• Carson Gaines

Meet Our [Law] Suits: Gypsy Bailey


Gypsy Bailey is the Bar's General Counsel
Gypsy Bailey

Gypsy Bailey, General Counsel and Director of Ethics and Consumer Protection for The Florida Bar, has been familiar with the field of law since a young age. Born and raised in the small town of Marianna, Florida, Gypsy grew up watching her father work as a lawyer, admiring the level of care he showed for his clients. These memories from childhood had such an impact on Gypsy that they served as the focal point of her personal statement when she applied to the Florida State University College of Law.


Gypsy Bailey being held by her dad when she was a baby.
Gypsy Bailey and her dad.

Specifically, Gypsy focused on the parallels she saw between her father and arguably fiction’s most beloved lawyer, Atticus Finch. Like Finch, Gypsy’s father would allow low-income clients to pay for legal services with food or other goods, which her father would find on the front porch of his office across the street from the courthouse. His generosity and respect for clients inspires Gypsy to this day.


Upon graduating with honors from the Florida State University College of Law, Gypsy accepted a position with the Florida Office of the Attorney General, where she worked for over seven years, spending most of her time on criminal and capital appeals. Several years later, Gypsy would settle into the position of General Counsel for the Leon County Clerk of the Circuit Court and Comptroller, serving in this position representing the County Clerk in legal matters for almost 20 years.


An employee at The Florida Bar since spring of 2019, Gypsy spends her time working on many different issues which, at the moment, includes reviewing mandatory bar issues and responding in prisoner litigation. Gypsy has also recently completed an online non-profit management course through Duke University. When asked what she enjoys the most about working at The Florida Bar, Gypsy says she loves the great team with whom she has the pleasure of working. She also has a special love for mastering new information and then training others on what she has learned.


When discussing the importance of professionalism and civility, Gypsy immediately thinks of retired Second Circuit judge Terry Lewis. Gypsy admired that Judge Lewis was never visibly ruffled in the courtroom and was fair and judicious. She has always strived to apply this level of professionalism to her career, being courteous and friendly with opposing counsel and using a calm demeanor regardless of circumstances.


Outside of work, Gypsy loves spending time with her two sons, William and Daniel. Seemingly inspired by their mother, William is an attorney working as a bar prep tutor, while Daniel is currently experiencing the joys of LSAT prep. Gypsy is also an avid reader and a self-described “sci-fi nerd,” an obsession which started in 9th grade after reading Dune by Frank Herbert and that continues to this day. Another fun fact about Gypsy is that she is musically talented, knowing how to play the clarinet, bassoon, and classical piano.


As our conversation closed, Gypsy made a point to note how much she genuinely enjoys her work as it always presents her with engrossing problems that allow her to make a difference. Gypsy then went on to say that a large part of her enjoyment at The Florida Bar comes from the opportunity to work with the great co-workers she has, learning from them and using that knowledge in the many unique issues presented every day.


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