Experience. Reputation. Teamwork.

Our law firm is local and multi-generational. Founded in 1991 by brothers Jamie Pressly and David Pressly, the firm has been serving the South Florida community for more than three decades. In 1999, Jamie’s son, Grier Pressly, joined the firm. The firm’s office managers are family members, too.

Although not members of the Pressly family, Attorneys John W. (“Randy”) Randolph, Jr., Katie Benjamin, and Jared Pape are essential members of the Pressly, Pressly, Randolph & Pressly team. Having served as the law firm’s first law clerk, Randy returned to the firm as an attorney in 2000 and has become a nationally-acclaimed estate planner. In 2016, Randy was made a name partner of the firm. Katie joined the firm in 2026 after 10 years as a partner with a local firm where she assisted high net worth families and business owners with their sophisticated estate planning strategies. Jared joined the firm in 2021 directly from the University of Florida law school’s JD/LL.M in Taxation joint degree program and has quickly developed into an experienced, highly-skilled tax and estate planning practitioner.

A cohesive unit, our lawyers work collaboratively to help you meet your litigation and planning goals. The lawyers of Pressly, Pressly, Randolph & Pressly are recognized leaders in their profession and in their community. Members of the firm have been elected as Fellows of the American College of Trust and Estate Counsel, a prestigious, invitation-only organization of recognized experts in the field of trusts and estates law. Members of the firm are also prolific authors and speakers in the field. Jamie and Grier are only the third father-son combination to serve as President of the Palm Beach County Bar Association in the 100-year history of the Bar. Our lawyers fill leadership positions on boards of local non-profits and in organizations that shape the practice of trust and estate law.

Accountable to you and to each other, family sets its own standard.