Siegel was born to a Jewish family in Chicago, to Sadelle and Sid Siegel, a grocer, who moved the family and grocery business to Miami in 1945. Siegel grew up in Florida where he graduated from Miami Senior High School in 1953, and later studied marketing and management at the University of Miami, before dropping out. In March 1961, Siegel married Geraldine Florence Sanstrom. The couple had three children. Their marriage ended in 1968. In 1970, Siegel married Betty Tucker and moved from Miami to Orlando. They divorced in 1997 and he remained the custodial parent of all the children. He met his current wife Jackie Siegel in 1998. Although she was not Jewish, they married in a Jewish ceremony. Siegel's businesses, family, and personal life were adversely affected by the 2008 financial crisis, as seen in the documentary The Queen of Versailles. On June 6, 2015, the Siegels' 18-year-old daughter Victoria Siegel was found unresponsive at their home in Windermere, and after being taken to hospital, was pronounced dead. The cause of death was later determined to be a drug overdose, which motivated him to advocate against drug abuse.
Politics
Siegel campaigned for George W. Bush in 2000. In a February 2012 interview by Susan Berfield, Siegel elaborated: During the 2012 United States elections, Siegel caused controversy and public debate when he sent a mass email to his employees, suggesting that they vote for Republican Party candidate Mitt Romney or he might have to take drastic measures in how he operated the company. In January 2015, it was noted that his company had experienced "the best year in our history" and he raised his company's minimum wage to $10 per hour.
Sexual harassment lawsuit by Dawn Myers
In 2008, Siegel was found liable in a sexual-harassment lawsuit brought by former Westgate employee Dawn Myers. After a trial in the United States District Court for the Middle District of Florida, the jury awarded $5.4 million, but the judge reduced the award to $610,000. In the trial award, Myers recovered $103,622.09 in compensatory damages and $506,847.75 in punitive damages arising from her claim of battery under state law, but her claims of sexual harassment were found to be time-barred. The United States Court of Appeals for the Eleventh Circuit dismissed an appeal and cross-appeal, affirming the district court's judgment.
''The Queen of Versailles''
The Queen of Versailles is an award-winning 2012 American documentary film by Lauren Greenfield. The film shows Jackie Siegel and David Siegel, owners of Westgate Resorts, and their family as they attempt to build the Versailles house, the largest and most expensive single-family house in the United States, and the crisis they face as the U.S. economy declines. The film also shows Siegel trying and failing to retain ownership of Westgate's Las Vegas high-rise resort, the PH Towers Westgate. Siegel's son and senior Westgate executive, Richard, is quoted as saying that David Siegel's determination not to lose the Ph Tower was a major source of the company's financial troubles in 2009–11. On November 22, 2011, a controlling interest in the property was sold to Resort Finance America LLC. On January 10, 2012, David Siegel and Westgate Resorts, Ltd filed a lawsuit in Florida against the Sundance Institute and the filmmakers of The Queen of Versailles, claiming that Sundance's published film description was defamatory. On January 23, 2013, the United States District Court JudgeConway of the Middle District of Florida ordered a stay of the lawsuit pending arbitration. In her order, Judge Conway called the testimony previously offered by Mr. Siegel during court hearings "inconsistent and incredible and thus lacking weight". The matter was subsequently heard before an arbitrator for the Independent Film & Television Alliance in June 2013. On March 13, 2014, the arbitrator awarded in favor of the filmmakers, Lauren Greenfield and Frank Evers, including an order that David Siegel and Westgate Resort pay $750,000 to the filmmakers. The arbitrator wrote in the award, "Having viewed the supposedly egregious portions of the Motion Picture numerous times, simply does not find that any of the content of the Motion Picture was false." The arbitrator also wrote that Westgate had failed to show how it was damaged from the documentary. Finally, the arbitrator wrote that Westgate "did not remotely establish the type of malice required for a defamation claim on behalf of a public figure." A second lawsuit filed by David Siegel in February 2013, against the filmmakers of The Queen of Versailles, was subsequently heard by Greg Derin of the American Arbitration Association in Los Angeles. On February 28, 2014, Derin ruled that the filmmakers' agreement with the family, pertaining to certain life rights, was "invalid and unenforceable". The Siegels' attempt to sue for $5 million in damages was also dismissed by Derin.
Siegel was one of the founders of Mystery Fun House which was an attraction in Orlando, Florida which opened on March 28, 1976 and operated until 2001. It was located near International Drive, on Major Boulevard just across from Universal Orlando Resort. Over time, the fun house expanded to include a laser-tag facility, an arcade, a dinosaur-themed mini golf course and other attractions. He also produced a movie within the MFH called in 2002. It starred local talent but also included Jeff Speakman and Al Lewis.