What once looked like a relatively quiet reelection bid for Madison Mayor Satya Rhodes-Conway is quickly becoming a crowded race, with three challengers emerging ahead of the 2027 spring election.
Rhodes-Conway, who is seeking a third four-year term, will now face former Madison Common Council President Syed Abbas, former Alder Brian Benford, and One City Schools founder and CEO Kaleem Caire.
The rapidly growing field comes at a particularly difficult moment for the two-term mayor, who has faced criticism from across Madison’s political spectrum over her handling of the fallout from the fatal police shooting of Corey Ruiz and the protests that followed.
Satya Rhodes-Conway
Rhodes-Conway announced her reelection campaign in July, pitching a third term as an opportunity to continue her work on housing, transportation, climate initiatives, and the city’s rapid growth.
The incumbent entered the race with significant high-profile support, both from the progressive wing of her party as well as the Democrat establishment. Her campaign has touted endorsements from Gov. Tony Evers, U.S. Sen. Tammy Baldwin, Congressman Mark Pocan, and Dane County Executive Melissa Agard. Then-Democratic gubernatorial candidate and Madison-area State Rep. Francesca Hong also appeared at Rhodes-Conway’s July campaign launch to endorse her.
But the political environment surrounding Rhodes-Conway has changed considerably since that announcement.
The July 22 fatal police shooting of Corey Ruiz sparked weeks of protests and the creation of an encampment around the intersection of Williamson and Baldwin streets. As the occupation continued, nearby businesses and residents increasingly complained about its impact, while city officials raised concerns about safety and access.
Rhodes-Conway initially resisted calls for an immediate crackdown, giving demonstrators nearly two weeks before ordering the streets cleared on Aug. 4. Police ultimately arrested more than 20 people amid confrontations surrounding the removal.
That approach earned Rhodes-Conway criticism from both directions.
Residents, businesses, and critics of the encampment questioned why the city allowed the situation to persist for as long as it did. Progressive activists, meanwhile, blasted Rhodes-Conway for ultimately clearing the site. Protesters later demonstrated outside the mayor’s home after the removal.
Rhodes-Conway herself acknowledged the political crossfire, saying critics on one side wanted the city to shut down the protests immediately while others wanted the encampment permitted to remain indefinitely.
In 2023, Rhodes-Conway defeated Madison Metropolitan School Board Member Gloria Reyes, receiving 55% of the vote.
Syed Abbas
Former Madison Common Council President Syed Abbas entered the race this week, bringing both local and state government experience to his challenge against Rhodes-Conway.
Abbas was first elected to the Common Council in 2019 and served as both vice president and president during his two terms. He left the council after unsuccessfully seeking a State Assembly seat in 2022, losing the Democratic primary to Melissa Ratcliff, who now serves in the State Senate.
Since 2024, Abbas has worked at the Wisconsin Department of Health Services under the Evers administration, currently serving as deputy legislative director.
Abbas has already signaled that he plans to make Rhodes-Conway’s leadership and community engagement central issues in the race. In announcing his campaign, he argued Madison needs a mayor who can bring people together and make city government more responsive.
His early platform includes seeking legislative approval for a half-percent local sales tax (similar to what Milwaukee County Executive David Crowley and Milwaukee Mayor Cavalier Johnson received in Act 12), reviewing the city budget for efficiencies, pursuing public-private partnerships to increase housing development, and creating a community intervention office within the mayor’s office.
Kaleem Caire
The newest entrant into the race is Kaleem Caire, founder and CEO of One City Schools, adding a longtime Madison education and community leader to the increasingly crowded field.
Caire founded One City Schools in 2014. The organization operates a preschool as well as independent public charter elementary and middle schools and serves hundreds of Madison-area students.
His candidacy comes as One City is itself in the middle of a potentially significant transition. The Madison Metropolitan School District Board recently voted 6-0 to advance One City’s initial charter application, beginning a process that could eventually bring the schools into a formal partnership with MMSD.
Caire also brings a lengthy resume in Madison civic and education circles. Before founding One City, he served as president and CEO of the Urban League of Greater Madison and previously worked for organizations involved in education reform at both the state and national levels.
Brian Benford
Former Madison Alder Brian Benford is also mounting a challenge, launching a campaign explicitly focused on racial disparities and the city’s response to the Ruiz shooting.
Benford, a longtime community activist who previously served on the Common Council, announced his campaign Tuesday while sharply criticizing Madison’s political leadership in the aftermath of Ruiz’s death.
Benford said the events of the past several weeks had exposed what he views as deeper problems with racial inequality and city leadership, arguing that Madison needs leaders willing to confront those issues with greater empathy and accountability.
His entrance makes the Ruiz controversy more than simply a vulnerability Rhodes-Conway will have to defend on the campaign trail. It is now a central rationale behind at least one opponent’s decision to run.
With more than five months remaining before the February primary, the four-way field creates an unusually competitive environment for an incumbent mayor who won reelection comfortably four years ago.
And with challengers approaching Rhodes-Conway from different corners of Madison’s overwhelmingly Democratic political landscape, the race could become an early test of whether the coalition that twice elected her mayor remains intact after a turbulent summer at City Hall.
