Chicago Contrarian, The Podcast

Chicago Contrarian, The Podcast

A summary conversation on news events and public affairs in Chicago.

Episodes

October 17, 2026 • 68 mins

After decades of fiscal recklessness, aldermen in the City Council passed an ordinance raising the benchmark to approve borrowing. Will the mayor pass it? Chicago shells out $260M in police settlements. CPS enrollment dropped by another 11K. What drives this enrollment? We'll discuss.

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Today, our host Jim Bosco, Paul Vallas, and I sat down with Don Tracy as he nears election day to discuss his campaign against Juliana Stratton.

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CTU political director and candidate for the Board of
Education is in a spot of trouble, again. Mayor
Johnson is signaling his intent to raise the Head Tax,
and others to close an $882M budget gap. Will he
face opposition in Council? In three weeks, voters
will head to the polls to send a new senator to
Capitol Hill. We'll discuss.

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After decades of fiscal recklessness, aldermen in the City Council passed an ordinance raising the benchmark to approve borrowing. Will the mayor pass it? Chicago shells out $260M in police settlements. CPS enrollment dropped by another 11K. What drives this enrollment? We'll discuss.

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After a lengthy debate, Chicago has approved the sale of city parking meters to a NY investment firm. How does Chicago benefit? This week, Mayor Johnson proposed a moratorium on data centers within city limits. What motivates this proposal? Board of Education elections are 40 days away. We'll discuss the four candidates for president.

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In a widely expected announcement, Mayor Johnson declared his intent to seek a second term. How well did the mayor state his case for a second term?

The City Council Finance Cmte. approved two settlements this week, one of which was $13.7M to two men originally convicted for a heinous murder in 1998. Why is Chicago prepared to hand over millions to two men Kim Foxx admitted were likely guilty?

 Mayor Johnson's PRO Act narrowly...

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In the next installment in our series interviewing mayoral candidates, our panel sits with George Cardenas to learn his plan for Chicago.

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September 12, 2026 • 65 mins

City lawyers are recommending a $13,75M settlement for two men accused in a grisly double murder. Do two men Kim Foxx believed committed this crime deserve millions? A third alderman has decided to call it quits. How will this affect upcoming City Council elections? Chicago media delivered a blitz of coverage marking the anniversary of Operation Midway Blitz. Was it overdone, media bias or necessary coverage? We'll di...

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In a lengthy discussion with host Jim Bosco, Comptroller Susana Mendoza sat for an interview on her campaign for mayor and her vision for Chicago.

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A proposal to swap the Amtrack yard and build a new stadium for the Chicago White Sox is in the works. What is the impact on Bridgeport? Mayor Johnson announced an $882M budget deficit for FY 2027. Can the mayor pull a rabbit out of the hat to close this yawning deficit without raising property taxes or layoffs?

Another mass shooting took place in Washington Park. Mayor Johnson's response was discouraging. We'll discuss.

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The race for president of the Board of Education thinned this week as Jenny Custer dropped out. What are the implications of Custer leaving the contest? Mayor Johnson says he has a solution for Chicago's budget crisis. Johnson, thus far, has only blamed moderate Dem. aldermen.

Another divorce record has been unsealed. In this instance, BOE candidate Victor Henderson is fighting allegations of abuse. We'll discuss.

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Today, our host interviews John Kelly, lobbyist and candidate for mayor of Chicago.

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A cartoon and criticism of the CTU has inspired the great minds at the union to strike back. The union filed a lawsuit against its arch-nemeses, IPI, Liberty Justice Center, and Austin Berg. Why? WIll this case go anywhere? Tolls will dramatically rise next year, due to Pritzker's tollway board. Is this necessary or another Pritzker tax? 25th Ward alderman, Byron Sigcho Lopez, faced scrutiny this week over the unsealing of his divo...

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After a surge of law enforcement on CTA trains, City Hall and the CTA rolled out a new pilot which includes CVIs and mental health experts on trains. The Chicago Bears held a press conference to update Chicago on its plans to build a stadium. Will the Bears leave? Countering their erstwhile friends, the CTU, the SEIU unveiled its endorsements and donations to BOE candidates. What will the SEIU's impact be on the elect...

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As expected, Secretary of State Alexi Giannoulias entered the 2027 mayoral race. Behind him is $22M in campaign funds. What does Alexi bring to the race? A former CPS official has been nabbed in a PPP scandal. A NBC5 investigation has revealed the CTU's coveted "sustainable community school" model is a failure. We'll discuss.

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In a wide-ranging interview, Chicago Flips Red co-founder and mayoral candidate Danielle Carter-Walters sits down with Contrarian's panel to discuss her campaign.

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Mayor Brandon Johnson signed off on another Executive Order on gun violence. What is the mayor seeking to accomplish by setting "standards" for purchase rather than removing criminals from the streets?

 In what could be a last hurrah for the CTU, the CPS budget was passed by an 11-7 vote. What is in or not in it? The AFT filed a lawsuit against Cook County Treasurer Maria Pappas. Is there merit to the suit or is it the CTU usi...

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The CTU's bargaining unit was certified by the Chicago News Guild. Why would a union representing journalists form an alliance with the teacher's union? The Bombastic Alderman Byron Sigcho Lopez was dismissed as an Independent candidate for the 4th congressional district race. Sigcho Lopez claims "democracy died" when he was tossed off the ballot. Was the ruling unfair or is BSL just facing rules his own party put into place? We'll...

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In a wide-ranging interview with Contrarian, former Superintendent of Police Eddie Johnson discusses crime, police recruitment, teen takeovers, political influence over policing in Chicago, and his career with the Chicago Police Departmen

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A U of C poll reveals Mayor Johnson's dim reelection prospects. Which mayoral candidate is setting the world on fire? The CPS has laid off over 1,500 employees. Was this necessary? How will these layoffs impact the CPS budget? November Board of Education races are on the horizon. CTU will not have candidates in every race. Is the CTU facing its Waterloo? We'll discuss.

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