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David Alan Siegel, born on May 3, 1935, in Chicago, Illinois, is an American businessman best known as the founder and CEO of Westgate Resorts, a timeshare company that has grown into one of the largest in the world. Siegel’s life story is a fascinating tale of entrepreneurship, ambition, wealth, and personal challenges. From his rise in the timeshare industry to his struggles during the 2008 financial crisis and beyond, Siegel has lived a life that captures the extremes of success and adversity.
Early Life and Education
David Siegel was born into a middle-class Jewish family and raised in Miami, Florida. His father, Sid Siegel, owned a grocery store and later a liquor business, which gave David his first exposure to running a business. His mother, Sadelle, was a homemaker.
After completing high school, Siegel attended the University of Miami, where he studied marketing and management. Though he did not complete his degree, his time at the university helped him develop the business acumen that would later drive his success. Siegel had a variety of early ventures, including owning a radio station and working in real estate, before eventually finding his niche in the timeshare industry.
The Rise of Westgate Resorts
In 1982, Siegel founded Westgate Resorts in Orlando, Florida. His company specialized in the sale of timeshares, which allow customers to buy partial ownership of a vacation property for a certain period each year. Siegel’s vision was to offer luxurious vacation experiences at affordable prices, and his business model quickly took off.
Westgate Resorts expanded rapidly during the 1990s and early 2000s, becoming one of the largest privately-owned timeshare companies in the world. Siegel’s marketing genius was evident in his aggressive sales tactics, which targeted middle-class Americans looking for affordable vacation options. By offering flexible financing and a wide range of locations, including resorts in popular destinations like Las Vegas and Orlando, Westgate Resorts became synonymous with the booming timeshare industry.
At its peak, Westgate Resorts employed thousands of people and generated billions in revenue, with over 28 resort locations spread across the United States. Siegel’s success was also tied to his expansion into related industries, such as real estate development, tourism, and hospitality.
The Queen of Versailles: Personal and Financial Struggles
David Siegel’s life took a dramatic turn when he and his wife, Jackie Siegel, became the subjects of the 2012 documentary The Queen of Versailles. The film, directed by Lauren Greenfield, chronicles the couple’s attempt to build the largest and most expensive single-family home in the United States—a 90,000-square-foot mansion modeled after the Palace of Versailles in France. The house, located in Windermere, Florida, became a symbol of Siegel’s immense wealth and ambition.
However, the 2008 financial crisis severely impacted Siegel’s business empire, and construction on the Versailles mansion came to a halt. Like many real estate investors during the recession, Siegel faced significant financial challenges as the timeshare industry struggled, and Westgate Resorts’ revenue plummeted. The company was forced to lay off thousands of employees, and Siegel had to make difficult decisions to keep his business afloat.
The documentary highlighted both the extravagance of the Siegels’ lifestyle and the very real financial pressures they faced. While some viewed the film as a cautionary tale of excess, Siegel himself was critical of how he was portrayed, calling the documentary biased and misleading.
Recovery and Continued Success
Despite the setbacks caused by the 2008 recession, David Siegel managed to steer Westgate Resorts through tough times and eventually rebuild his business. Over time, the timeshare industry rebounded, and Westgate Resorts regained its footing as a leader in the market. By 2013, Siegel was back on a growth trajectory, continuing to expand his business and invest in new properties.
One of his notable achievements was the acquisition of the Westgate Las Vegas Resort & Casino in 2014, a historic property previously known as the Las Vegas Hilton. This marked Siegel’s entry into the Las Vegas hospitality market, further diversifying his business interests.
In the years following the financial crisis, Siegel worked to restructure his company, reduce debt, and ensure its long-term stability. His perseverance in the face of financial adversity is often cited as one of his key traits as a businessman. Although the Versailles mansion project was delayed for years, construction eventually resumed, and the property remains a significant symbol of the Siegels’ larger-than-life persona.
Personal Life and Family
David Siegel has been married three times and has 11 children. His current wife, Jackie Siegel, whom he married in 2000, is a former beauty queen and socialite. Together, they have eight children, and Jackie is well-known for her appearances in The Queen of Versailles documentary and in various media outlets.
The Siegels’ family life has been marked by both opulence and tragedy. In 2015, their 18-year-old daughter, Victoria Siegel, passed away from a drug overdose, a devastating loss for the family. Following her death, David and Jackie became advocates for drug awareness and rehabilitation, working to prevent similar tragedies from affecting other families.
Controversies and Legal Battles
David Siegel’s career has not been without controversy. In 2008, he was involved in a high-profile lawsuit with his former employee, which accused him of wrongful termination and sexual harassment. The case was settled out of court, and Siegel denied any wrongdoing.
Siegel also became embroiled in political controversy when he claimed that President Barack Obama’s re-election in 2012 would hurt his business, even suggesting that he might have to lay off employees if Obama won. This statement sparked a media firestorm, though Siegel later clarified that he did not follow through with any mass layoffs after the election.
Philanthropy and Legacy
In addition to his business ventures, David Siegel has been involved in numerous philanthropic efforts. He has donated to various causes, including education, healthcare, and support for veterans. The Siegels have also been active in raising awareness about opioid addiction, following the loss of their daughter.
David Siegel’s legacy as a businessman is marked by his innovation in the timeshare industry and his resilience in the face of economic hardship. While his personal life has been the subject of intense media scrutiny, Siegel’s contributions to the real estate and tourism industries are undeniable.
Conclusion
David Alan Siegel’s life is a testament to the highs and lows of entrepreneurial success. From building a timeshare empire to facing financial collapse during the recession, Siegel’s journey has been one of perseverance, ambition, and larger-than-life dreams. Despite the controversies and personal challenges, Siegel remains a prominent figure in American business, continuing to shape the landscape of the hospitality industry.
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