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Chicago Contrarian, The Podcast

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Rating
★★★★☆
4.2
from
14 reviews
This podcast has
73 episodes
Language
English
Explicit
No
Date created
2025/08/17
Latest episode
2026/10/17
Average duration
75 min.
Release period
5 days

Description

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

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Check latest episodes from Chicago Contrarian, The Podcast podcast


City Council attempts to rein in spending, Foxx's shadow looms over Chicago, CPS enrollment drops, again.
2026/10/17
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.
U.S. Senate candidate, Don Tracy.
2026/10/16
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.
Hilario in trouble, more taxes from City Hall, Senate race.
2026/10/10
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.
City Council attempts to rein in spending, Foxx's shadow looms over Chicago, CPS enrollment drops, again.
2026/10/03
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.
Parking meters, data centers, Board of Education elections.
2026/09/26
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.
Johnson announces, aldermen wilt, the PRO Act.
2026/09/19
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 passed out of the City Council's Housing Cmte. Under Johnson's version, a "tenant database" will be created. Is this bill helping renters or assailing landlords? We'll discuss
A conversation with mayoral candidate, Commissioner George Cardenas.
2026/09/16
In the next installment in our series interviewing mayoral candidates, our panel sits with George Cardenas to learn his plan for Chicago.
Settlements, retirements, anniversaries.
2026/09/12
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 discuss.
Comptroller Susana Mendoza, candidate for mayor of Chicago.
2026/09/09
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.
White Sox relocating, Brandon's budget deficit, another mass shooting.
2026/09/06
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.
Custer drops from the BOE race, the mayor's budget "solution," and another divorce record is unsealed.
2026/08/30
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.
A conversation with mayoral candidate, John Kelly.
2026/08/27
Today, our host interviews John Kelly, lobbyist and candidate for mayor of Chicago.
CTU sues over a cartoon, tollway costs rise, the Chicago City Council's porn addict
2026/08/22
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 divorce records. The documents show his ex-wife leveled some pretty pervy charges. Should the bombastic alderman resign? We'll discuss.
CTA's new pilot program, Bears crawl closer to Indiana, SEIU enters BOE race.
2026/08/15
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 elections?
Giannoulias enters mayoral race, PPP fraud, CTU's sustainable community school model is a failure.
2026/08/08
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.

Podcast reviews

Read Chicago Contrarian, The Podcast podcast reviews


4.2 out of 5
14 reviews
★★★★★
Southsidewhitesoxfan 2026/10/03
Informational
Informational podcast
★★★★★
arevieweryoudon'tknow 2026/09/27
Cuts out all the noise
These guys give all of the current Chicago issues a comprehensive review without the establishment spin you always get on local news media. It keeps m...
★★★★★
NRF The Landlord 2026/05/10
Informative
Great listen
check all reviews on apple podcasts

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