Before becoming a perennial candidate for mayor, Willie Wilson spent decades hosting Singsation, a Chicago gospel television show he launched in 1989. Wilson served as its host, producer and occasional performer.

Updated Chicago mayor rankings (ranked by likely to win): S tier: Alexi Giannoulias A tier: Susana Mendoza B tier: Brandon Johnson, Matt Brewer and Mike Quigley C tier: Maria Pappas, Lisa Nee and George Cardenas D tier: Joe Holberg, Willie Wilson and John Kelly E tier: Liam Stanton and Danni Carter

Willie Wilson just went on Facebook Live with a Willie Wilson portrait behind him and said he has a big announcement about the Chicago mayor race on Monday.

Two Chicago state senators are backing Alexi Giannoulias for mayor: • Sen. Javier Cervantes (1st) was at the Bronzeville launch yesterday wearing the campaign sticker • Sen. Lakesia Collins (5th) posted a endorsement on Instagram

Mike Quigley is not taking Alexi Giannoulias’s mayoral announcement too well, posting “Stop Wet TeeShirt” on Instagram.

Alexi Giannoulias launched his Chicago mayoral campaign with six aldermen in attendance: Brian Hopkins (2), Michelle Harris (8), Derrick Curtis (18), Felix Cardona (31), Emma Mitts (37) and Timmy Knudsen (43). Susana Mendoza had two aldermen at her launch; Mike Quigley had one.

Last night the Chicago Board of Education voted 11–7 to approve a ~$10 billion budget that CPS leaders warned is unbalanced. Yes votes came from Chicago Teachers Union aligned board members. The budget counts on $150 million in state funding that Springfield has not committed.

MAGA wants this guy to be mayor of Chicago but doesn’t know anything about our city. We’re a union town. Maybe this splits the cop vote and we’ll find out what’s more important to them, collective bargaining rights or open racism.

After some speculation, Bill Conway is not running for mayor of Chicago, and will instead run for re election as alderman of his downtown ward.

Same location. 6 days apart. Really shows how thick the smoke was in Chicago.

Big news in Chicago’s school board races: SEIU is officially lining up against CTU. CTU is backing its political director, Hilario Dominguez, while SEIU is supporting current school board member Jessica Biggs.

The Illinois State Board of Elections just voted unanimously to remove Chicago Ald. Byron Sigcho-Lopez and Mayra Macías from the IL-04 ballot after both fell short of the valid-signature requirement for independent candidates.

The 2027 Chicago mayor money race: Alexi Giannoulias — $21.8M John Kelly Jr. — $2.05M Susana Mendoza — $1.63M Bill Conway — $1.14M Joe Holberg — $1.04M Brandon Johnson — $631K Mike Quigley — $377K 2026 Q2 filings

NEW: Cook County inspector general report finds Commissioner Samantha Steele offered her primary opponent a job to drop out of the race, then lied to the media and refused to cooperate with investigators. She is directed to retake ethics training.

2027 Chicago Mayor Money Race End of Q2 2026 fundraising: 1. Alexi Giannoulias — $21.85M 💰🤑 2. John Kelly Jr. — $2.05M 3. Susana Mendoza — $1.63M 4. Bill Conway — $1.14M 5. Joe Holberg — $1.04M 6. Brandon Johnson — $631K The rest are under $400K

A state election hearing officer is recommending Chicago Ald. Byron Sigcho-Lopez be removed from the IL04 congressional ballot after he fell 1,222 valid signatures short. The Illinois State Board of Elections will later make the final decision.

A new UChicago Mansueto Institute poll finds Alexi Giannoulias generating the most excitement among likely Chicago voters for the 2027 mayoral race: Alexi Giannoulias 52% Susana Mendoza 47% Maria Pappas 40% Mike Quigley 33% Brandon Johnson 30%

A lot of people ask me "Is Willie Wilson running for mayor again?" I tell them probably. Well, he just loaned $100,000 to his campaign account called "Willie Wilson for Mayor 2027," so I just the answer is almost certainly "yes" now.

I respect France's commitment to not working on a holiday.

State Comptroller Susana Mendoza spent more than she raised in the quarter she entered the Chicago mayor’s race: $145K spent, $139K raised. And 72% of her haul came from one $100K contribution from Dan Webb. She closed the quarter with $1.6M cash on hand.

The Chicago Teachers Union is fielding candidates in just 13 of Chicago’s 20 school board districts. To win a majority on the school board, it must win 11 of those 13 races, 85%. Most of the South Side has no CTU endorsed candidate on the ballot.

I estimate Alexi Giannoulias’ Chicago only cable and network TV buy is at least $300,000, after analyzing public ad disclosures. The ad is for his Secretary of State reelection, but its timing, weeks before mayoral petitions, suggests City Hall ambitions.

After years of fighting for an elected Chicago school board, CTU has candidates on the ballot in only 13 of 20 district races (plus a write-in). It must win 11 of 13 races, 85%, to secure a majority on the board.

Operating Engineers Local 150 paid for this YouTube ad backing Alexi Giannoulias for Illinois Secretary of State. But it ran only in Chicago and is heavily Chicago themed, calling him “Chicago’s Answer.”

Just In: An Illinois election hearing officer recommends removing independent candidate Mayra Macias from the IL04 ballot after finding she failed to meet the 10,816-signature minimum. Macias is challenging Patty García, the heir apparent to retiring Congressman Chuy García.

The Nutella Cafe reopened today!

Cook County Treasurer Maria Pappas is giving away 100,000 bars of soap stamped: “Maria Pappas Mayor: Clean Up Chicago.” 🧼

Marty Quinn is super smart political guy. He was the brains behind the Madigan election machine during its heyday (his nickname was "The General." On Fran Spielman's podcast he predicts Chicago Mayor Brandon Johnson makes the runoff and will face either Alexi Giannoulias or Susana Mendoza.

Frank Calabrese @frankcalabrese.bsky.social · 4w ago

Alderman Marty Quinn told Fran Spielman he won’t seek reelection as alderman. Quinn was Michael Madigan’s hand-picked successor to run Chicago’s storied 13th Ward political organization and what remained of the Madigan machine. End of an era.

Alexi Giannoulias, rumored Chicago mayor candidate, just reported an additional $2.5 million in contributions. $1M came from billionaire Neil Bluhm and family: $500K from Neil Bluhm, $300K from JMB Realty, and $200K from son Andrew Bluhm.

Very saddened to hear about Russ Stewart’s passing. I started my political career on Chicago’s Northwest Side and Russ was one of the first journalists to use me as a source. Unfortunately, he was one of the last hyper-local political journalists. May he rest in peace.