10 Things You Didn’t Know About David Siegel

The name David Siegel is frequently associated with success, luxury, and entrepreneurship. Known primarily for his time as the CEO and founder of Westgate Resorts Ltd., one of the biggest resort developers in the world, Siegel’s name often evokes images of opulence. But how much do we really know about him? In this article, we delve deeper into the life and character of this intriguing entrepreneur.

1. Humble Beginnings

Despite the luxurious life that Siegel now enjoys, his beginnings were much more humble. Born in 1935 in Chicago, Illinois, he was raised in a housing project during the Great Depression. His parents were grocers, a job that Siegel initially followed before embarking on his delivery business and then real estate.

Interestingly, his first try at business was unsuccessful. He had bought a foreclosed property and tried to lease it out but ended in financial ruin. However, he bounced back and created Westgate Resorts Ltd., which would be the platform that propelled him to global recognition.

2. Highschool Dropout

Despite being labeled as a high school dropout, Siegel managed to carve a grand name for himself in the business world. While studying in high school, he began working for his family’s grocery store. This early exposure to business management would later inform his decisions when establishing Westgate.

His lack of formal education never stopped him from making intelligent decisions in business. Siegel credits his hands-on approach to learning as providing him the necessary skills to navigate the murky waters of property development and management.

3. Westgate Resorts Ltd.

Westgate Resorts Ltd, which Siegel founded in 1970, grew steadily over the years to become one of the leading vacation ownership companies worldwide. The company which started with only a single 16-unit resort complex in Kissimmee, Florida has expanded into much more.

Westgate Resorts now has a grand portfolio of 28 full-service resorts spread out across the U.S. The rise of Westgate Resorts is a significant testament to Siegel’s entrepreneurial prowess and strategic acumen.

4. Documentary Participation

In addition to his accomplishments in business, David Siegel also shared his life’s ups and downs in a compelling documentary, “The Queen of Versailles”. The documentary which was released in 2012, featured the life of Siegel’s family during the 2008 financial crisis and how it affected their plan to build the ‘largest mansion in America’.

The documentary made significant waves upon its release, gaining laurels from various film festivals and receiving critical acclaim. It shed light not only on the Siegel’s extravagant lifestyle but also on their struggle to maintain their vast wealth amidst economic uncertainties.

5. Philanthropist

David and his wife, Jackie Siegel, are also known for their philanthropic activities. Their charitable endeavors include the Westgate Resorts Foundation which focuses on providing support to the Central Florida community including scholarships, grants and employee assistance programs.

Since their daughter Victoria’s untimely passing in 2015 due to a drug overdose, they have become vocal about the importance of proper education about drug misuse and addiction. The Siegels have used their platform to address this particularly through the Victoria Siegel Foundation.

6. Pageant Affiliations

Siegel has a noted affinity for beauty pageants. In fact, his wife Jackie was the winner of the Miss Florida USA pageant in 1993. They continue to show support for such events and have cosponsored Miss Florida USA for several years.

Moreover, Mrs. Siegel has been appearing as a judge in several beauty pageants and their home in Windermere has been the site for the filming of Miss Florida USA.

7. Legal Battles

With massive wealth and properties comes legal issues. Over the years, Siegel has had his fair share of legal battles to protect his empire. For instance, the release of the documentary, “The Queen of Versailles” led to a defamation lawsuit against the filmmaker, which was later dismissed by the court.

Siegel and Westgate Resorts have also faced a number of lawsuits in connection with their timeshare operations. Despite these challenges, Siegel has managed to keep his business afloat and thriving.

8. The Largest Mansion in America

One of Siegel’s most audacious projects is the construction of the largest mansion in America, a project that began in 2004. Codenamed “Versailles”, the finished project is designed to have nine kitchens, a two-story movie theatre, a bowling alley, a skating rink, and more.

However, the construction underwent several challenges including the financial crisis in 2008. The project was put on hold and the unfinished property was put on the market. The construction resumed in 2013 and as of 2018, is said to be 70% complete.

9. Siegel’s Political Side

Siegel is known to have significant influence in politics given his contributions to various campaigns. In 2012, he made headlines for an email he sent to his employees hinting that voting for Barack Obama could potentially result in job losses in their company. This move was met with both criticism and support.

Despite controversies, Siegel was steadfast in expressing his political views and in using his influence to support political agendas.

10. Personal Life and Tragedy

David Siegel is a father of eight children, most having been born from his marriage to Jackie Siegel. The Siegel family experienced a tragic loss in 2015 when their 18-year-old daughter Victoria was found dead due to a drug overdose.

This unfortunate event drove the family to advocate for drug addiction awareness. They believe in turning this tragedy into a meaningful legacy to help others that are struggling with addiction.

In conclusion, David Siegel is a man of many facets: business tycoon, flamboyant character, doting father and much more. His life story is an archetype of the American Dream – from rags to riches.

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Victoria Siegel Foundation