The bitter race to serve the remainder of Terrence Freeman’s at-large Jacksonville City Council term has attracted large campaign checks and been marred by lawsuits as Democrats hope to chip away at the council’s super-majority Republican voting bloc.

Republican Deborah Wesley, Democrat Moné Holder, and Libertarian Addison “Liberty” Patrick are all on the ballot for City Council At-Large Group 1 seat, left vacant as Freeman pursues a state House seat. All of the council’s five at-large seats are held by Republicans, but Democrats are betting big that the seat can be flipped.

Steve Pajcic, a top backer of Mayor Donna Deegan, has poured $300,000 into the race as a loan to the Jacksonville Together political committee, which is supporting Holder’s bid. Most of that money has been spent.

The committee’s chair, Robyn Sieron, said Pajcic, a trial lawyer and longtime Democratic donor, was “furious” after the City Council tried to cut $1.9 million last year from Meals for Wheels, which his late wife volunteered with for decades (the council later restored a chunk of the program’s funding).

Wesley, a retired Jacksonville Sheriff’s Office commander, has nearly raised $95,000 and spent around $20,000, according to campaign finance records, and the Building a Stronger Jacksonville political committee has spent another $10,000. Her donors include City Council members Joe Carlucci, Kevin Carrico, Terrence Freeman, Mike Gay, and Rory Diamond’s political committee. She also had an early backer in her former boss, Jacksonville Sheriff T.K. Waters.

Unless one of the candidates receives more than 50 percent of the vote in the Aug. 18 primary election, two candidates will head to a runoff election in November. As of Aug. 12, Democrats were outpacing Republicans in mail-in and early voting, with Democrats casting 50 percent of the 40,000 votes already cast.

After Patrick, the Libertarian candidate, staved off a Republican attempt to remove her from the ballot, Wesley now faces a residency challenge that a judge will hear on Friday. Wesley’s lawyer denies that she lives outside the required group area. While the five at-large council members represent the entirety of Jacksonville, the candidates must live within five distinct areas to run.

Holder — the chief advocacy and political officer with Florida Rising and current chair of the Jacksonville Planning Commission — is endorsed by the council’s Democratic minority.

“When I’m elected, my plan is to work with or attempt to work with everyone across the aisle,” Holder told the Florida Trib about working with the Republican majority. “Because for me, it’s not about partisanship; it’s about Jacksonville and making Jacksonville a world-class city.”

Wesley initially agreed to an interview with the Florida Trib but did not respond to efforts to set one up ahead of deadline. Wesley also agreed to participate in a WJCT roundtable with Holder and Patrick but ultimately backed out.

Holder, who previously worked as a legislative aide in the Florida State House, wants to prioritize investing in affordable housing, public safety, and infrastructure upgrades like sidewalks, parks, and drainage. She said her time on the Planning Commission as a Deegan appointee working with constituents on issues affecting neighborhoods prepares her for the council. Holder is the current commission chair.

“I’m prepared day one to hit the ground running. My two opponents, they have respectable backgrounds in their own right, neither of which have the educational and the practical experience to on day one move policy for the city,” Holder said.

Duval GOP fails to kick Libertarian off ballot

The Republican Party of Duval County initially sued Patrick to keep her off the ballot in June, claiming she was not a member of the Libertarian Party for the minimum year before the primary election’s qualifying period, per a new Florida state law. A judge dismissed the case, saying the law does not affect special elections.

“At first glance, you would think, why would the GOP even bother suing a third-party candidate, a Libertarian candidate who has very little funds in comparison?” Patrick told the Florida Trib. “They are scared because in this area, not all areas, but in this area, people see Libertarians historically as Republican lite.”

In a counterclaim, Patrick alleges that Wesley does not live within Group 1’s boundaries, which a judge dismissed.

Patrick, a frequent commenter at city council, said that she does not support the property tax referendum and thinks the city needs to “press pause” on developments and “roll back” on spending.

Patrick has spent nearly all of $5,700 donated to her campaign.

“I want to show to the everyday person in Jacksonville that you don’t have to have a fancy job title, and you shouldn’t have to be wealthy in order to run for local office, you shouldn’t be buying an election,” Patrick said in an interview. “Both sides of the aisle are very authoritarian. Both sides like to tell people what to do, and I don’t like to be told what to do.”

New residency claims against Wesley

After a judge dismissed Patrick’s residency claims against Wesley, former Democratic candidate James Eddy filed a separate lawsuit in late July against Wesley, whose address listed in court dockets is on Amber Ridge Road, located in at-large group 5. Wesley’s summons was delivered to an apartment at Integra River Run, ten minutes north of the Amber Ridge Road address.

Using JEA electricity bills filed in court, Eddy claims Wesley did not live at the Integra Drive apartment for the required six months to be on the ballot. Patrick joined his suit as a third party Wednesday.

Wesley kept possession of the Amber Ridge Road property after her 2024 divorce, according to Duval County court records, which Eddy’s lawsuit cites.

“These desperate claims have already been rejected by the courts twice and dismissed with prejudice,” her campaign said in a statement. “This is the same tired playbook of the radical left: launching baseless political attacks against Republican candidates, particularly when that candidate happens to be a person of color.”

Molly Farrar is a Report for America corps member and the Florida Trib’s Jacksonville municipal watchdog reporter. She can be reached at molly.farrar@floridatrib.org.