including the purchase of the iconic Cocoa Beach Pier in 2014.

The scale of the Westgate operation—from the massive Westgate Las Vegas Resort & Casino to the flagship Westgate Lakes Resort & Spa in Orlando—demonstrates Siegel’s ambition and his ability to navigate the complex real estate and hospitality sectors for over four decades. His aggressive expansion strategy and belief in the timeshare model created thousands of jobs and cemented his status as a true industry magnate.

2. The 'Queen of Versailles' Fame and Financial Controversy

David Siegel and his wife, Jacqueline "Jackie" Siegel, were thrust into the global spotlight with the 2012 documentary *The Queen of Versailles*. The film documented their attempt to build Versailles, a 90,000-square-foot mega-mansion in Windermere, Florida, which was intended to be the largest and most expensive private home in the United States.

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The documentary captured the family's opulent lifestyle and, crucially, the dramatic financial upheaval caused by the 2008 financial crisis. The film showed the severe strain the recession placed on Westgate Resorts, forcing the company to halt construction on Versailles and struggle to maintain its existing properties. This public display of extreme wealth and subsequent financial vulnerability captivated audiences worldwide, making the Siegels household names.

Siegel initially sued the filmmakers for defamation, claiming the documentary misrepresented Westgate's financial health. Although an arbitrator later ruled in favor of the filmmakers, the film successfully portrayed the high-stakes world of the timeshare industry and the personal cost of the economic downturn on its most prominent figure. The unfinished Versailles mansion became an enduring symbol of the American housing bubble and the excesses of the pre-recession era.

3. A Personal Tragedy and Advocacy Against the Opioid Epidemic

Beyond his business ventures, one of the most defining aspects of David Siegel’s later life was a devastating personal tragedy. In 2015, his daughter, Victoria Siegel, tragically died from a drug overdose at the age of 18.

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This immense loss completely changed the focus for both David and Jackie Siegel. They transformed their grief into a powerful mission, dedicating themselves to fighting the national opioid epidemic. They established the Victoria’s Voice Foundation, an organization committed to raising awareness, providing resources, and advocating for drug prevention education among youth.

Siegel used his significant platform and resources to lobby for legislative changes and to fund initiatives aimed at saving lives. His advocacy work, often done alongside his wife, Jackie, brought a human face to the crisis and demonstrated a profound commitment to public service in the wake of his daughter’s death. This advocacy became a critical part of his public identity in his final years.

4. The Fresh Legal Battle: Trust Dispute Emerges Post-Mortem

In a development that has emerged just months after his death, the legacy of David Alan Siegel is now entangled in a complex family legal dispute. A lawsuit concerning his trust was filed in Orange County, Florida, on June 24, 2025.

The details of the lawsuit, which revolves around the administration and distribution of the timeshare magnate’s substantial estate, remain under close scrutiny. Such disputes are common among high-net-worth individuals, but the timing—so soon after his passing—highlights the immediate challenges facing the Siegel family and the future leadership of Westgate Resorts. The legal proceedings will likely determine how control and ownership of the vast Westgate portfolio are managed, potentially impacting the company's direction for years to come.

This legal battle is a critical, current update on the Siegel family's affairs, underscoring the complexities of transitioning a massive, privately-held business empire after the death of its powerful founder. The outcome of the trust dispute will be a major news story in the Central Florida business community and the timeshare industry throughout the remainder of 2025 and beyond.

5. The Westgate Legacy and Future Leadership

David Alan Siegel’s most enduring professional legacy is Westgate Resorts, which he successfully built into a multi-billion dollar entity. He was known for his hands-on approach and aggressive, decisive leadership style, which propelled the company through several economic cycles.

His passing at 89 leaves a significant void at the top of the organization. While the company has a robust corporate structure, the ultimate direction of the timeshare giant now rests on the shoulders of his successors. The family has publicly stated their commitment to "carry on his legacy," suggesting a continuation of his vision for the company's growth and expansion.

The company had recently announced an expansion plan of more than 44 new units, demonstrating that the momentum established by Siegel is expected to continue. However, the ongoing trust dispute adds a layer of uncertainty, as the legal outcome could influence the final structure of the company’s ownership and executive management. The future of Westgate Resorts will be a key indicator of the stability and long-term viability of the timeshare industry in a post-Siegel era.