Mike Weinstein speaks about the Jacksonville Jaguars Stadium of the Future in May 2024. | Will Brown, Jacksonville Today
Published on December 15, 2025 at 12:40 pm
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Mike Weinstein, a longtime fixture in Jacksonville politics and government, has been appointed as the city’s chief administrative officer after the departure of Karen Bowling in October.
Mayor Donna Deegan announced his promotion in a news release Friday. Weinstein had served as Deegan’s chief of staff since September 2024.
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In her announcement, Deegan called the title change “just a formality,” explaining Weinstein had been working closely with Deputy Chief Administrative Officer Kelli O’Leary to manage city departments since Bowling’s unexpected resignation.
“Additionally, Mike will be available to me for Mayor’s Office priorities as I continue to evaluate our staffing needs,” Deegan wrote in the release.
The promotion puts Weinstein in the city’s top appointed position, responsible for supervising all departments heads and City Hall’s day-to-day operations.
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Before replacing Florida Blue North Florida Market President Darnell Smith as Deegan’s chief of staff, Weinstein was the lead negotiator for the mayor’s office during talks with the Jacksonville Jaguars on the $1.5 billion stadium renovation project.
Weinstein has been a presence in multiple mayoral administrations under Republicans and Democrat Deegan dating back to his time as chief of staff and city chief financial officer under then-Mayor Ed Austin.
Weinstein announced what would be a short-lived retirement from public service in September 2018, when he stepped down as chief financial officer under then Mayor Lenny Curry.
He later returned under Curry to become acting CEO of the city’s youth program organization Kids Hope Alliance.
A report in 2018 from Jacksonville Today news partner the Jacksonville Daily Record said Weinstein came to the city in 1975. He was an assistant state attorney and executive director of the 4th Judicial Circuit State Attorney’s Office and later represented Jacksonville in the state Legislature from 2008 to 2012, according to the Daily Record.
Weinstein also led Jacksonville’s host committee for Super Bowl XXXIX from 2000 to 2005 as president and CEO.
This will be the first time Weinstein has served as the city’s permanent top executive.
The city’s chief information officer, Phil Perry, tells Jacksonville Today that Weinstein’s salary will remain unchanged as he moves into his new role — $271,855 per year. Bowling left the role making $290,331 per year after starting the job at $275,000.
Bowling’s predecessor, Brian Hughes, who served as chief administrative officer under Curry, finished his tenure with a $330,977 annual salary.
Filling the chief vacancy
After Bowling’s official last day on Oct. 24, the city code gave Deegan 60 days to fill the vacancy for chief administrative officer.
Bowling also served as chief administrator under former Mayor Alvin Brown and was the University of North Florida’s first vice president of jobs. She was part of Deegan’s initial crop of 13 appointments shortly after her election in June 2023.
She resigned in a text message to the mayor which referenced a previous conversation.
“Mayor Deegan, per our conversation today please accept my resignation, effective October 24, 2025. Thank you for the opportunity and I wish you all the best!” the message provided at the time by Perry, says.
Deegan administration officials have never publicly discussed the reason for Bowling’s departure, but the mayor praised Bowling’s service after her resignation was announced.
The news of her departure brought praise for her work in the role from Jacksonville City Council members in both political parties.
