Meadow at Blaska Experimental Work Farm

Kaleem Caire is running for mayor of Madison

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.

Kaleem Caire

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 announced Tuesday 08-25-26. 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.

Think he has a chance?

Take me back home, Jeeves!

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7 responses to “Kaleem Caire is running for mayor of Madison”

  1. Jon Burack Avatar
    Jon Burack

    Can he pull it off? Can Madison yet rise from the ashes? “They say the darkest hour is right before the dawn.” Sometimes it’s even true.

    Reply
  2. One Eye Avatar
    One Eye

    Nope. Not until he disavows this (he’s a board member):

    Reverend David Hart released a statement regarding the shooting.

    “Corey Ruiz was a human being with a family and a community that loved him,” said Rev. David Hart for BPSA of Dane County. “True public safety cannot exist when officers act as judge, jury, and executioner in our streets. We demand full transparency, swift administrative termination, and absolute accountability through every available legal channel.”

    (From wmtv15).

    NO ONE running to the left of Satya has a snowball’s chance in hell. These candidates all need to realize the average Madison liberal is not going to fall for the racial grifting anymore.

    Reply
  3. One Eye Avatar
    One Eye

    And of course the guy who created a charter school is a non-starter in Madison. I doubt his campaign survives to September 15.

    Reply
  4. One Eye Avatar
    One Eye

    Uh oh strike 3 – Reddit thread on mayoral candidates links to this post. Blaska expressing any hope for a candidate dooms said candidate. Don’t take it personally. Mayor Dave recently said if he had endorsed Kelda it would only have hurt her. Same with Paul Soglin.

    Old white guys can’t win. It’s ageist, racist and sexist.

    Unfair but it is what it is.

    Kaleem’s mayoral run is going to be shorter than Bud Fox’s executive career at Bluestar Airlines.

    Reply
  5. Bob Avatar
    Bob

    Not a chance. Doesn’t have enough boxes checked and MMSD and MTI hate him.

    Reply
  6. fjaeckle Avatar
    fjaeckle

    He has my vote for those considered to be likely candidates at this time. My vote could change if someone I feel is a better candidate announces.

    Reply
  7. Bill Bass Avatar
    Bill Bass

    Hide the credit cards

    Reply

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