A legal dispute has arisen over the trust of David Siegel, the late founder of Westgate Resorts, following a lawsuit filed on June 24 in Orange County Circuit Court. The complaint, initiated by Siegel’s daughter-in-law, Janessa Siegel, on behalf of her two minor sons, alleges that they were improperly removed as beneficiaries by Michael Marder, the trustee and trust protector.
Janessa’s late husband, Steven Siegel—David Siegel’s son—passed away at the age of 63 from an incurable brain tumor. Steven served as Westgate’s senior vice president of sales before retiring in 2021. He married Janessa in 2015, and they had two sons together. Steven’s mother is Geraldine Spillers.
The complaint does not disclose the value of the irrevocable trust or specific details about its assets or beneficiary allocations. However, the case includes more than 30 defendants, including current and former Westgate executives and members of the Siegel family—such as Jackie Siegel, CEO Jim Gissy, former COO Mark Waltrip, and Marder, who also serves as outside general counsel for Westgate. Attorneys for the parties involved, as well as Jackie Siegel, have declined to comment to the Orlando Business Journal. A spokesperson for Westgate described the lawsuit as “frivolous,” labeling it a private family matter that will be “vigorously defended.”
At the core of Janessa Siegel’s claim is the assertion that the trust amendment, which removed her children as beneficiaries, was not properly witnessed or notarized, rendering it invalid. She also accuses Marder of breaching his fiduciary duty by simultaneously serving in the dual roles of trustee and trust protector, which she argues creates a conflict of interest. While Florida law permits one person to hold both positions, Geoff Hoatson, CEO of Family First Firm in Winter Park (who is not involved in the case), stated that such an arrangement is unusual and could compromise protections for beneficiaries.
Janessa is seeking Marder’s removal as trustee, reimbursement of legal fees, and a jury trial. On August 4, Marder filed a motion to transfer the case from civil court to the probate division; Janessa’s legal team opposed this transfer on August 7. Hoatson believes the matter will likely end up in probate court and, as is common with trust disputes, may ultimately be resolved outside of court.
Case Information
Case: Siegel, Janessa vs. Siegel, Jacqueline Mallery et al.
Number: 2025-CA-005979-O
Court: Circuit Court of the Ninth Judicial Circuit, Orange County
Judge: John E. Jordan
Attorneys: John McDermott (plaintiff); John Hart, Sarah Butters, Lynn Wright, Ira Spivey, Keith Durkin, Beth-Ann Krimsky (defendants)
