St. Johns County Court Judge Casey L. Woolsey was elected to the bench in 2023. She currently hears criminal and civil cases at the Richard O. Watson Judicial Center in St. Augustine.
Tell me about your professional background and career.
I’m a county court judge here in St. Johns County, Florida. Before I took the bench, I practiced law for over a decade, primarily handling criminal and civil litigation and trial work. I earned my undergraduate degree from the Georgia Southern University and went on to earn my law degree from Florida Coastal University.
Before becoming a judge, I co-owned and operated a private law firm with my husband, where I had the chance to work in criminal and civil litigation, serving as counsel to individuals and businesses. That hands-on courtroom experience, coupled with my work advising clients in a wide range of legal areas, gave me a solid foundation for the work I do now as a judge.
Was there a point in your life where you discovered an interest in the law, or have you always wanted to work in the legal system?
I’ve wanted to be a lawyer for as long as I can remember. I grew up in a military family, and during one of my dad’s deployments, my mom faced a legal issue with our housing that was overwhelming and confusing. An Army JAG officer stepped in to help her navigate it — and I still remember the calm and confidence she brought into our home. Watching someone use their knowledge of the law to bring clarity, comfort and fairness to a difficult situation left a lasting impression on me.
That was the moment I understood the real impact the legal system could have — not just in courtrooms, but in people’s everyday lives. From then on, I was drawn to the law. I saw it as the ultimate way to serve others.
What do you like most about what you do?
What I love most is the opportunity to make processes better — not just for the court system, but for the people who have to navigate it. I love looking for ways to improve access, make procedures more efficient and ensure fairness for everyone who comes through my courtroom.
There’s also something deeply meaningful about being a calm and steady presence in a system that can feel overwhelming for people. I try to bring humanity, patience and clarity to every case, whether it’s a landlord-tenant dispute, a criminal matter or anything in-between.
Do you have any personal or professional accolades or achievements you would like to share?
Graduating from Leadership St. Johns in 2021 was a highlight, both professionally and personally. It deepened my understanding of the needs and strengths of our community and introduced me to a network of incredible leaders. I also enjoy participating in a Jacksonville Area Legal Aid event every year where several of us ride our bicycles from the St. Johns County Courthouse to the Jacksonville Courthouse to raise money for legal aid initiatives in our community.
Can you tell us about your family?
I’m the proud mom of four boys. They keep me on my toes, laughing, learning and occasionally scrubbing permanent marker off the walls. Being their mom is my greatest joy and the most important job I’ll ever have.
My husband, Josh, is an attorney and business owner. We ran our law practice together for many years before I joined the bench, and now he manages the firm while also staying active in community nonprofit work and kids’ sports. We make a good team, and we try to instill in our boys the same values that drive us: service, integrity and hard work.
You are involved in your community and charitable endeavors. Tell me a little about this and what motivates you to contribute to these various causes or issues.
I believe public service doesn’t end at the courtroom door. I’m active in local legal and educational groups including an advisory board of a local high school academy and the local bar associations and Inns of Court.
I also try to stay active in civic and school-related groups; I’ve served on committees at my kids’ school and I’ve volunteered for local mentorship, leadership and legal education programs. Contributing to the community is not only part of my role but also a key aspect of the person I strive to be for both my community and my children.
Are you from this area originally?
I’m not originally from here. I grew up in a military family, so I’ve lived all over the country. That experience gave me a deep appreciation for community and stability. My husband and I each came to this area separately for law school, and once we got to know the people, the pace and the potential of this community, we knew it was exactly where we wanted to build our life. It was the clear choice for where we wanted to start our careers, raise our family and put down roots.
What do you like best about living in this area?
The sense of community. There is collective dedication in making things better, whether it’s our schools, our courts or our neighborhoods. We’ve also got historic charm, gorgeous beaches and growing, vibrant energy. But it still feels like a small town in all the best ways.
How do you like to spend your free time?
Spending time with my family is always my first choice. You’ll usually find us out in the community cheering on our boys at local flag football games on Fridays and Saturdays or at EverBank Stadium on Sundays if the Jaguars are playing at home. We love being outside together, whether it’s riding bikes through our neighborhood, playing pickleball with friends or supporting local events. This community has so much to offer for families, and we try to take advantage of it as much as we can.
