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William O'Leary

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William O'LearyPractice Areas

Bill O’Leary concentrates his practice in the areas of trust and estate planning, business succession and legacy planning, probate and estate administration, lifetime giving and charitable planning, and incapacity and special needs planning. Bill represents a wide variety of clients with diverse planning and administration needs. Representation includes clients with estate plans from the simplest to the more elaborate, including wills, revocable living trusts, credit shelter or “bypass” trusts, generation-skipping or “dynasty” trusts, qualified personal residence trusts, and charitable trusts.  He also prepares pre-nuptial and post-nuptial agreements as part of a broader estate and asset protection plan.

Bill advises clients on the tax consequences of proposed transactions, including estate, gift, generation-skipping and income taxes. He counsels owners of closely held businesses on succession planning, business formation and governance issues, income tax planning, and the sale or disposition of the business. He also represents beneficiaries and fiduciaries in various kinds of estate and trust administration and litigation, including will and trust contests.

Practice Philosophy

Bill designs comprehensive estate plans based on the personal priorities, family situations and financial positions of his clients, with the goal of securing and protecting their hard-earned wealth and financial future.

Estate planning ensures the assets family members worked so hard accumulating during life are protected and distributed to those they love after their death. Bill strives to develop plans that reduce tax liabilities, limit expenses associated with estate administration, and minimize the possibility of costly litigation between beneficiaries. The objective is to make sure the client’s estate is handled promptly, efficiently, cost-effectively, and with minimal or no probate or other court involvement, all while minimizing or eliminating estate and other transfer taxes.

He guides his clients through the process of developing clearly-worded estate planning documents that communicate the client's preferences during life and upon death.  Sound estate planning is not a one-size-fits-all proposition. No two people, no two families and no two estates are the same—Bill O’Leary understands this fact and customizes each estate plan to his client’s unique needs.

Bill views estate and trust planning, not as a one-time transaction; rather, a life-long process that must change as a client’s assets and family dynamics change, in addition to reacting to the inevitable changes in the law. A well thought-through estate plan adds to his clients’ lives and the lives of their families. Bill’s professional goal is that his clients see him not only as their estate planning lawyer but as their life-long, trusted advisor.


Bill completed his undergraduate studies in 1984 at Georgetown University where he received a Bachelor of Arts degree in political science. He attended law school at the Temple University School of Law where be obtained his Juris Doctor degree in 1988. Rounding out his legal education, he received a postgraduate law degree in taxation, known as a “Master of Laws” or LL.M degree, from the prestigious Graduate Tax Program at the University of Florida’s College of Law in 2012.

Experience and Community Involvement

Bill launched his legal career working as a young lawyer in Philadelphia before moving with his family to Jacksonville in 1993 to work at Rogers Towers, P.A. where he became partner in 1998. He took a hiatus from practicing law in 2004 to start a commercial real estate development business. Seeing the need for businesses and families to develop and maintain strong succession or estate plans, he returned to law in 2011, first obtaining an LL.M law degree in taxation before joining Glazier & Glazier, P.A. in 2012.

Bill is an active member of the Florida Bar Association where he serves on various committees of the Real Property, Probate and Trust Law Section and the Tax Section. He also is active in the Trust and Probate Section of the Jacksonville Bar Association. Bill is a member of the Estate Planning Council of Northeast Florida, the Small Business Resource Network, Rotary Club of Mandarin, and the Southside Businessmen’s Club.

Member of the Small Business Resource Network - The SBRN helps businesses succeed by connecting them with interested, experienced service providers and government agencies.