Chicago Way w/John Kass (02/05/24): On episode 426, Senior Technical Producer & life-long southside resident of Chicago Brian Althimer joins John Kass & Jeff Carlin to share his perspective as someone who was born Englewood and has seen how crime & disinvestment have changed the South Side of the city over his lifetime. Plus, Kasso […]

Chicago Way w/John Kass (01/29/24): This week, Amber Duke (Athey) joins John Kass & Jeff Carlin to discuss her new book, ‘The Snowflakes’ Revolt: How Woke Millennials Hijacked American Media.’ Amber also talks about being cancelled at WMAL and how newsrooms across the country have lost their credibility after allowing ‘Snowflakes’ to press their ill-conceived […]

Chicago Way w/John Kass (01/22/24): RealClear Politics’ Tom Bevan breaks down what Florida Governor Ron DeSantis’s campaign got foolishly wrong, how the GOP ’24 primary is really a Vice Presidential primary, why Nikki Hailey will never be Donald Trump’s VP pick (but Elise Stefanik or Tim Scott will be), and what happens when liberals realize […]

Chicago Way w/John Kass (01/15/24): This week, hometown reporter Anita Padilla talks about her time covering Chicago and what is next as she embarks on a new role as News Director for Florida’s Voice. Plus, John Kass & Jeff Carlin wonder if Mayor Brandon Johnson is cracking from the pressure of membership in Chicago’s clown-carpool […]

Chicago Way w/John Kass (01/01/24): To close out 2023, friend of the show Charles Lipson (the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago) joins John Kass & Jeff Carlin to discuss Charles’ piece in RealClearPolitics about Chicago Mayor Brandon Johnson’s ‘Hat Trick of Dreadful Policies’ and what that means […]

Chicago Way w/John Kass (12/25/23): John Kass & Jeff Carlin discuss former Chicago Way power broker Ed Burke being found guilty of corruption after serving more than 45 years on the City Council and what that means for the verdict in the future of the Chicago Way. Plus, Kasso wonders who has earned the Moutza […]

Chicago Way w/John Kass (12/18/23): On this edition, the host of the Counterculture podcast and conservative political advocate Dan Proft joins John Kass & Jeff Carlin to discuss Dan’s first crack at writing a column for John. Kasso also wonders if Dan is up for tackling the ‘Sentimental Barbarian’ and coming around to loving soccer. […]

Chicago Way w/John Kass (12/11/23): Joining John Kass & Jeff Carlin this week is John’s younger brother Nicholas Kass, a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on matters pertaining to the Eastern Mediterranean, to discuss why thoughtful foreign policy leadership is so important and how […]

Chicago Way w/John Kass (12/04/23): Steve Huntley, columnist, distinguished veteran Chicago editor and newspaperman (and now frequent contributor to johnkassnews.com) is our guest on this edition. John Kass & Jeff Carlin get a preview of Steve’s latest on the crisis in Israel & Gaza. Plus, Kasso wonders if Chicago Mayor Brandon Johnson blaming conservatives for […]

Chicago Way w/John Kass (11/28/23): This week, John Kass & Jeff are joined by Rafael Mangual, the Nick Ohnell Fellow and head of research for the Policing and Public Safety Initiative at the Manhattan Institute and a contributing editor of City Journal, to discuss what Kim Foxx, Tim Edwards, George Soros, and their ilk get […]

Chicago Way w/John Kass (11/15/23): This week we’re behind the scenes as John Kass & Jeff Carlin are on the road this week for a photoshoot. Kasso is launching some merch soon for JohnKassNews.com and former neighbor & veteran photographer, Bill Melonides of MVP Studio Photography is the man for the job (he’s also written […]

Chicago Way w/John Kass (11/06/23): No guest this week as John Kass & Jeff Carlin look at the start of former Chicago Alderman Ed Burke’s federal corruption trial, a historic moment in Chicago politics. Plus, an update from the Rauschenbergers as we learn of Emilee making it to Cairo as she finally made it out […]

Chicago Way w/John Kass (11/01/23): This week, John Kass & Jeff Carlin meet Elgin-native John Rauschenberger to learn about his daughter Emilee Rauschenberger’s plight in southern Gaza after the violence of 10/7. During a visit to see sick family, Emilee, her Palestinian-born husband Mohammad, and their five children have been relocated to an area just […]

Chicago Way w/John Kass (10/22/23): On this episode, Ted Dabrowski of Wirepoints.com joins John Kass & Jeff Carlin to discuss his recent visit to a Chicago Police Station at Division & Larrabee to talk with migrants who have been recently bused from the US/Mexico border and forced to live in tents (if they’re lucky) or […]

Chicago Way w/John Kass (10/17/23): This week, John Kass’ younger brother Nicholas Kass, a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on matters pertaining to the Eastern Mediterranean, joins the conversation to discuss the war between Israel and Hamas and the destruction of innocent lives. Nick […]

Chicago Way w/John Kass (10/10/23): On the 411th episode, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson, joins John Kass & Jeff Carlin to with a sober look at the situation leading up to the events unfolding in Israel & what the future might hold for the […]

Chicago Way w/John Kass (10/02/23): This week, John Kass & Jeff Carlin catch up with former Chicago Alderman Roderick Sawyer (6th – parts of Chatham, Englewood, and West Englewood) to better understand why Chicago is a sanctuary city and how the large influx of migrants/immigrants/refugees to city are creating pressure on scarce resources that residents […]

Chicago Way w/John Kass (09/26/23): On this episode, John Kass & Jeff Carlin offer a social media ‘tip-o-the-hat’ to Chicago Teacher’s Union’s Stacy Davis Gates for taking time from her busy schedule spending CTU funds without answering to anyone and engaging in her child’s Catholic school education to offer up a quality takedown of Kass. […]

Chicago Way w/John Kass (09/20/23): On this special episode, John Kass & Jeff Carlin head to Wilmette, IL for an event hosted by Beth Feeley & Ted Dabrowski of the New Trier Neighbors featuring a conversation between Kass and the co-host of WIND 560’s Morning Answer, Dan Proft. Check out more from Kass at JohnKassNews.com […]

Chicago Way w/John Kass (09/11/23): Paul Vallas, former candidate for Chicago Mayor and CEO of Chicago Public Schools, joins John Kass & Jeff Carlin to discuss the hypocrisy of Chicago Teachers Union President Stacy Davis Gates sending her child to a private school, even though she has a history of calling private schools fascist & […]

Chicago Way w/John Kass (09/04/23): To close out the summer with John Kass & Jeff Carlin is John’s younger brother Nicholas Spyridon Kass, a retired American diplomat with over 30-years of experience -focused on Aegean/Eastern Mediterranean issues, checking in from Romania (watch out for bears!) to discuss what the conflict in Ukraine will look like […]

Chicago Way w/John Kass (08/28/23): This week, RealClear Politics’ Tom Bevanjoins John Kass and Jeff Carlin to look at the most impressive performances in thefirst Republican National Committee presidential debate of the 2024 election.Were some of them so weak that they caused irreparable harm to their politicalambitions?And Kasso wonders out loud if Joe Biden keeps […]

Chicago Way w/John Kass (08/21/23): Chicago mother, author and teacher Erin Geary joins John Kass & Jeff Carlin to discuss the state of Chicago’s Public Schools. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by using ‘Save As’ hereSubscribe to The Chicago Way

Chicago Way w/John Kass (08/14/23): This week, John Kass & Jeff Carlin are together to discuss Chicago Mayor Brandon Johnson firing Dr. Alison Arwady late Friday and the fallout from that decision. Plus, Kasso tells the story of a dark stranger who comforted him in a time of need that turned out to be NHL […]

Chicago Way w/John Kass (08/07/23): John Kass & Jeff Carlin are looking for answers and statues after Chicago Mayor Brandon Johnson calls a mob young people looting a convenience store ‘baby Al Capones’ while remaining silent on the fate of three Christopher Columbus statues that were torn down in the dead of night over 3 […]

Chicago Way w/John Kass (07/27/23): Summer break is over, John Kass and Jeff Carlin are back to catch you up on where they’ve been and remember their friend, the late Blackhawks Chairman Rocky Wirtz. Plus, Kasso shares a bear encounter story made for TV. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com […]

Chicago Way w/John Kass (07/13/23): This week, Garry McCarthy -former Chicago Police Superintendent and current Chief of Police for Willow Springs, IL- joins John Kass and Jeff Carlin to discuss the tragic loss of his daughter to a fentanyl overdose last year and why China, Mexico, and Congress share the blame for the over 110,000 […]

Chicago Way w/John Kass (06/30/23): To celebrate Independence Day, Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, is here to tackle the Supreme Court’s latest rulings on affirmative action and why there’s a serious case for impeaching US Attorney General Merrick Garland. Check out more Kasso at JohnKassNews.com […]

Chicago Way w/John Kass (06/23/23): This week, Jason Whitlock, the host of Fearless and longtime sports journalist joins John Kass & Jeff Carlin to discuss his mission to “Reclaim the Rainbow” and pushback on the militant way ‘PRIDE’ is being exhibited in the mainstream media. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – […]

Chicago Way w/John Kass (06/13/23): On this episode, John’s younger brother Nicholas Kass, a retired American diplomat with over 30-years of experience -focused on Aegean/Eastern Mediterranean issues, takes a deep look at how we got to a war of attrition in Ukraine and whether or not this instability puts the future of NATO at risk. […]

Chicago Way w/John Kass (06/09/23): One of our favorite repeat guests, the ‘Cooking Cop’ –Peter V. Bella, talks about working as a crime scene photog and the collection of b&w photos he has on display at the great Tony Fitzpatrick‘s Dime studio space. Peter’s works are on display through June. Check out more Kasso at JohnKassNews.com […]

Chicago Way w/John Kass (05/23/23): From RealClearInvestigations & The Federalist, Mark Hemingway joins John Kass & Jeff Carlin to discuss the ‘damming Durham Report’ and analyze why media outlets are ignoring the report’s findings. Plus, Kasso wonders if the children of the future will even know the damming things the FBI did during the 2016 […]

Chicago Way w/John Kass (05/16/23): John Kass & Jeff Carlin discuss local sports media ‘personalities’ making inane & tasteless remarks about Dan Proft’s dead mother -friend of the show, the dawn of the Brandon Johnson era in Chicago as the new mayor begins his tenure on the 5th floor of City Hall, and the departure […]

Chicago Way w/John Kass (05/08/23): On this edition, the co-host of WIND 560’s Morning Answer and conservative politico Dan Proft joins John Kass & Jeff Carlin to discuss the verdict in the “ComEd Four” case and why naïve jurors make him mad. Plus, is Evanston Township High School bringing back segregation to solve racism? Check […]

Chicago Way w/John Kass (05/03/23): This week, RealClear Politics’ Tom Bevan is here to discuss the forecast for Biden/Harris against Trump, DeSantis, and the rest. Plus, what really went down with the swift cancelation of Tucker Carlson’s top-rated cable show? Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin […]

Chicago Way w/John Kass (04/24/23): Joining the conversation this week is Corey Brooks, Founder and Senior Pastor at New Beginnings Church of Chicago and the Founder and CEO of Project H.O.O.D, to discuss with John Kass & Jeff Carlin the need for parents to be held accountable for the crimes of their children and for […]

Chicago Way w/John Kass (04/12/23): This week, John Kass and Jeff Carlin are joined by the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago Charles Lipson with a look at the national issues facing the body politic, including Manhattan District Attorney Alvin Bragg deciding to indict former President Donald Trump, progressives […]

Chicago Way w/John Kass (04/06/23): On this episode, Chicago Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin in a discussion about the challenges facing mayor-elect Brandon Johnson and how the more progressive landscape on the City Council will deal with these issues. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com […]

Chicago Way w/John Kass (03/27/23): With a week to go in the run-off election to decide Chicago’s next mayor, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin, joins John Kass & Jeff Carlin to size up what endorsements from Senators Dick Durbin & Bernie Sanders mean and where Brandon […]

Chicago Way w/John Kass (03/20/23): This week, former Cook County and federal prosecutor Bob Milan joins John Kass & Jeff Carlin to talk about which strategies and policies the next mayor of Chicago should consider, like holding weekly press conferences to call out elected officials who fail to keep the city safe, like the chief […]

Chicago Way w/John Kass (03/17/23): Fresh off her role as moderator for the mayoral debate between Brandon Johnson and Paul Vallas, NBC5 Chicago’s Mary Ann Ahern joins John Kass & Jeff Carlin to discuss the pitfalls of being a public figure, perceived bias vs. real bias, the big questions facing the candidates before the April […]

Chicago Way w/John Kass (03/08/23): On this episode, former Chicago City Hall reporter and award winning columnist Ray Hanania joins John Kass & Jeff Carlin to discuss how the media landscape in Chicago has changed over the last 30 years and why criminals get bolder while cops lose the proper resources to do their job. […]

Chicago Way w/John Kass (03/01/23): On this edition, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast Thom Serafin joins John Kass and Jeff Carlin to look at where Lori Lightfoot went wrong in her failed bid for re-election and what that means for runoff between Brandon Johnson and Paul Vallas. […]

Chicago Way w/John Kass (02/21/23): Chicago Alderman Brendan Reilly (42nd) joins John Kass & Jeff Carlin to discuss why he isn’t endorsing Lori Lightfoot for re-election, the bad numbers behind the deal Mayor Lightfoot rammed through City Council, and why State’s Attorney Kim Foxx & Chief Judge Tim Evans need to go. Check out more […]

Chicago Way w/John Kass (02/17/23): On episode 382, Illinois Policy Institute Vice President of Marketing Austin Berg joins John Kass & Jeff Carlin to talk about the debut of “Local 1: The Rise of America’s Most Powerful Teachers Union” and explain how mayoral candidate Brandon Johnson seeks to create a socialist paradise in Chicago, starting […]

Chicago Way w/John Kass (02/13/23): Joining the conversation on this edition, the former Inspector General for Chicago, Joe Ferguson, is here to discuss why the media is letting down voters in the race for mayor, some of the pitfalls that have devoured Mayor Lori Lightfoot’s time on the 5th floor of City Hall, and why […]

Chicago Way w/John Kass (02/09/23): In this very special episode, Super Bowl champion & Hall of Fame linebacker Mike Singletary joins John Kass & Jeff Carlin to talk about his foundation –Changing Our Perspective– partnering with Pulse4Pulse to raise awareness about heart health among under-resourced communities. Mike also talks about what it takes to be […]

Chicago Way w/John Kass (02/06/23): With only a few weeks until election day in Chicago, retired CPD sergeant Mike Cummings is here to discuss why the 19th Ward is ready for a change and Mayor Lori Lightfoot, Police Superintendent David Brown, and Alderman Matt O’Shea have to go. Plus, Kasso takes a crack at monologue […]

Chicago Way w/John Kass (1/20/23): On this edition, John Kass takes us behind the scenes of his recent health ordeal, what his recovery has been like at the Shirley Ryan AbilityLab, and his faith has helped carry him through. Plus, veteran political guru at Serafin & Associates and co-host of The Crisis Cast Thom Serafin […]

Chicago Way w/John Kass (1/23/23): Joining John Kass & Jeff Carlin on this edition is former longtime editor of the Chicago Sun Times editorial page and now writing for JohnKassNews.com, Steve Huntley. On the docket, the last weeks of the race for Chicago Mayor is getting interesting as new polling from Fox32 shows incumbent Mayor […]

The Chicago Way w/John Kass (1/18/23): John Kass is back with a message to everyone about what’s been happening. Plus, John’s brother Nicholas Kass joins Jeff Carlin for an update on Kasso’s recovery. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by using ‘Save […]

The Chicago Way w/John Kass (1/6/23): On this episode, the former CEO of the Chicago Public Schools (1995-2001) and candidate hoping to unseat Lori Lightfoot, Paul Vallas joins John Kass & Jeff Carlin to discuss his plans for growing Chicago and tackling crime, education, and fiscal issues facing the city. Plus, Kasso recovers in the […]

The Chicago Way w/John Kass (1/1/2023): John Kass & Jeff Carlin look at the year that was in politics and news. Kass & Carlin also look forward toward 2023 and the politics of the day. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by […]

The Chicago Way w/John Kass (12/21/2022): John Kass & Jeff Carlin celebrate the never-ending gift of interest that is Chicago politics, the city’s ‘You Name a Plow’ contest, and the holiday season. Plus, Kasso & Carlin toast to a merry Christmas. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow […]

The Chicago Way w/John Kass (12/16/2022): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin to discuss her new book, Laptop from Hell: Hunter Biden, Big Tech, and the Dirty Secrets the President Tried to Hide, and outline the wide-ranging efforts to keep this story under wraps (including bad actors inside ‘Big […]

The Chicago Way w/John Kass (12/13/2022): On this edition, John Kass & Jeff Carlin tackle the news of the week including the ongoing expose of the ‘Twitter Files’ -which point to some very unconstitutional practices, terrible news out of suburban Chicago where students filmed themselves laughing & abusing a cohort with Down syndrome at York […]

The Chicago Way w/John Kass (12/09/2022):  This week, RealClear Politics’ Tom Bevan is here to discuss accountability in polling, what is the heck is happening at Francis W. Parker School in Chicago, Donald Trump’s impact on the future of the Republican party, and the Royals on display. Plus, Carlin admits to being part of the problem. […]

The Chicago Way w/John Kass (12/06/2022): On this episode, John Kass and Jeff Carlin analyze the finalized slate of candidates seeking to make Lori Lighfoot a one-term mayor, question why the media is blatantly ignoring news of governmental censorship at Twitter, and asks the question- who plays Barack Obama in the Netflix documentary on how […]

The Chicago Way w/John Kass (12/02/2022): On this edition, Ald. Ray Lopez (15th) discusses dropping his bid for mayor, what that means for the race to unseat Mayor Lori Lightfoot in 2023, and running a race for the redrawn 15th ward. Plus, Kasso wonders if the late legend of WLS radio morning drive Don Wade would […]

The Chicago Way w/John Kass (11/21/2022): On this Thanksgiving edition, John Kass & Jeff Carlin offer up some things to be thankful for like friends, family, the bountiful condition state of Chicago politics, and the World Cup. Plus, Kasso wonders if Twitter were a gas station restroom, would we care about the cockroaches’ feelings? Check […]

The Chicago Way w/John Kass (11/18/2022): This week, Chicago Bears great Gary Fencik joins John Kass & Jeff Carlin to discuss his life & career in Chicago, the time he ran with the bulls, a throwback Illinois Lottery commercial, and his future in politics…or maybe lack thereof. Plus, Kasso wonders if Chicago Mayor Lori ‘Phallus […]

The Chicago Way w/John Kass (11/14/2022): On this episode, John Kass & Jeff Carlin preview the week’s news including the announcement that Rep. Jesus ‘Chuy’ Garcia is seeking to unseat Mayor Lori Lightfoot, Ald. Tom Tunney deciding not too challenge Lori, and the forthcoming big announcement from Donald Trump. Check out more Kasso at JohnKassNews.com Follow […]

The Chicago Way w/John Kass (11/10/2022): On this edition, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins John Kass & Jeff Carlin to unpack the 2022 mid-term elections, look at the future races in Illinois & Chicago, and to offer a cheerful perspective on voter turnout. Plus, Kasso […]

The Chicago Way w/John Kass (11/04/2022): As the clock winds down on the 2022 midterm elections, John Kass and Jeff Carlin look at the hair-on-fire antics of the media, what happens when media and political parties work in concert to alter the voting landscape, and call for everyone to relax. Plus, is Kasso the right […]

The Chicago Way w/John Kass (10/31/2022): John Kass and Jeff Carlin are joined this week by the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago Charles Lipson to discuss how nationwide violence will lead the a ‘red wave’ on election day, what happens when the GOP retakes the House, and […]

The Chicago Way w/John Kass (10/28/2022): In preparation for Halloween, John Kass & Jeff Carlin share their favorite scary (political) stories from their week and offer up considerations for the ‘Golden Moutza’ for October. Plus, who is scarier than a politician on social media? Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com […]

The Chicago Way w/John Kass (10/24/2022): Entering the ‘No Chumbolone Zone’ this week is Ted Dabrowski of Wirepoints.com to discuss new data on how the pandemic impacted student achievement, the misconceptions about the ‘SAFE-T’ Act, and why Amendment 1 on the ballot in Illinois is bad for the state. Plus, Kasso has warning about carnival […]

The Chicago Way w/John Kass (10/21/2022): A fed up former ABC7 Chicago reporter Charles Thomas, who -after almost 30 years retired in broadcasting- has come under fire for taking $50,000 from a conservative super PAC run by Dan Proft to promote Daren Bailey as a better candidate than Governor JB Pritzker, joins John Kass and […]

The Chicago Way w/John Kass (10/17/2022): On this edition, veteran reporter and special contributor to WGN Radio & NewsNation Anna Davlantes joins John Kass & Jeff Carlin to offer a historical perspective on the current state of Chicago’s political, criminal, and legal affairs. Also on the docket, why some in the media refuse to question […]

The Chicago Way w/John Kass (10/11/2022): This week, RealClear Politics’ Tom Bevan checks in to discuss polling and a new RCP project aimed at making ‘bad polls’ easier to recognize. Bevan also takes on the major storylines & key races to watch a month before the 2022 midterm elections. Check out more Kasso at JohnKassNews.com Follow […]

The Chicago Way w/John Kass (10/04/2022): The legend himself, Chicago Bear Ed O’Bradovich from The Hamp & O’B Show, discusses why he thinks the Bears should move to Arlington Heights, explains why he can’t stand the notion of ‘rebuilding year,’ diagnoses what’s wrong with Justin Fields stats, and tells the story of watching an opponent […]

The Chicago Way w/John Kass (09/28/2022): This week, John Kass and Jeff Carlin are joined by the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson, to discuss civic nationalism’s role in society and politics, the media’s coverage of Hurricane Ian, polling that leaves Democrats and Republicans less than […]

The Chicago Way w/John Kass (09/21/2022): This week, St. Senator John Curran (R-Downers Grove) -former assistant Cook County state’s attorney- joins John Kass and Jeff Carlin to debunk the half-truths surrounding the Safe-T Act and offer up a sobering view of what will happen when the law goes into effect beginning Jan. 1, 2023, abolishing […]

The Chicago Way w/John Kass (09/12/2022): On this episode, John Kass & Jeff Carlin are joined by Matt Rosenberg to discuss the work at WirePoint.org and the ‘unraveling’ of Chicago. Plus, Kasso reacts to this news story about a violent mugging in Chicago’s Lakeview neighborhood and wonders if everyone hears screams the same? Check out […]

The Chicago Way w/John Kass (09/07/2022): Joining the conversation with John Kass & Jeff Carlin is Republican candidate for Illinois Attorney General, Tom Devore. Attorney Devore has questions about Gov. JB Pritzker’s abuse of executive orders, current AG Kwame Raoul’s handling of the Jenny Thornley case, and the Illinois General Assembly’s passing of the flawed […]

The Chicago Way w/John Kass (09/03/2022): John Kass & Jeff Carlin discuss the news of the week on this episode including a foreboding primetime address from President Joe Biden, Chicago Mayor Lori Lighfoot’s interesting words for Texas Gov. Greg Abbott, and ‘Ball of Confusion’ that is modern politics. Check out more Kasso at JohnKassNews.com Follow Everything […]

The Chicago Way w/John Kass (08/30/2022): On this edition, the co-host of WIND 560’s Morning Answer and conservative political advocate Dan Proft joins John Kass & Jeff Carlin to discuss Chicago Mayor Lori Lighfoot’s accusing Proft’s People Who Play By the Rules super PAC of darkening her skin tone in ads to scare white people […]

The Chicago Way w/John Kass (08/26/2022): On this episode, John Kass and Jeff Carlin talk with the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson to get his assessment of the FBI raid on Mar-a-Lago, the constitutionality of President Biden’s executive order on student loan debt, and the […]

The Chicago Way w/John Kass (08/16/2022): On this edition, John Kass & Jeff Carlin catch up with Chicago Alderman Roderick Sawyer (6th – parts of Chatham, Englewood, and West Englewood) to discuss his father’s legacy fulfilling late Mayor Harold Washington’s goals and what he hopes to achieve if he is elected to be the next […]

The Chicago Way w/John Kass (08/12/2022): On this edition, John Kass and Jeff Carlin are joined by the 911 dispatcher credited with managing the chaotic situation involving the murder of Chicago police officer Ella French and helping to save the life of officer Carlos Yanez Jr,. Keith Thornton. Keith recently resigned from the job he […]

The Chicago Way w/John Kass (08/09/2022): On this episode, John Kass & Jeff Carlin look at Kass’ time traveling theories, the ‘cheep, cheep’ at the fence, crime strategies in Chicago, and what’s next for Mayor of Chicago. Plus, Kasso prepares for shoulder surgery. (Check out more Kasso at JohnKassNews.com) Follow Everything John Kass – JohnKassNews.com Follow […]

The Chicago Way w/John Kass (08/01/2022): This week, John Kass & Jeff are joined by Rafael Mangual, the Nick Ohnell Fellow and head of research for the Policing and Public Safety Initiative at the Manhattan Institute and a contributing editor of City Journal, to discuss his first book Criminal (In)Justice: What the Push for Decarceration […]

The Chicago Way w/John Kass (07/29/2022): On this episode, John Kass & Jeff Carlin react to a solid week of ‘efforting’ by Chicago Mayor Lori Lighfoot as she announces plans to put a dome on Soldier Field in a bid to keep the Chicago Bears from leaving for the suburbs like so many other Chicagoans. […]

The Chicago Way w/John Kass (07/27/2022): This week, John Kass & Jeff Carlin are joined by former Chief Deputy U.S. Marshal John O’Malley to talk about his time as the City of Chicago’s Deputy Mayor of Public Safety and what it will take to bring Chicago’s violence under control. (Check out more Kasso at JohnKassNews.com) Follow […]

The Chicago Way w/John Kass (07/19/2022): Joining the conversation with John Kass & Jeff Carlin, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson is here to discuss President Joe Biden’s meet & greet with Saudi Crown Prince Mohammed bin Salman, explore growing energy issues, and perform a […]

The Chicago Way w/John Kass (07/13/2022): On this episode, John Kass & Jeff Carlin geek out about the James Webb Space Telescope (nicknamed Webb or JWST) and wonder if Chicago Mayor Lori Lighfoot will be able reign in the violence plaguing her ‘Summer of Joy.’ Pluss, Kasso settles in for recovery from shoulder surgery with […]

The Chicago Way w/John Kass (07/06/2022): On this edition, John Kass & Jeff Carlin are joined by John’s younger brother Nicholas Spyridon Kass, a retired American diplomat with over 30-years of experience -focused on Aegean/Eastern Mediterranean issues, to offer some historical perspective on how republics struggle under strife and what lessons we can learn from […]

The Chicago Way w/John Kass (07/01/2022): Joining John Kass & Jeff Carlin on this edition is veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin to look analyze the results of the 2022 primary election in Illinois and gauge the national ambitions of Gov. JB Pritzker. Check out more Kasso […]

The Chicago Way w/John Kass (06/27/2022): John Kass and Jeff Carlin are joined this week by veteran feature writer, metro reporter, night city editor, metropolitan editor, editorial page editor and a columnist for the opinion pages of the Chicago Sun-Times, Steve Huntley. Steve discusses how the economics and culture of newspapers has changed for the […]

The Chicago Way w/John Kass (06/21/2022): This week, veteran pollster and political operative Rod McCulloch discuss what has played out so far in Republican primary for Illinois governor and pulls back the curtain on political polling. Plus, Kasso’s ‘spidey sense’ is tingling with the prospect of Illinois political combine backing another contender for mayor of […]

The Chicago Way w/John Kass (06/15/2022): Joining John Kass & Jeff Carlin this week is the director of the policing and public safety initiative at the Manhattan Institute, Hannah E. Meyers, to discuss her time with the Intelligence Bureau of the New York City Police Department working on counterterrorism and outline how progressive policies & […]

The Chicago Way w/John Kass (06/06/2022): This week with John Kass & Jeff Carlin, Real Clear Politics’ Tom Bevan talks primaries, polling, and politics. Plus, Kasso wonders what happens when voters are fed up with everything? Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here […]

The Chicago Way w/John Kass (06/01/2022): John Kass & Jeff Carlin are joined by newly-announced candidate for mayor, the former CEO of the Chicago Public Schools (1995-2001), Paul Vallas. Touting his experience in New Orleans after Hurricane Katrina, Paul lays out his plan to fix Chicago’s ‘man-made storms’ of public safety, finances, and education. Check […]

The Chicago Way w/John Kass (05/28/2022): This week, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson joins John Kass & Jeff Carlin to discuss the un-American nature of ‘loyalty oaths,’ why the U.S. needs better leaders, and why no onw is talking about the trial of Hillary […]

The Chicago Way w/John Kass (05/20/2022): This week, John Kass and Jeff Carlin discuss comments of Chicago 911 dispatcher Keith Thornton, Jr. who has seen first hand the surging violence plaguing the city and what happens when the Furies sink the claws into justice system. Check out more Kasso at JohnKassNews.com Follow Everything John Kass – […]

The Chicago Way w/John Kass (05/14/2022): This week, John Kass and Jeff Carlin are joined by the Thomas W. Smith fellow at the Manhattan Institute and author of “The War on Cops,” Heather Mac Donald to discuss the impact of Supreme Court protests, police policing in the modern age, and how Chicago can counter the […]

The Chicago Way w/John Kass (05/08/2022): John Kass and Jeff Carlin look at the week’s news including Supreme Court protests & boneheaded tweets from public officials, and wonder if Chicago Mayor Lori Lightfoot’s touted ‘Summer of Joy’ includes a soundtrack of gunfire… Check out more Kasso at JohnKassNews.com Follow Everything John Kass – JohnKassNews.com Follow @John_Kass […]

The Chicago Way w/John Kass (04/28/2022): John Kass and Jeff Carlin consider the virtue of Chicago Mayor Lori Lighfoot handing out $12million dollars in taxpayer funds in the form of cash cards with the Mayor’s face on them and the start of violence in the city driven by warmer weather. Plus, Jeff sets Kasso straight […]

The Chicago Way w/John Kass (04/25/2022): On this edition, the co-host of WIND 560’s Morning Answer and conservative political advocate Dan Proft joins the conversation to discuss how Illinois’ “donor class” controls elections in the IL and whether-or-not Republican voters will be “tricked” into voting for Richard Irvin in this year’s Republican gubernatorial primary. Plus, […]

The Chicago Way w/John Kass (04/19/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this edition, possible candidate for mayor & former CEO of the Chicago Public Schools (1995-2001), Paul Vallas joins John & Jeff to talk about his concerns about institutional racism in action […]

The Chicago Way w/John Kass (04/15/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, the co-founder & managing editor The Chicago Thinker and a senior at the University of Chicago, Evita Duffy discusses being a conservative on modern college campus and her work at […]

The Chicago Way w/John Kass (04/11/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this edition, Ald. Ray Lopez (15th) discusses his candidacy in the 2023 mayoral race, including how he plans to improve public safety, working with an elected school board, and whether or […]

The Chicago Way w/John Kass (04/09/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this episode, author & director of medical intensive care at Cook County Hospital in Chicago for over 25 years, Dr. Cory Franklin joins the conversation to talk about the crossroads of […]

The Chicago Way w/John Kass (04/06/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. Back from from spending time in the wilderness, John & Jeff offer up candidates for the March edition of ‘Moutza of the Month‘ and discuss Mayor Lori Lighfoot’s day in court. Plus, […]

The Chicago Way w/John Kass (04/01/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. Legendary angler Jac Ford joins John and Jeff to talk about his new book, ‘The View From the Middle Seat: Lessons Learned from a Lifetime of Guiding.’ Plus, Kasso gets Jac to […]

The Chicago Way w/John Kass (03/28/2022): 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 media feedback loop that suppressed the infamous Hunter Biden laptop story, how […]

The Chicago Way w/John Kass (03/25/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, John offers a tribute to March 25th, Greek Independence Day and a history lesson. Plus, John & Jeff take a look at news of the day. Check out more Kasso […]

The Chicago Way w/John Kass (03/21/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. Chicago Sun-Times sports reporter & co-host of The Chicago Soccer Conversation, Brian Sandalow, discusses the culture change inside the Chicago Fire FC’s locker-room and how a winning culture can be contagious. Check […]

The Chicago Way w/John Kass (03/17/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this edition, Illinois State Representative Tim Butler (R-Springfield) discusses a proposed bill that would furnish citizens of Cook County with the ability to recall State’s Attorney Kim Foxx and considers how […]

The Chicago Way w/John Kass (03/15/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. To honor St. Patrick’s Day and the Chicago Outfit’s impact on the Second City, Fox News’ Eric Shawn presents evidence that the notorious Lou Rosanova, high ranking member of the Outfit known […]

The Chicago Way w/John Kass (03/07/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. To close out a big week in Illinois politics, veteran Chicago Tribune political reporter Ray Long talks about his new book “The House that Madigan Built: The Record Run of Illinois’ Velvet […]

The Chicago Way w/John Kass (03/07/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this edition, Ron Onesti, president of the Joint Civic Committee of Italian Americans discusses why his is angry with Chicago Mayor Lori Lighfoot about her handling of a lawsuit filed by […]

The Chicago Way w/John Kass (03/04/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. Veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin, is back with a reaction to the 22 count indictment levied against former Illinois House Speaker Mike […]

The Chicago Way w/John Kass (03/01/2021): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, Southwest Chicago Alderman. Ray Lopez (15th) to discuss what he calls a ‘media blacklist’ on the 5th floor of City Hall, the brewing scandal of ‘Yolandagate,’ why once staunch supporters […]

The Chicago Way w/John Kass (02/24/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this episode, Kass & Carlin look at the scandal of ‘Chicago Way’ proportions brewing at City Hall in Chicago (this one over a drug bust involving the CPD IAD Chief’s car […]

The Chicago Way w/John Kass (02/21/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. This week, John’s younger brother Nicholas Kass, a retired American diplomat with over 30-years of experience -focused on Aegean/Eastern Mediterranean issues, joins the conversation to talk about international diplomacy, the tensions between […]

The Chicago Way w/John Kass (02/18/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this episode, after news of the first Chicago Alderman named ‘Daley’ being found guilty in federal court, Kass & Carlin are reassured that the ‘Chicago Way’ is alive and well after […]

The Chicago Way w/John Kass (02/14/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this edition, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin looks at the political landscape as the country heads into a mid-term election year […]

The Chicago Way w/John Kass (02/10/2022): During the COVID-19 pandemic, John Kass & Jeff Carlin continue to podcast socially distanced from secure locations. On this episode, Kass presents some startling audio of school board president in Algonquin, IL demeaning parents struggling to deal with the raising kids during a pandemic and the less-than-clear leadership from […]