The trust of David Siegel — whose exploits as a Central Florida businessman, philanthropist and husband fueled extensive media coverage, a movie and a soon-to-come Broadway show — is locked in a legal battle with Siegel’s daughter-in-law, who claims her two young sons were unfairly deprived of their share of the late timeshare mogul’s fortune.
Janessa Siegel filed a lawsuit in June in Orange County Circuit Court decrying the young boys’ “reckless omission” from Siegel’s trust. They and their father Steven Siegel were removed as beneficiaries in 2023, the year before Steven Siegel’s death.
The lawsuit fingers Michael Marder, David Siegel’s longtime attorney and overseer of his trust. Marder says in court documents he made the change in the trust at David Siegel’s behest.
The conflict features a rich cast of characters.
David Siegel founded and built Westgate Resorts into a sprawling timeshare resort conglomerate. He is perhaps best-known, however, for efforts with his third wife Jacqueline to build a 90,000-square-foot mansion called Versailles House in the exclusive Lake Butler Sound community, on Kirkstone Lane near Windermere. It became the subject of Lauren Greenfield’s 2012 documentary, “The Queen of Versailles.”
David Siegel had 13 children, as well as 12 grandchildren and step-grandchildren. He died in April of this year at 89.
Steven Siegel, the son of David Siegel’s first wife Geraldine, had worked closely with his father at Westgate, eventually becoming the company’s senior vice president of sales before retiring in July 2021, around the time he was diagnosed with a brain tumor, according to his obituary. He died last October at the age of 63.
Janessa Siegel, 38, is Steven Siegel’s second wife. She’s a University of Central Florida graduate and realtor, according to the website for the Orlando brokerage company where she works. Her biography also boasts about her travels to more than 75 countries and “the most exotic locales on the planet,” and touts her familial connection to David Siegel, saying she “knows luxury real estate.” She’s now attending law school, her social media pages show.
David Siegel, president and CEO of Westgate Resorts, in 2014. (Jeff Scheid/Las Vegas Review-Journal/TNS)
It’s unclear why David Siegel would have wanted to keep Steven Siegel’s youngest sons out of the trust, but court documents indicate he gave a lot of money to the family while his son was alive. In addition to employing Steven Siegel, David Siegel gave his son and his daughter-in-law money to purchase their home, according to an email Marder wrote to Janessa Siegel and her attorneys in February 2025. Janessa Siegel lives in a five-bedroom, 8,000-square-foot home just down the road from the famous “Versailles House,” property records show. She and Steven Siegel purchased the home for $3.8 million in 2020.
The cash infusion continued after Steven Siegel became ill, as David Siegel provided “millions in financial support,” to the family, according to Marder’s email.
“This included his full salary and all living expenses over and above his salary,” Marder wrote. “This included mortgage payments, household expenses, nannies and worldwide travel, home renovations, automobiles and lavish credit card spending.”
The message, provided as an exhibit in court documents, apparently was in response to questions from Janessa Siegel’s attorneys, though it’s not clear what they asked.
Marder declined to comment on the suit, saying he couldn’t discuss pending litigation “except to say that the matter will be vigorously defended,” and Janessa Siegel’s attorneys did not respond to an email this week from the Orlando Sentinel.
Janessa Siegel’s legal argument hinges on propriety of Marder’s change to David Siegel’s trust. As a trustee, he was obligated to act impartially in the best interest of the beneficiaries, the lawsuit argues, and Marder “violated his fiduciary duties,” because he failed to do so.
Marder wrote in an affidavit that he removed Steven Siegel and, subsequently, his two youngest children, as beneficiaries of the trust in July 2023. That change “accurately reflects” David Siegel’s intent, he wrote.
Steven Siegel was married twice and had five children. His first wife was the mother of his two oldest sons, who are adults, as well as a daughter, who died as an infant. They divorced in 2014. He married Janessa Siegel in 2015 and the pair “travelled extensively and had many adventures as newlyweds and new parents,” according to Steven Siegel’s obituary.
One of Central Florida’s wealthiest individuals, David Siegel established Westgate Resorts in his garage in 1982 with its first property on an orange grove he owned in Kissimmee. Over the next several decades, the company grew exponentially, billing itself as the largest privately held timeshare business in the world and one of the largest resort developers in the United States, boasting more than 13,500 rooms at 22 resorts across the country.
He retired as CEO in March, the month before his death, and was succeeded by Jim Gissy, a close friend and self-described right-hand. Gissy, his children and his grandaughter also are named as beneficiaries in Siegel’s trust.
Jackie Siegel, wife of Westgate Resorts CEO David Siegel, stands in the unfinished grand ballroom of her dream mansion named Versailles in Windermere, Florida July 27, 2012. The Siegels were the subject of the documentary film “The Queen of Versailles” that documented their life as they constructed their 90,000 square-foot dream mansion in the middle of the real-estate crisis. Picture taken July 27, 2012. REUTERS/David Manning
Despite his passing, David Siegel remains a subject of interest beyond the local courts. A musical based on Greenfield’s film, also called “The Queen of Versailles,” premiered last year in Boston, Massachusetts, starring Oscar winner F. Murray Abraham as David Siegel and Kristin Chenoweth as Jacqueline Siegel. Previews of the Broadway show are slated to start Oct. 8, with an official opening date set for November.
anmartin@orlandosentinel.com
