JACKSONVILLE, Fla. — Jacksonville Mayor Donna Deegan announced Friday that Chief of Staff Mike Weinstein will formerly take over as the City’s Chief Administrative Officer.
In what the city called “just a formality” Weinstein has already spent the past two and a half months partnering closely with Deputy Chief Administrative Officer Kelli O’Leary to oversee city departments, following the resignation of former CAO Karen Bowling in October.
“Additionally, Mike will be available to me for Mayor’s Office priorities as I continue to evaluate our staffing needs,” Mayor Deegan said in a statement. “I am truly grateful for our entire team of dedicated public servants who have accomplished so much in such a short time for our citizens. Jacksonville has real momentum, and we’re keeping our foot on the gas to build an affordable, safe, and healthy city.”
Not everyone welcomed the announcement. City Council member Rory Diamond, a frequent critic of the Deegan administration, downplayed the decision, saying, “Yet another underwhelming move by Mayor Deegan. We need leaders for the future, not more failed retreads from the past. A real leader would have done a national search and brought the best to Jacksonville.”
Weinstein has a long, successful history in City government, including coming out of retirement twice to serve in various roles. Most notably of late, he was the architect of the Jaguars’ “Stadium of the Future” deal that will result in the city spending $775 million towards the renovation.
Bowling resigns as Chief Administrative Officer
A clear explanation for Bowling’s departure was never provided. However, Action News Jax’s Ben Becker learned that Bowling submitted her resignation via text message on Oct. 1, shortly after meeting with Deegan. Sources say both agreed during that meeting that it was time to “mutually go their separate ways.”
“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The leadership shake-up continued the same day of Bowling’s resignation as a job offer was withdrawn from former Jacksonville Bar Association Executive Director Craig Shoup, whom Bowling had previously recruited for a city role, according to Becker.
What’s Next?
Weinstein will make the same $271,855 salary as Bowling and will continue Chief of Staff duties as needed for the time being, according to a city spokesperson.
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