David Lillesand

David Lillesand has represented over 3,500 clients with SSI disability claims in ALJ hearings, federal court, and the U.S. Circuit Court of Appeals, and assisted individuals to become financially eligible for means-tested benefits through Special Needs Trusts, ABLE accounts, ISM Contracts, and other permissible spend-down alternatives.
He got his bachelor’s degree from the University of Minnesota and graduated from the University of Wisconsin Law School, was a Peace Corps and VISTA volunteer and then worked in legal services programs for seven years before establishing his firm, Lillesand, Wolasky & Hitchcock, P.L. in Miami and Tampa, Florida.
David frequently lectures at law schools and state bar associations around the country, and trains trust officers on SSI and SNTs at some of the nation’s largest financial institutions. He is the author of the chapter on Special Needs Trusts in the Lexis/Nexus publication, Administration of Trusts in Florida (10 th ed. 2022). His analysis of the impact of Obamacare on SSA disability claims and Special Needs Law was published in Forbes.com.
David received the Florida Bar Elder Law Section’s Lifetime Achievement Award, the ARC Plotkin Outstanding Legal Service Award for service to persons with intellectual and developmental disabilities and the Florida Bar President’s Pro Bono Award.
David is trilingual, speaking English, Spanish and POMS (the SSA staff manual), and to his wife’s amazement, he accurately reads IKEA without leaving any extra pieces behind. He is many-decades married to Dr. Diane Lillesand, a retired Clinical and Forensic Psychologist, who secured a second master’s degree in Buddhism and a second Ph.D. in Hinduism just for retirement fun. His daughter, Jessica, graduated law school magna cum laude and has an LL.M. in Tax Law from NYU, and formerly worked for Wells Fargo Private Bank and Sabal Trust Company but beat her dad to retirement in 2019.