Diana C. Chestnut, Esq.


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Diana C. Chestnut, Esq. is an attorney at Davis Law Firm specializing in insurance coverage and business litigation. Before joining Davis Law Firm, Diana practiced appellate law followed by non-profit disaster litigation after Hurricane Michael ravaged the panhandle. Diana then moved to the private sector to litigate workplace discrimination claims.

As a legal aid attorney, Diana served on the state-wide committee for Landlord Tenant Law and was one of the first attorneys in Florida to litigate the COVID-19 eviction moratorium. Diana assisted with drafting proposed legislation at nationwide conferences on disaster response and, as the first Disaster Response Attorney in the state, shaped the processes from which the Governor modeled his formation of a disaster response coordination team.

Diana graduated Cum Laude from Florida Coastal School of Law, on Dean’s List, and with numerous book awards. Diana won best Best Oralist in Moot Court, where she competed in several nationwide competitions and was selected as a student clerk for the Honorable Judge Brian Davis, U.S. District Court for the Middle District of Florida. She also served as the Vice President of the Academic Honors Society and participated in the first Appellate Clinic sponsored by the law school.

Prior to her legal career, Diana worked as a Child Protection Investigator and Juvenile Diversion Services Case Manager. During Graduate School at Jacksonville University, Diana worked for the Mayor of Jacksonville, serving on the Juvenile Justice Subcommittee and evaluating the effectiveness of the Jax Journey Program. As the Graduate Assistant for the Public Policy Institute, she created the framework for a Policy Journal, graduated in the top of her class, and won Graduate Student Woman of the Year.

Bar Admissions

  • The Florida Bar
  • U.S. District Court for the Southern District of Florida


  • Florida Coastal School of Law, Jacksonville, Florida
    • Juris Doctorate, Cum Laude
    • Moot Court, Best Oralist
    • Academic Honors Society, Vice President

  • Jacksonville University, Jacksonville, Florida
    • Master of Public Policy, Magna Cum Laude
    • Graduate Assistant

  • University of South Florida, Tampa, Florida
    • Bachelor of Social Work, Honors
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