The Life and Times of David A Siegel

David A. Siegel was a renowned American businessman, best known for being the founder and former CEO of Westgate Resorts. He was born in 1954.

Siegel's business career began in the 1970s, and he founded Westgate Resorts in 1982. The company has since grown to become one of the largest timeshare companies in the world.

Siegel's success was not limited to his business ventures, as he was also a philanthropist. He donated millions of dollars to various charitable causes throughout his life.

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David A. Siegel's career is a testament to his entrepreneurial spirit and ability to adapt to changing times. He co-founded Mystery Fun House in Orlando, Florida, which opened on March 28, 1976, and operated until 2001.

The fun house expanded to include a laser-tag facility, an arcade, and a dinosaur-themed mini golf course. This eclectic mix of attractions was a hallmark of Siegel's ability to think outside the box.

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Siegel also produced the movie Night Terror in 2002, which starred local talent and notable actors Jeff Speakman and Al Lewis (The Munsters). This venture showcased his interest in the entertainment industry.

In 1982, Siegel founded Westgate Resorts with the opening of a 16-unit resort at Westgate Vacation Villas in Kissimmee, Florida. Under his leadership, the company grew into the largest privately held timeshare company in the world.

Siegel's family and personal life were featured in the 2012 documentary The Queen of Versailles, directed by Lauren Greenfield. This film highlighted the financial challenges faced by Westgate Resorts during the 2008 financial crisis.

Here's a list of some of the notable films and TV shows David A. Siegel has been involved in:

David A. Siegel was born to a Jewish family in Chicago, and later moved to Miami with his family and grocery business in 1945.

He grew up in Florida, graduating from Miami Senior High School in 1953.

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Siegel studied marketing and management at the University of Miami, but dropped out.

In March 1961, Siegel married Geraldine Florence Sanstrom, with whom he had three children.

Their marriage ended in 1968, and in 1970, Siegel married Betty Tucker, moving to Orlando.

The couple divorced in 1997, with Siegel remaining the custodial parent of their children.

In 1998, Siegel met his current wife Jackie Siegel, whom he married in a Jewish ceremony despite her not being Jewish.

The 2008 financial crisis had a significant impact on Siegel's businesses, family, and personal life, as seen in the documentary The Queen of Versailles.

On June 6, 2015, Siegel's 18-year-old daughter Victoria Siegel was found unresponsive at their home in Windermere, and was later pronounced dead due to a drug overdose.

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David A. Siegel has been involved in several controversies throughout his life. In 2008, he was named in a sexual harassment lawsuit filed by a Westgate former employee.

The lawsuit was covered by various media outlets, and in 2012, a jury awarded the plaintiff damages. Siegel denied the allegations.

A defamation lawsuit filed by Siegel and Westgate Resorts against the Sundance Institute and the filmmakers was stayed and later resolved through arbitration. The arbitrator ruled in favor of the filmmakers, finding no falsehoods in the film and awarding them $750,000.

Siegel was named in a 2008 sexual harassment lawsuit filed by a former Westgate employee, which was covered by various media outlets.

The plaintiff was awarded damages by a jury in 2012, although Siegel denied the allegations.

A defamation lawsuit was filed by Siegel and Westgate Resorts against the Sundance Institute and the filmmakers in 2012, which was stayed and later resolved through arbitration.

The arbitrator ruled in favor of the filmmakers in 2014, finding no falsehoods in the film and awarding them $750,000.

A separate lawsuit by David and Jackie Siegel regarding life rights was also dismissed.

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David Siegel, the founder of Westgate Resorts, passed away on April 5, 2025, at the age of 89, after a bout with cancer.

He was married to Jacqueline and had 13 children, including 12 grandchildren and step-grandchildren.

David's entrepreneurial spirit led him to start Westgate Resorts in 1982 with just one property on an orange grove he owned in Kissimmee, Florida.

Over the years, he built the company into the largest privately held timeshare company in the world, with over 13,500 rooms at 22 resorts across the United States.

David's legacy extends beyond his business accomplishments, as he created thousands of jobs and became one of the largest private employers in Central Florida.

He was a devoted husband and father, and his family was a priority in his life, as evident from the fact that he remained the custodial parent of all his children after his divorce in 1997.

David's impact on the community was recognized through various awards, including an honorary doctorate from Florida A&M University and the Ernst & Young's Entrepreneur of the Year for the State of Florida.

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