The Chicago Way

The Chicago Way w/John Kass (03/09/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, David Gerlach -president of Lincoln College in central Illinois- joins the conversation with an offer for Chicago Mayor Lori Lightfoot to take any of the President Abraham Lincoln statues the […]

The Chicago Way w/John Kass (03/02/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, Chicago Tribune federal courts reporter Jason Meisner goes on a deep dive into where a federal corruption probe into Chicago politicians starts, how it seemingly snared Illinois’ most powerful politician, […]

The Chicago Way w/John Kass (02/25/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, New York Correspondent for The Federalist and contributor to the NY Post, NRO, City Journal -David Marcus looks at how liberal idealism has lost its historical, center-left hold in major […]

The Chicago Way w/John Kass (02/10/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson discusses the logic and calculations behind Democrats’ push to impeach former President Donald Trump. […]

The Chicago Way w/John Kass (02/03/2021): During the COVID-19 pandemic, John Kass and Jeff Carlin continue to podcast socially distanced from secure locations. This week, Hall of Fame NFL writer for the Atlantic and radio host, Dan Pompei joins the podcast to talk about his history with Kasso -including starting out together at The Red, […]

The Chicago Way w/John Kass (01/24/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. Former Chicago Police Superintendent Eddie Johnson talks about ‘moral mistake’ that lead to the early end of his career as Chicago cop, allegations he sexually assaulted a subordinate, the spike in crime, […]

The Chicago Way w/John Kass (01/21/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, RealClear Politics’ Tom Bevan is here with an assessment of how the media covered Donald Trump’s departure from the White House & Joe Biden’s Inauguration, and what the next four […]

The Chicago Way w/John Kass (01/12/2020): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson analyzes this unique moment in U.S. history and how the Republic move forward. Follow […]

The Chicago Way w/John Kass (01/01/21): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, John and Jeff look back at a tough year for local politicians and when politicians aren’t having a good year, everyone suffers. Follow @John_Kass Follow @JPCarlinDownload this episode here by using ‘Save […]

The Chicago Way w/John Kass (12/21/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, John reads his annual Christmas column and the future of how we cover politics is examined. Follow @John_Kass Follow @JPCarlinDownload this episode here by using ‘Save As’ hereSubscribe to The Chicago Way

The Chicago Way w/John Kass (08/13/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, former CEO of the Chicago Public Schools (1995-2001), Paul Vallas looks at how the Chicago Teacher’s Union (CTU) is responding to the CPS’ plan for re-starting in-class learning in January. Plus, Kasso […]

The Chicago Way w/John Kass (12/05/2020): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson looks at U.S. Attorney General William Barr announcing this week a pre-election elevation of […]

The Chicago Way w/John Kass (11/21/2020): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, Chicago Tribune federal courts reporter Jason Meisner joins the show to unwinds the twisted web of federal indictments in the ComEd bribery investigation and how the Iron Triangle of the Chicago Way […]

The Chicago Way w/John Kass (11/14/2020): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, former Chicago Tribune editorial board editor John McCormick logs on to talk about the importance of balanced editing, open conversations in newsrooms, and where journalism needs to be fixed. Follow @John_Kass Follow […]

The Chicago Way w/John Kass (11/06/2020): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, the host of The Crisis Cast and the Communicator in Chief of Serafin & Associates, Thom Serafin analyzes the scandal-plagued Illinois House Speaker Mike Madigan’s impact on Democrat races in Illinois. Then, […]

The Chicago Way w/John Kass (11/02/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. After a hiatus to deal with COVID-19 & to get married, John & Jeff preview the historic election of 2020 and what happens after the dust settles. Follow @John_Kass Follow @JPCarlin Download this episode […]

The Chicago Way w/John Kass (10/13/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, U.S. Supreme Court nominee Judge Amy Coney Barrett’s first-year law professor and former U.S. Ambassador to Malta, Douglas Kmiec — appointed by former President Barack Obama — joins the show to talk […]

The Chicago Way w/John Kass (10/02/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, RealClear Politics’ Tom Bevan looks at the undue criticism of Chris Wallace’s role as moderator of the presidential debate in Cleveland. Plus, professor emeritus of political science at the University […]

The Chicago Way w/John Kass (09/23/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, Kasso tells the tale of a chance encounter with Illinois House Speaker Mike Madigan while out for a ‘socially distanced’ dinner. Then, Chicago Tribune reporter Jason Meisner breaks down a […]

The Chicago Way w/John Kass (09/14/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, John Kass gets a captive audience with US Attorney General William Barr to talk about mail-in voting for the November election, the ‘what ifs’ about President Trump not leaving office, […]

The Chicago Way w/John Kass (08/31/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, RealClear Politics’ Tom Bevan looks at the unusal nature of this year’s DNC/RNC, where the polls stand on President Trump v. Joe Biden (and maybe Michelle Obama?,) and what the pitfalls of […]

The Chicago Way w/John Kass (08/21/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, Kasso presents a fairytale playing out on the streets of Democratically controlled cities across America. Professor emeritus of political science at the University of Chicago, Dr. Charles Lipson also joins the conversation […]

The Chicago Way w/John Kass (08/13/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, former CEO of the Chicago Public Schools (1995-2001) & candidate for mayor, Paul Vallas joins John & Jeff to discuss why he doesn’t think Mayor Lori Lightfoot “knows what she’s doing” when […]

The Chicago Way w/John Kass (08/07/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week John Kass talks about the outpouring of support he’s received in response to grief brought forth by the “cancel culture” attempting to silence him. And Jeff Carlin embraces the grief of losing […]

The Chicago Way w/John Kass (07/22/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. The Communicator in Chief of Serafin & Associates, Thom Serafin joins the podcast to talk about the legal troubles that may or may not lie ahead for Illinois House Speaker Michael Madigan in light […]

The Chicago Way w/John Kass (07/10/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, RealClear Politics’ Tom Bevan is here with his unique analysis of bias in media coverage of President Trump’s 4th of July address, violence plaguing Democratic cities, and how this bias damages national […]

The Chicago Way w/John Kass (07/01/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, prominent conservative radio talk show host Larry Elder talks about his powerful new film, Uncle Tom: An Oral History of the American Black Conservative. Plus, Kasso looks at how we celebrate the […]

The Chicago Way w/John Kass (06/29/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week John Kass and Jeff Carlin discuss the ‘cat’-astrophy that lead to a delay in last week’s Chicago Way. Then, NY Post columnist Karol Markowicz ‘Zooms’ in from New York to talk about […]

The Chicago Way w/John Kass (06/08/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week John Kass and Jeff Carlin are joined by Chicago Alderman Ray Lopez (15th) to discuss his contentious relationship with Chicago Mayor Lori Lightfoot, why not everyone in the community is on board […]

The Chicago Way w/John Kass (06/08/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week John Kass and Jeff Carlin are joined by John Catanzara Jr., the newly elected President of Chicago’s Fraternal Order of Police, for a discussion about calls for defunding the police, removing resource […]

The Chicago Way w/John Kass (06/02/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week John Kass and Jeff Carlin react to the violent looting plaguing Chicago & other American cities after the brutal death of George Floyd. Plus, professor emeritus of political science at the University […]

The Chicago Way w/John Kass (05/25/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, former CEO of the Chicago Public Schools (1995-2001) Paul Vallas joins the conversation via video chat to talk about the urgent need for a COVID-sensitive plan to get kids back to the […]

The Chicago Way w/John Kass (05/19/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, editorial cartoonist Scott Stantis dials up a Zoom meeting from his home in Alabama to talk about the COVID-19 pandemic response there and what the post-pandemic world might look like. Plus, Kasso […]

The Chicago Way w/John Kass (05/07/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, RealClear Politics’ Tom Bevan is here to discuss the irony of the New York Times’ “1619 Project” winning a 2020 Pulitzer Prize, why the Michael Flynn scandal isn’t getting more coverage, and […]

The Chicago Way w/John Kass (04/22/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, John Kass connects via Zoom with respected financial analyst Ted Dabrowski, of Wirepoints.org, to discuss how & why bankruptcy might be the only option to fix Illinois’ debt problem. Follow @John_Kass Follow […]

The Chicago Way w/John Kass (04/22/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, John laments being stuck at home without a place to roast a lamb for Easter and what it means to embrace risk in a time of crisis. Plus, the Chicago Way-Back Machine […]

The Chicago Way w/John Kass (04/09/20): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast from secure locations. This week, John looks at how people deal with being isolated during high holidays and why politics never closes during a crisis. Plus, Jeff Carlin presents an interview with the Chicago Tribune’s Gary Marx […]

The Chicago Way w/John Kass (04/03/20): John Kass & Jeff Carlin persevere during these trying times to bring you a new episode of the Chicago Way. On this episode, John looks at the icons we turn to in times of crisis. John also offers up an invention for keeping people from touching their faces and […]

The Chicago Way w/John Kass(03/25/20): John Kass & Jeff Carlin are back in your ears amid the COVID-19 pandemic to discuss what’s going on their lives and families. Plus, we take you back to one of the earliest podcasts on the Chicago Way with our friend Scott Stantis and the drivers of the Wienermobile. Follow […]

The Chicago Way w/John Kass(03/08/20): This week John Kass and Jeff Carlin are joined by Dr. Charles Lipson, professor emeritus of political science at the University of Chicago, to discuss the dangers of diminished institutions in light of Sen. Chuck Schumer’s recent threats toward Supreme Court Justices Neil Gorsuch & Brett Kavanaugh. Then, Republican candidate […]

The Chicago Way w/John Kass(03/02/20): This week John Kass and Jeff Carlin are joined by Democrat candidate for Cook County State’s Attorney Bill Conway to discuss why he’s the lawyer ready to take on Kim Foxx in the March 17th, Illinois primary. And, there’s more to the story about why we celebrate Christopher Columbus Day. […]

The Chicago Way w/John Kass(02/25/20): This week John Kass and Jeff Carlin are joined by attorney Patrick Collins (King & Spalding), who led the legal team that successfully prosecuted ex-governor George Ryan for racketeering, to look at Rod Blagojevich’s claims about his unfair prosecution. Plus, the Chicago Tribune’s Gary Marx stops by to fill in […]

The Chicago Way w/John Kass(02/18/20): This week John Kass and Jeff Carlin are joined by Co-Founder & President of RealClearPolitics, Tom Bevan to diagnose the problems facing the Democratic party as they head into primaries in Nevada, South Carolina, and eventually ‘Super Tuesday.’ Will Joe Biden pack up and go home? Did Amy Klobuchar steal […]

The Chicago Way w/John Kass (02/11/20): This week John Kass and Jeff Carlin are joined by David Harsanyi, senior writer for National Review and the author of First Freedom: A Ride through America’s Enduring History with the Gun, to talk about how so-called ‘fact-checkers’ impact the reality of politics and journalism. Plus, Kasso offers up […]

The Chicago Way w/John Kass (02/03/20): This week John Kass and Jeff Carlin talk with director Michael Pack about his new documentary ‘Created Equal: Clarence Thomas in His Own Words,’ wherein Pack spent over 30 hours interviewing Justice Thomas to better understand his humble beginnings and his strident path to becoming a Supreme Court Justice. […]

The Chicago Way w/John Kass (01/28/20): This week John Kass and Jeff Carlin are joined by Democratic candidate for Cook County State’s Attorney Donna More to talk about how she plans to beat perennial candidate Bob Fioretti, incumbent friend-to-the-stars Kim Foxx, and Bill Conway’s father’s checkbook. Plus, Kasso offers up a lesson on journalistic ethics […]

The Chicago Way w/John Kass (01/21/20): This week John Kass and Jeff Carlin are joined by adjunct professor of crisis communications in Northwestern University’s Medill, Hud Englehart, to look at how professionals and politicians handle crises like federal scrutiny or Uncle RICO circling the block in his bus. Plus, retired state appellate Judge Sheila O’Brien […]

The Chicago Way w/John Kass (01/15/20): This week John Kass and Jeff Carlin are joined by Chicago Tribune reporter Jason Meisner to talk about the infamous email from longtime Springfield power broker Mike McClain that is reverberating through Springfield, the ever-expanding federal probe into Illinois politics, and why Mike Madigan’s name always seems to enter […]

The Chicago Way: Ep. 227(1/8/20): John Kass and Jeff Carlin are joined by Dr. Charles Lipson, professor emeritus of political science at the University of Chicago, to discuss the complexities of a possible war with Iran and how this might impact the 2020 election. Follow @John_Kass Follow @charles_lipson Follow @JPCarlin Download this episode here by […]

The Chicago Way: Ep. 226 (12/18/19): John Kass and Jeff Carlin are joined by Wall Street Journal columnist and bestselling author Kim Strassel to talk about the “Resistance” has worked to derail President Trump and democracy in Washington, D.C. Follow @John_Kass Follow @KimStrassel Follow @JPCarlinr Download this episode here by using ‘Save As’here

The Chicago Way: Ep. 225(12/10/19): John Kass and Jeff Carlin are joined by Chicago Tribune political reporter Ray Long with an update on the FBI’s look into the political dealings of Illinois’ powerful Speaker of House Mike Madigan. Then, Tribune police reporter Jeremy Gorner stops by to take a deep dive into the saga of […]

The Chicago Way: Ep. 224(12/03/19): John Kass and Jeff Carlin are joined by Robert Grant, former special agent in charge of the Chicago FBI, with the second part of their conversation about Chicago’s rich history of FBI activity targeting organized crime, politicians behaving badly, and an international terrorist organization responsible for the Mumbai massacre of […]

The Chicago Way: Ep. 222(11/26/19): John Kass and Jeff Carlin are joined by Robert Grant, former special agent in charge of the Chicago FBI, with a candid discussion on the bureau’s rich history of bringing down organized crime and politicians stealing tax dollars. Plus, how do national headlines and the forthcoming Justice Department Inspector General […]

The Chicago Way: Ep. 222(11/20/19): John Kass and Jeff Carlin are joined by Dr. Charles Lipson, professor emeritus of political science at the University of Chicago, to discuss the ongoing impeachment inquiry, how ‘cancel culture’ is seeping into everyday life, and the legacy of President Truman. Plus, Chicago Tribune’s Ray Long ties together the ever-growing […]

The Chicago Way: Ep. 221 (11/11/19): John Kass and Jeff Carlin are joined by Rafael Mangual, criminal justice policy analyst for the conservative Manhattan Institute and contributing editor to City Journal, to discuss the challenges the country faces when ‘social justice warriors’ bring their agendas to offices of State’s Attorneys. Plus, Chicago Tribune columnist and […]

The Chicago Way: Ep. 220 (11/01/19): John Kass and Jeff Carlin are joined by the Chicago Tribune reporter covering the Dirksen U.S. Courthouse Jason Meisner with another incredible update about numerous ongoing federal investigations into Illinois’ political hijinx. This week, it’s state Rep. Luis Arroyo being brought up federal bribery charges after he was allegedly […]

The Chicago Way: Ep. 219 (10/25/19): John Kass and Jeff Carlin are joined by former mayoral candidate & former CEO of Chicago Public Schools, Paul Vallas with his thoughts on how to make tax dollars go further in Mayor Lori Lightfoot’s budget and the negotiations between the Chicago Teachers Union & Chicago Public Schools. Then, […]

The Chicago Way: Ep. 218 (10/18/19): John Kass and Jeff Carlin are joined by former Cook County GOP chair Chris Robling to look at the Democrat’s(with the help of Beltway media & CNN’s Jeff Zucker) impeachment agenda, the scattered field of 2020 candidates, and Chicago Way politics at play on a national level. Plus, Kasso […]

The Chicago Way: Ep. 217 (10/15/19: John Kass and Jeff Carlin are joined by financial analyst & President of Wirepoints.org Ted Dabrowski to look at the real numbers behind contract negotiations between the Chicago Teachers Union and Chicago Mayor Lori Lightfoot’s administration. Follow @John_Kass Follow @ilpoliski Follow @jpcarlin Download this episode here by using ‘Save […]

The Chicago Way w/John Kass – Ep 216(10/11/19): This week, John Kass and Jeff Carlin are joined by the Chicago Tribune reporter covering the Dirksen U.S. Courthouse, Jason Meisner with an update on multiple federal investigations that all have the hallmarks of Hollywood mob film. Follow @John_Kass Follow @jmetr22b Follow @JPCarlin Download this episode here […]

The Chicago Way w/John Kass – Ep 215(10/04/19): This week, John Kass and Jeff Carlin are joined by legendary author George R.R. Martin to talk about the success of “Game of Thrones” getting in the way of finishing the “A Song of Ice and Fire” series and how his dreams are haunted by the characters […]

The Chicago Way w/John Kass – Ep 214 (09/30/19): This week, John Kass and Jeff Carlin sit down with Dr. Charles Lipson, professor emeritus of political science at the University of Chicago, to discuss how politics has overtaken every aspect of modern life and what lead us to this place. Follow @John_Kass Follow @Charles_Lipson Follow […]

The Chicago Way w/John Kass – Ep 213(09/27/19): This week, John Kass and Jeff Carlin are joined by billionaire Morningstar founder & new owner of the Chicago Fire Soccer Club, Joe Mansueto. In a wide-ranging discussion, Mansueto talks about falling in love with soccer watching his kids play, the team’s infamous name, how he hopes […]

The Chicago Way w/John Kass – Ep 212 (09/19/19):This week, John Kass and Jeff Carlin are joined by Chicago Tribune’s Kristen McQueary to discuss why cities like Peoria and other small municipalities will have to feel the crush of Illinois’ mountain of financial debt before any meaningful reform will take place and the politics of […]

The Chicago Way w/John Kass (09/16/19): This week John Kass and Jeff Carlin are joined by the co-founder of Real Clear Politics Tom Bevan to look at where the field of Democrats stand following the latest debate and offer some advice on using satire to make a point. Follow @John_Kass Follow @TomBevanRCP a class=”twitter-follow-button” href=”https://twitter.com/jpcarlin>Follow […]

The Chicago Way: Ep. 210(09/06/19): John Kass and Jeff Carlin are joined by financial analyst & President of Wirepoints.org Ted Dabrowski to look at the overwhelming financial debts facing Chicago and the options Mayor Lori Lightfoot has before her, including bankruptcy. And, Finance Committee Chairman Ald. Scott Waguespack breaks down what he’s discovered while trying […]

The Chicago Way: Ep. 209 (08/29/19): John Kass and Jeff Carlin are joined by retired Judge Sheila O’Brien to talk about the appointment of former U.S. Attorney Dan Webb as a Special Prosecutor in the investigation into Cook County State’s Attorney Kim Foxx’s handling of the Jussie Smollett case. Also up for discussion, what happens […]

The Chicago Way w/John Kass – Ep 208: John Kass and Jeff Carlin are joined by former federal prosecutor & senior fellow at the National Review Institute Andrew C. McCarthy to discuss his new book “Ball of Collusion: The Plot to Rig an Election and Destroy a Presidency.” Plus, WGN-TV’s Ben Bradley breaks down his reporting […]

The Chicago Way w/John Kass – Ep 207: John Kass and Jeff Carlin are joined by the co-founder of Real Clear Politics, Tom Bevan. On the docket this week, why a consortium of Chicago Teacher’s Union members went on an educational trip to visit the socialist nation of Venezuela, how the silence among the media […]

The Chicago Way w/John Kass – Ep 206: John Kass and Jeff Carlin sit down with Dr. Charles Lipson, professor emeritus of political science at the University of Chicago, about how emotion & culture are used to steer political discussions and ultimately agendas that are devoid of logic & reason. Specifically up for discussion, a […]

The Chicago Way, Ep. 205: This week John Kass and Jeff Carlin are joined by senior editor at The Federalist and Fox News contributor Mollie Hemingway to talk about her new book “Justice on Trial: The Kavanaugh Confirmation and the Future of the Supreme Court” that she co-authored with chief counsel and policy director of […]

The Chicago Way, Ep. 204: This week John Kass and Jeff Carlin are joined by conservative activist and morning talk show host on WIND-AM 560 Dan Proft to discuss the “sentimental barbarism” on display during the second round of Democratic debates. Then, Chicago Tribune reporter Jason Meisner tries to untangle the wide-reaching web of federal […]

The Chicago Way, Ep. 203: This week John Kass and Jeff Carlin are joined by WBEZ investigative reporter Dan Mihalopoulos to talk about Chicago Ald. Carrie Austin’s family tree and the almost $700k in tax-payer supported salaries that she and her various family members receive. Then, Pat Brady of Next Generation Strategies talks about the […]

The Chicago Way w/John Kass – Ep 202: John Kass and Jeff Carlin are joined by retired Judge Sheila O’Brien to talk about her latest filings in her quest for getting a special prosecutor to look at the Jussie Smollett case and why she thinks it’s time for Chicago’s big law firms to ‘step up’ […]

The Chicago Way w/John Kass – Ep 201: John Kass and Jeff Carlin are joined by Chicago Tribune columnist and editorial board member Kristen McQueary to talk about legal ripples in Illinois House Speaker Michael Madigan and news that former gubernatorial candidate Jeanne Ives plans on challenging Rep. Sean Casten for his Congressional seat. Plus, […]

The Chicago Way w/John Kass – Ep 200: John Kass and Jeff Carlin are joined the Chicago Tribune’s Jason Meisner to talk about how while he was on vacation, he got the scoop on R. Kelly’s federal case. The co-host of ‘Sound Opinions’ and author of “Soulless: The Case Against R. Kelly,” Jim DeRogatis dive […]

The Chicago Way w/John Kass – LIVE: John Kass and Jeff Carlin take over “Extension 720” on 720 WGN to talk about the intersection of politics & culture with political scientist and University of Chicago professor emeritus Charles Lipson, the secrets of great BBQ with the “Yoda to Kasso’s Jedi-grilling” and author of “Low & […]

The Chicago Way w/John Kass – Ep 199: John Kass and Jeff Carlin are joined by the lawyers representing Harvey Weinstein, Donna Rotunno & Damon Cheronis, to discuss if the deluge of media coverage surrounding their high-profile client will hamper their ability to get a fair trial. And, Tom Ringhausen of Ringhausen Orchard & Market […]

The Chicago Way w/John Kass – Ep 198: John Kass and Jeff Carlin are joined by the co-founder and publisher of Real Clear Politics Tom Bevan to analyze the ever-growing cast of hopefuls vying for the DNC 2020 nomination. Plus, Kasso offers an updated version of the United States’ founding document, one that better reflects […]

The Chicago Way w/John Kass – Ep 197: John Kass and Jeff Carlin are joined by renowned election lawyer Burt Odelson to talk about the Supreme Court’s decision not to rule on the legality of gerrymandering and why former U.S. Attorney Patrick Fitzgerald would be a great pick for special prosecutor in the Jussie Smollett/Kim […]

The Chicago Way w/John Kass – Ep 196: John Kass and Jeff Carlin are joined by retired state appellate Judge Sheila O’Brien to discuss her motivations behind petitioning the court to appoint a special prosecutor to look at Cook County State’s Attorney Kim Foxx’s handling of the Jussie Smollett case. Judge O’Brien also discusses the […]

The Chicago Way w/John Kass – Ep 195: John Kass and Jeff Carlin are joined by Dr. Willie Wilson to talk about why he’s started the WWProgressive PAC and his eagerness to help Mayor Lori Lightfoot; if only she’d call. Then, Veteran Chicago Tribune reporter covering Springfield Ray Long explains how Gov. Pritzker & friends […]

The Chicago Way w/John Kass – Ep 194: John Kass and Jeff Carlin sit down with Dr. Charles Lipson, professor emeritus of political science at the University of Chicago, to talk about the danger facing the republic if the truth why senior officials within the Obama era DoJ, FBI, and CIA initially investigated President Trump’s […]

The Chicago Way w/John Kass – Ep 193: John Kass and Jeff Carlin sit down with the President of Wirepoints, Ted Dabrowski, to talk about what he calls a $40 billion ‘sham’ excuse for a ‘balanced’ budget and how the Illinois General Assembly Democratic leadership of House Speaker Mike Madigan & Senate President John Cullerton […]

The Chicago Way, Kass on the Streets – Ep 192: This week, John Kass is outside the federal courthouse in downtown Chicago we’re longtime alderman Ed Burke pleads not guilty to federal racketeering charges pondering the state of the Chicago Way in the era of Mayor Lori Lightfoot. Kass runs into NBC5’s Carol Marin and […]

The Chicago Way w/John Kass – Ep 191(05/31/19): This week, John Kass and Jeff Carlin are joined by Chicago Mayor Lori Lightfoot to talk about Ald. Ed Burke’s legacy, how Chicago can step out from behind the ominous shadow of the old Chicago Way, and her plan to make Chicago work for its citizens. Plus, […]

The Chicago Way w/John Kass – Ep 190(05/27/19): This week, John Kass and Jeff Carlin are joined by Chicago Tribune’s Kristen McQueary to discuss her newfound knack for home improvement, the state of Gov. JB Pritzker’s legislative agenda as the spring session comes to a close (including an investigation into state Sen. Patricia Van Pelt […]

The Chicago Way w/John Kass – Ep 189(05/23/19): This week, John Kass and Jeff Carlin are joined by the Three-Eyed Raven of the Chicago Tribune newsroom Will Lee to talk about the series finale of ‘Game of Thrones’ and how culture will fill the hole left in people’s hearts. Also, John & Jeff discuss Chicago […]

The Chicago Way w/John Kass – Ep 188 (05/20/19): This week, John Kass and Jeff Carlin are joined by Progressive Caucus chairman Ald. Scott Waguespack(32nd) & newly appointed chairman of the powerful Finance Committee about how the future of Chicago under Lori Lightfoot and to rate Rahm Emanuel’s two-terms as mayor. Also joining the show […]

The Chicago Way w/John Kass – Ep 187 (05/13/19): This week, John Kass and Jeff Carlin are joined by WGN-TV’s Ben Bradley to talk about his conversation with the widow of Chicago Police Officers Eduardo Marmolejo and how media covers tough stories. Plus, Chicago Tribune reporter/Three-Eyed-Rave Will Lee looks at what happens to the void […]

The Chicago Way, Kass on the Street(05/10/19): John Kass looks at how politicians become jesters when the establishment faces upheaval. Kasso also has advice on why Mother’s Day brunches are a bad idea and his new organization, Moms Against Mother’s Day Brunch Society (MAMS). Plus, a chance encounter with Mayor-elect Lori Lightfoot before she is […]

The Chicago Way, Kass on the Street(05/03/19): John Kass & Jeff Carlin take a trip to Chicago Blackhawks Chairman Rocky Wirtz’ office to discuss Chicago Mayor Rahm Emanuel’s reaction to a transition memo Wirtz sent to Mayor-elect Lori Lightfoot. Plus, the ‘Three-eyed Raven’ of the Chicago Tribune newsroom, Will Lee breaks down “The Battle of […]

The Chicago Way w/John Kass(04/30/19): This week John Kass & Jeff Carlin are joined by the Chicago Tribune’s Gregory Pratt to talk about his reporting on the Ald. Ed Burke-Toni Preckwinkle connection. Award-winning editorial cartoonist Scott Stantis stops by to talk about Illinois Gov. JB Pritzker’s tax plan and the push to legalize sports betting […]

The Chicago Way (04/25/19): John Kass catches up with community organizer turned mayoral candidate Ja’Mal Green to talks about how Chicago Mayor-elect Lori Lightfoot should deal with teens amassing downtown and the crime that plagues the hear of Chicago’s tourism areas in the warm summer months. Green also discusses Kim Foxx’s handling of the Jussie […]

The Chicago Way w/John Kass(04/23/19): This week John Kass & Jeff Carlin are joined by Dr. Charles Lipson, professor emeritus of political science at the University of Chicago, to talk about how the media is dealing with the end of the Mueller investigation(without any charges against Donald Trump) and what happens now that the fantasy […]

The Chicago Way (04/18/19): John Kass reports from the courthouse where John “Quarters” Boyle learned his fate after being charged for leaving the scene of an accident two years ago and Illinois Comptroller Susana Mendoza championed upgraded charges against Boyle. Kass also reflects on the storied history of Paris’ Notre Dame Cathedral, Kim Foxx’s “bless”-ing, […]

The Chicago Way w/John Kass (04/12/19): This week John Kass and Jeff Carlin are joined the co-founder & publisher of Real Clear Politics, Tom Bevan, to talk about the credibility issues facing mainstream media in the modern world, specifically media reaction to U.S. Attorney General William Barr telling members of Congress that he has serious […]

The Chicago Way w/John Kass (04/05/19): This week John Kass and Jeff Carlin are joined by Chicago Police Superintendent Eddie Johnson to talk about the changing of the guard at city hall, how the CPD is preparing for the plague of violence brought on warmer Summer temperatures, and Jussie Smollett debacle. Plus, Kasso & Mr. […]

The Chicago Way w/John Kass (04/03/19):On the morning after Lori Lightfoot pulled off a historic, landslide victory over Cook County Board President Toni Preckwinkle in the runoff election for Chicago mayor, John Kass & Jeff Carlin are joined by Chicago Tribune Editorial Board member Kristen McQueary to break down Chicago’s various aldermanic runoff races, the […]

The Chicago Way w/John Kass (04/01/19): This week John Kass and Jeff Carlin are joined by Chicago Tribune Editorial Board member/cartoonist Scott Stantis to talk about how Cook County State’s Attorney Kim Foxx can keep her job. Wirepoints President Ted Dabrowski looks at the massive financial crisis facing the next Mayor of Chicago. Plus, Kasso […]