JACKSONVILLE, Fla. — The Mayor’s Office is denying that the sudden withdrawal of a city job offer to former Jacksonville Bar Association Executive Director Craig Shoup was connected to the resignation of Chief Administrative Officer Karen Bowling, who recruited him for the city role, according to Action News Jax’s Ben Becker.
Shoup, who had served with the JBA since 2017, was offered the position of Neighborhoods Administrator on September 12.
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In an offer letter obtained by Becker, which was signed by the city’s human resources manager, Shoup was promised a $125,000 annual salary, a start date of October 13, and a direct report to Neighborhoods Department Director Thomas Waters.
Shoup accepted, resigned from the Bar Association effective October 10, and according to sources, even completed employee orientation, including having his badge photo taken.
On Wednesday night, however, he received a phone message informing him that the city was rescinding the offer, effectively being fired via voicemail before he even started.
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The decision came just hours after Bowling submitted her resignation to Jacksonville Mayor Donna Deegan. Bowling’s departure is effective October 24.
A clear explanation for Bowling’s resignation was not provided at first, but Becker learned Bowling left her $290,000 per year position via a text on October 1. It was sent to Deegan soon after the two had met, and where sources say both agreed to mutually go their separate ways. Becker is working to confirm more details on what led to the split. Here is what the text said:
“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!”
Adding to the uncertainty, the Jacksonville Daily Record published an article Thursday morning written by Shoup announcing his departure from the JBA, an article that had already gone to print before he received word that the offer had been pulled.
Mayor’s Office Response
Asked by Becker whether Bowling’s resignation played a role in the city’s reversal, a spokesperson for Deegan denied there was a connection.
“We are going in a different direction with the position that Mr. Shoup applied for. Reevaluation of roles and structure sometimes happen in organizations with thousands of employees. It is unrelated to CAO Bowling stepping down,” the Mayor’s Office said.
Becker asked in a follow-up email what the reevaluation of roles and structures was that necessitated pulling the offer 18 days later, and the spokesperson only offered “We don’t have additional comment on the matter.”
Timing of decision
The development comes at a politically sensitive time for City Hall. The Mayor and the Republican-led City Council just went through a contentious budget process, including the finance committee stripping nearly $445,000 from the Mayor’s Office budget. The salaries of Bowling and Shoup, both Republicans, total $415,000.
“These events and amounts are not connected,” said the Mayor’s Office Spokesman.
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Deegan also removed Shoup from the board of the now since troubled Jacksonville Housing Authority in August 2023 and attempted to replace him with Sulzbacher Center CEO Cindy Funkhouser but it was subsequently blocked by HUD because Sulzbacher receives federal funding.
Shoup backed Fackler… and Deegan
In January, the Jacksonville Bar Association, under Shoup’s leadership, issued a strong defense of City General Counsel Michael Fackler after a resolution of “no confidence” was filed against him by Councilman Ron Salem, who incidentally is a long-time friend of Shoup.
“The duly appointed General Counsel enjoys the respect of the Jacksonville legal community and has earned his reputation as a highly skilled lawyer,” the Association wrote in a statement.
The resolution stemmed from a series of high-profile disputes between City Council and Fackler, where legislators felt Fackler was biased towards Deegan, including his legal opinion that Deegan had the authority to remove Jacksonville’s last Confederate monument, and his determination that the council overstepped its authority in approving a multimillion-dollar waste contract increase.
What’s next?
Shoup’s future plans remain uncertain, but the JBA has named Jon McGowan as its interim Executive Director.
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