Former Florida Blue executive Darnell Smith will return to a role as Jacksonville Mayor Donna Deegan’s chief of staff, a city spokesperson confirmed Aug. 10.
Smith held the same position in 2023 and 2024 before he was replaced by Mike Weinstein, who is now Deegan’s chief administrative officer. During his first stint as chief of staff, Smith served as an executive on loan through a contract between the city and Florida Blue, with the company covering his salary and benefits.
Smith announced in February he was retiring as North Florida market president for Florida Blue.
“Darnell is the rare type of leader who brings decades of executive experience combined with genuine humility and an unending desire to help people,” Deegan said in a news release announcing Smith’s return. “Jacksonville is a city on the rise, and we’ll only climb higher with Darnell returning to lead our talented team.”
In the release, Smith said he was grateful for the chance to “continue serving our city and building on the momentum that Mayor Deegan has created.”
“It’s an honor to be part of a team that is working to make Jacksonville safer, healthier, and more affordable for everyone,” he said.
Phil Perry, the city’s spokesperson, said Smith’s addition was the only recent change in Deegan’s executive office.
Smith, who began his role Aug. 10, fills a position that had been vacant since December 2025, when Weinstein moved from chief of staff to CAO.
Weinstein replaced former CAO Karen Bowling, who resigned from her role with the city in October 2025. Bowling is now the CEO of WareWorks Skilled Trades Institute.
With Florida Blue, Smith was responsible for the company’s market growth and community involvement across 36 North Florida counties. Previously, he served as Florida Blue’s Group vice president over service organization and business process management organization.
Smith was cochair of Deegan’s transition team after she was elected in 2023. He has served on the boards of Sulzbacher, Cathedral Arts Project, First Coast YMCA, LIFT JAX, JAX Chamber, JAXUSA Policy Council, United Way of Northeast Florida, A.L. Lewis Black Opportunity and Impact Fund and Blue Zones Jacksonville.