Legacy Planning Law Group

We're There for Your Family When You Can't Be

Bill O’Leary, Esq., Attorney at Law

As an estate and elder planning attorney, Bill is passionate about making the planning process understandable and comfortable.  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 guides clients through a process that many find daunting and unfamiliar. Planning for death and disability often is ignored and, sadly in far too many situations, it is never done because people find the process mysterious, intimidating and overwhelming. Bill identifies a client’s concerns and journeys with them through the process. Just as he wants to be guided and treated in unfamiliar situations, Bill makes sure that his clients understand what is going on as they develop a plan that embodies their unique wishes and desires.

As Bill has moved along the continuum of life and increasingly embraced the long view, he has come to appreciate the importance of legacy and family harmony. Bill’s clients are no different. Bill helps clients implement their own personalized plan that reflects what is important to them. A good estate and elder plan is so much more than deciding who gets what; it is a legacy planning tool where family values and traditions are handed down to the next generation and the family treasure isn’t lost to devastating cost of long-term care. A well thought-out plan promotes family harmony. A good plan also makes sure the family is taken care of when the client can’t do so anymore. It is most gratifying to see clients achieve peace of mind knowing their family is safe and protected and their family story is preserved. Bill very much believes in the firm motto, “We Take Care of Your Family When You Can’t Anymore.”

Good estate and elder planning is not a ‘one-size-fits-all’ proposition.  No two families are alike. Each plan is customized to the client’s unique needs. Each client is given personal attention. Communication 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. Phone calls are returned promptly and top-quality legal documents are delivered on a timely basis. Bill treats clients with dignity and respect and strives to create a warm and memorable client experience. The bottom line is that Bill treats clients in the same manner he would want to be treated.

Estate planning is not a one-time transaction. It is a lifelong process that adapts as a client’s family dynamics change. Bill aspires to have his clients see him as their trusted advisor for life, walking with them every step of the way.

Bill has been married to his bride and love of his life, Joan, for 31 years. 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. Will is in his last year of law school at the University of Florida law school.  Bill and Joan could not be any more proud of Caroline and Will.

Bill and Joan attend St. Joseph’s Catholic Church 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. As Bill likes to say, “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, Board of Directors
  • Society of Financial Service Professionals of Northeast Florida, Board of Directors
  • Estate Planning Council of Northeast Florida
  • Small Business Resource Network