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Regina D. Ross has a diverse legal career, starting as a Judicial Law Clerk at the United States District Court for the Middle District of Florida in 2004. Regina D. then transitioned to become the Deputy County Attorney for St. Johns County, Florida in 2007, where they served until 2021. In 2021, they took on the role of Chief Legal Officer at JEA.

Regina D. Ross holds a Bachelor's Degree in Economics from the University of Florida, obtained between 1988 and 1993. Regina D. then pursued a Master of Public Administration (MPA) at Valdosta State University from 1995 to 1997. Subsequently, they attended Penn State Law from 2000 to 2003, earning a Juris Doctor (J.D.) degree in Law. In 2015, they obtained certification as a Board Certified in City County and Local Government Law from The Florida Bar, in addition to their Bar Admission from both The Florida Bar in 2003 and the United States District Court for the Middle District of Florida.