It’s already a crowded field!
“I’m running!” educator Kaleem Caire told The Werkes. “Will announce on September 15 and am inviting everyone who wants to be there for it. … It’s time!”
Kaleem founded One City Schools in 2014 as an independent school chartered by the University of Wisconsin Office of Educational Opportunity after the Madison school board refused to sanction his proposed charter high school as a “non-instrumentality charter” (meaning not subject to the teachers union contract) 15 years ago.
He was president and CEO of the Urban League of Greater Madison (2010-2014). Ran for Madison school board in 2019 but lost. Grew up on Madison’s south side.
The incumbent, Satya Rhodes Conway, has already announced her bid for a third term. Sensing vulnerability, challengers are coming in hot and heavy. Former alder Brian Benford announced earlier this week. Former alder Syed Mustajab Abbas has held meet and greets for mayor but has not formally announced.. Former county supervisor April Kiyega is rumored. We think Francesca Hong runs for mayor.
One City educates 491 children from pre-school through middle school on a portion of the former campus. One City Schools is asking the public school district to absorb it for the 2028-29 school year.
Blaska’s Bottom Line: Kaleem Caire is the most serious challenger to Mayor Satya — not only to date but likely for good this election cycle. The election is eight months off in April 2027, likely after a primary election in February.
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