Jacksonville Republicans enter the 2027 election carrying political damage they helped create. Public feuds, a failed JEA board appointment and disputes within their own ranks have given opponents a record to attack. Democrats now bring substantial money, recognizable candidates and a recent countywide victory to that fight. The election will test whether Republicans have weakened the stronghold they spent years building.

Mayor Donna Deegan seeks reelection with roughly $2.4 million available across her campaign and supporting political committee. Moné Holder has already flipped a Republican-held countywide council seat. Basketball legend Artis Gilmore has entered the race against Council President Nick Howland. Those developments put more than the mayor’s office in play.

Steve Pajcic Finances Democratic Campaigns at Home and Across Four States

Jacksonville attorney and former Democratic state legislator Steve Pajcic is putting substantial money behind Democratic ambitions. The Magnolia Tribune, citing October reporting by The New York Times, reported that Pajcic and his children are spending at least $7 million through New Deal for All on Senate advertising in Florida, Kansas, Mississippi and South Carolina. The combined investment targets four states where Republicans traditionally hold the advantage. Pajcic is financing an effort to expand the Democratic map.

He is also backing Deegan’s current reelection effort. Duval for All lists $250,000 from Stephen Pajcic III, the attorney known as Steve Pajcic, and another $250,000 from Sallyn Pajcic. Florida Politics reported their combined $500,000 contribution in October 2025. That investment gives the mayor a substantial financial foundation for another campaign.

Steve Pajcic then contributed $510,000 to Jacksonville Together, the committee supporting Holder’s August special-election campaign. Holder won and took the At-Large Group 1 seat previously held by Republican Terrance Freeman. Her victory demonstrated that Democrats can pair substantial financial support with a successful countywide campaign. The Pajcic investments reach both the mayor’s office and the council that votes on her agenda.

Donna Deegan Holds Roughly $2.4 Million in Available Campaign Funds

Deegan already has the money to advertise, organize and answer attacks. Florida Politics reported October 14 that Duval for All held more than $2.2 million and her campaign account held almost $200,000. The committee update covered the reporting week ending October 2. Together, the accounts held roughly $2.4 million available to spend.

She also holds an early polling advantage. An August St. Pete Polls survey commissioned by Florida Politics put Deegan at 53% against Republican Wyman Duggan, a 20-point lead. The survey preceded Duggan’s October announcement, but it establishes the strong position from which she entered this stage of the race. Duggan must overcome both an incumbent’s financial resources and demonstrated voter support.

Duggan brings credentials and Republican institutional backing. The state representative and Florida House speaker pro tempore entered the race criticizing city spending and rising costs, while the Republican Party of Florida contributed $100,000 to his committee. He gives Republicans a serious challenger. He also faces an incumbent who has already won crossover support and built a well-financed political operation.

Ron Armstrong also continues to draw grassroots Republican support with a populist campaign built around community outreach, volunteers and a petition drive to qualify for the ballot. His supporters give the Republican field an active presence outside Duggan’s state-backed operation. Armstrong faces the same central obstacle: a well-funded incumbent with demonstrated voter appeal. Deegan’s roughly $2.4 million in available funds and early polling strength set a high bar for every challenger, including one campaigning on grassroots energy.

Artis Gilmore and Moné Holder Challenge Republican Countywide Control

Gilmore gives Democrats a challenger with recognition that most first-time candidates spend heavily to establish. The Jacksonville University basketball legend and professional Basketball Hall of Famer filed against Howland in At-Large Group 3. Voters across Jacksonville will decide that contest. Howland starts with substantial campaign resources and a record Gilmore must challenge.

Holder has already shown Democrats a path to winning countywide. Jimmy Peluso now seeks At-Large Group 4, the seat Republican Matt Carlucci must leave because of term limits. Those contests give Democrats opportunities to expand their representation beyond the mayor’s office. Republicans still hold 13 of the council’s 19 seats, but Democrats are challenging their control of the countywide positions.

Lisa Rinaman Brings an Established Civic Profile to District 7

St. Johns Riverkeeper Lisa Rinaman is running as a Democrat for District 7, which Peluso currently represents. She brings years of public advocacy and an established civic profile to the contest. The Riverkeeper organization announced that she will remain in that role through a transition ending in spring 2027.

A Rinaman victory would preserve a Democratic seat. Gilmore and Peluso seek seats Republicans currently hold. Together, the candidacies give Democrats a field that includes a sports icon, a sitting council member and a prominent environmental advocate.

Matt Carlucci Helped Elect Deegan, Then Fought Republican Colleagues

Matt Carlucci shows why Republican registration alone does not explain Jacksonville’s political divisions. He endorsed Democrat Donna Deegan in 2023, and his Next Generation Jax committee contributed $65,000 to Donna for Duval. He backed her with both his name and substantial political money. His support helped the Democratic candidate challenge the Republican nominee.

Carlucci then continued to challenge Republican colleagues and support prominent Deegan priorities. Supporters call that independence; critics call it disloyalty, captured in the label “Republican in name only.” His Republican affiliation gives those disputes the added force of criticism from within the majority. The party’s divisions play out in public with a Republican arguing against other Republicans.

He could advocate the same positions as a Democrat. Remaining a Republican changes the political effect: voters see members of the governing majority fighting one another. That does not establish why Carlucci retained his affiliation. It does explain why his critics regard his role as helping Deegan while undermining Republican unity.

Kevin Carrico’s JEA Controversy Damaged the Council’s Credibility

Kevin Carrico supplied opponents with a more serious issue than public infighting. In February 2026, the then-council president sought to replace JEA board member Arthur Adams with Paul Martinez, Carrico’s boss at the Boys & Girls Clubs of Northeast Florida. Text messages showed Carrico referring to a “big favor” and “my guy.” Martinez withdrew after the messages became public, and the State Attorney’s Office subpoenaed Carrico’s records. Carrico denied a quid pro quo and defended Martinez’s qualifications.

Carrico then raised allegations that JEA CEO Vickie Cavey presided over racism and a toxic workplace. On March 11, he created a council committee to investigate workplace complaints and potentially uncollected commercial capacity fees. The capacity-fee issue involved a separate inspector general inquiry. Its inclusion gave the committee a financial oversight assignment alongside the allegations against Cavey.

The later findings failed to substantiate the most serious workplace accusations. An outside investigation did not substantiate claims that Cavey created a toxic workplace, retaliated against employees or treated employees differently because of race. Reporting also described polarized employee views and a board recommendation for leadership training. The findings supported criticism of aspects of her management without validating the central accusations.

Cavey took medical leave in late July and resigned effective September 25. Deegan said politics had overtaken Cavey’s position, while JEA Board Chair M.G. Orender criticized the pressure surrounding her tenure and departure. Cavey described leaving as a personal decision for herself, her family and JEA. Her departure followed months of political conflict; she did not publicly identify that conflict as the definitive cause.

The sequence creates a credibility problem for Carrico. His own appointment drew scrutiny, then he shifted attention toward allegations against the utility’s chief executive. Voters can judge whether he exercised impartial oversight or turned his own controversy into a prolonged fight over someone else’s leadership. The timing warrants that scrutiny without proving retaliation. Then, Carrico announced his departure from the Boys & Girls Clubs of Northeast Florida.

Scott Wilson Challenged Carrico Before Carrico Abandoned Reelection

Scott Wilson made Carrico’s record an election issue before Carrico announced his departure. The former District 4 council member and past council president filed July 13. He attacked Carrico’s accessibility, criticized favor-based appointments and explicitly invoked the State Attorney investigation. On September 28, Carrico announced he would not seek reelection.

Carrico attributed his decision to a business venture with his wife, Daysi Jacobson Carrico. Alignment Global Partners combines tax expertise, executive leadership and business strategy, drawing on her accounting background. He had previously said he was likely to run again. He later said the couple had reconsidered their professional and family priorities.

The electoral context remains clear. Carrico won his 2023 full term without opposition; Wilson offered an experienced Republican challenger who attacked his controversies from the outset. Avoiding that contest offered a political benefit alongside Carrico’s stated business plans. Whether that benefit influenced his decision remains unconfirmed, but Wilson’s campaign established that dissatisfaction with Carrico extended inside his own party.

Public Feuds Give Voters Another Reason to Question City Hall

Rory Diamond and Jimmy Peluso have become prominent antagonists in disputes over JEA oversight. Peluso called the investigative committee’s work a “circus.” In a separate dispute, his request that Carrico temporarily relinquish the council presidency drew Carrico’s response calling him the council’s “biggest Drama Queen.” The exchanges turned questions of oversight and accountability into personal combat.

Carrico’s confrontation with Carlucci supplied another example. At a May 2025 meeting about changes to the Downtown Investment Authority, Carrico said he felt threatened when Carlucci approached and requested intervention by the sergeant at arms. Carlucci said he approached to explain that he was leaving early. The encounter put the Republican majority’s strained relationships on public display.

Democrats share responsibility when they join the feuding. Peluso’s countywide campaign puts his own judgment and conduct before a larger electorate. Voters can assess both the policy disputes and how the participants handled them. The public record gives challengers ample material to question the council’s professionalism.

Trump’s Unpopularity Threatens Republican Turnout as Democrats Gain on Affordability

Trump’s unpopularity creates a turnout risk for Republicans alongside an opening for Democrats on household costs. An October Reuters/Ipsos survey put his national approval at 32%. Pew Research Center also found a substantial enthusiasm gap: 63% of Democratic House candidate supporters described themselves as extremely motivated to vote, compared with 46% of Republican supporters. Those findings warn Republicans against assuming their voters will match Democratic intensity.

Democrats also enter this period with stronger economic credibility than they held in recent years. KFF’s October 6 poll report found voters trusted Democrats over Republicans on the cost of living, 39% to 25%, and health care costs, 42% to 22%. Gallup’s October 13 report found Americans favored Democrats over Republicans to keep the country prosperous, 51% to 37%. Just three years earlier, Republicans held a 14-point advantage on that Gallup measure.

For Jacksonville Republicans, the danger is a double hit: disappointed supporters stay home while Democrats turn affordability concerns into votes. A Republican voter does not have to support Deegan to help her win; sitting out also changes the electorate. These national midterm polls do not predict Jacksonville’s spring turnout, but they identify a risk local Republicans face. Deegan’s money and crossover appeal become more powerful if her opponents must also overcome an enthusiasm deficit.

Have Jacksonville Republicans Already Shot Themselves in the Foot?

Republicans have given their opponents a record that money alone cannot manufacture. The Carrico appointment controversy, the JEA leadership fight and repeated personal confrontations all unfolded while their party controlled the council. Wilson’s challenge showed that the backlash reached inside the Republican ranks. Carlucci’s support for Deegan and disputes with fellow Republicans further exposed the majority’s divisions.

Each official still owns an individual record. And in many ways Deegan has coopted the typical Republican agenda with her Cranes in the Air support for and from local development projects. And Deegan praised Howland and Finance Chair Will Lahnen for handling the September budget process, evidence that productive cooperation continues. But the party cannot erase the broader impressions. Deegan has roughly $2.4 million available, Pajcic has financed both her political operation and Holder’s successful campaign, and Gilmore has entered a major countywide contest. Democrats now have resources and candidates to exploit the weaknesses Republican actions have created. The election will measure how much those self-inflicted wounds matter.

As Democrats gain ground in 2027, Republicans will point to national politics, wealthy donors and crossover figures such as Carlucci. They should also examine the choices they made while holding power. Jacksonville Republicans have helped lay the groundwork for the gains they now hope to prevent.