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Bill O’Leary is passionate about making the planning process easy, comfortable, and understandable. He has dedicated his legal career to helping families achieve the peace and calm that comes with planning well, finishing the race strong, and leaving a lasting legacy built on family harmony.

Bill understands that good estate and elder planning is not a ‘one-size-fits-all’ proposition. No two families are alike. As a dedicated Jacksonville estate planning attorney, Bill customizes each plan to the client’s unique needs and provides each client personal attention. Communication with his Jacksonville area clients is clear and in plain English. Once Bill learns a client’s specific goals and desires, he sets out options and makes recommendations that are simple and understandable. Book your free call to discuss your planning dreams and desires with Bill today!

“It’s not whether you get knocked down; it’s whether you get up.”

-Vince Lombardi

Get to Know Bill


Jacksonville Estate and Elder Planning Lawyer Bill O’Leary has personal experience that good planning works. His parents saw the wisdom of good advanced planning and set up their estate plan years ago in the way they wanted. When his mother was diagnosed with Alzheimer’s, their advanced planning served her well because everything was already set in place in a way that would lighten the burden on the family and encourage unity among the children. Bill’s father doesn’t need to worry about how to pay for long-term care because they had planned ahead. Instead, Bill was able to focus on providing his parents with care and companionship. The wise planning done by Bill’s parents years earlier eliminated a lot of potential stress and anxiety. Bill has seen first-hand the many benefits of good planning and he wants to deliver that peace of mind to his Jacksonville and Northeast Florida clients.

Bill has been married to his bride and the love of his life, Joan, for 32 years. Joan is a dermatologist with her own medical practice in Orange Park. Bill and Joan have two wonderful adult children, Caroline and Will. Caroline married another Irishman, John McKinney. While Bill likes to joke around with John, he couldn’t be a better son-in-law. Caroline is a licensed neurologic physical therapist working in the Brooks Rehabilitation system. Will is a recent law school graduate from the University of Florida College of Law and is currently clerking for a federal district court judge in Miami. Bill and Joan are tremendously proud of Caroline and Will.

Bill and Joan attend St. Joseph’s Catholic Church in Jacksonville where they are active in several ministries. Bill and Joan enjoy traveling and spending time with Caroline and Will. Bill also has a bit of an unusual hobby, he umpires high school baseball. It serves as a great release from the office. Bill likes to say about being an umpire, “It’s the best seat in the house!”


  • Georgetown University, B.A. (1984)
  • Temple University School of Law, J.D. (1988)
  • University of Florida College of Law, Graduate Tax Program, LL.M (Taxation) (2012)

Professional Associations

  • Florida Bar (Real Property, Probate and Trust Law Section; Elder Law Section; Tax Law Section)
  • Financial Planning Association of Northeast Florida, former President and member of the Board of Directors
  • NAIFA of Northeast Florida, member of the Board of Directors
  • Spina Bifida of Jacksonville, member of the Board of Directors
  • Planned Giving Council of Northeast Florida
  • Estate Planning Council of Northeast Florida
  • Academy of Special Needs Planners
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