The Chicago Way

Chicago Way w/John Kass (09/07/26): Co-founder of ‘Chicago Flips Red’ Danielle Carter-Walters joins John Kass & Jeff Carlin to talk about why she is running for mayor, how she was motivated has been burned by the city, and what it takes to stand up to people in her own community. Plus, Kasso wonders if mainstream […]

Chicago Way w/John Kass (09/01/26): Thom Serafin, long-time political strategist, Communicator in Chief of Serafin & Associates, and newly collaborating with Mercury Illinois, joins John Kass & Jeff Carlin to talk about the race for mayor, his lunch with Fidel Castro, and whether or not the Bears will ever get a stadium built. Plus, Kasso […]

Chicago Way w/John Kass (08/24/26): Dan Proft, co-host of “The Morning Answer” radio program 5-9 a.m. on WIND AM 560, joins John Kass & Jeff Carlin to discuss how he’s getting blamed for the demise of the Republican party in Illinois for some reason, what happens when Illinois Democrats realize the whole system is collapsing […]

Chicago Way w/John Kass (08/17/26): Businessman and philanthropist Willie Wilson joins John Kass & Jeff Carlin to talk about why he wants to run for Chicago mayor again, who he thinks is ‘mentally ill’ for questioning his reasons, and what he thinks about people running for two offices at once. Plus, Kasso wonders if Michael […]

Chicago Way w/John Kass (08/10/26): Charles Lipson is back, joining John Kass & Jeff Carlin to discuss why ‘democratic socialism’ is on the rise in the United States, who is pushing this shift within the Democratic Party, and what it means for the future of the republic. Charles is the Peter B. Ritzma Professor of […]

Chicago Way w/John Kass (08/03/26): This week, Dr. Cory Franklin – who spend over 25 years at Cook County Hospital in Chicago, joins Jeff Carlin to make sense of what Dr. Anthony Fauci did wrong, why he’s in the hot seat now, and when – if ever – modern science & medicine will recover from […]

Chicago Way w/John Kass (07/27/26): Old friend and former boss at WLS-AM, Drew Hayes, joins John Kass and Jeff Carlin to talk about what the differences are between California and Illinois, how media has changed over the years, and what can be done to revive radio. Plus, Kasso wonders how we can rekilter the way […]

Chicago Way w/John Kass (07/20/26): John Kass & Jeff Carlin take a look a the rise of “agenda journalism” in media, what happens when teachers focus on activism instead of education, and why California should be a cautionary take for Illinois. Plus, Kasso wonders if the rise in violent activism is related to Randi Weingarten’s […]

Chicago Way w/John Kass (07/13/26): John Kass & Jeff Carlin welcome retired Chief of Detectives for the Chicago Police Department, Gene Roy, to discuss how dishonorably the outgoing Supt. Larry Snelling was treated by Mayor Brandon Johnson, what it’s like working in an understaffed district, and who should be tabbed to take of the CPD. […]

Chicago Way w/John Kass (07/07/26): Happy Birthday America! Charles Lipson joins John Kass & Jeff Carlin for a look at who is pushing the narrative that the US is bad, why people can’t seem to agree on common sense anymore, and what is at risk if we dismantle institutions like the Constitution. Charles is Professor […]

Chicago Way w/John Kass (06/30/26): John Kass & Jeff Carlin are back this week to dive into what the current state of American culture means to the rest of the world, how failures that stack up when we elect/hire/listen to unqualified leaders, and a stack of questions from listeners. Plus, Kasso is VERY confident the […]

Chicago Way w/John Kass (06/22/26): Re-Issue: Episode #6 from 02/10/206. Cartoonist Scott Stantis joins John Kass & Jeff Carlin to discuss what turns out to be the end of Rahm Emanuel’s tenure as Chicago Mayor, the 2016 primary season featuring Hillary Clinton vs. Bernie Sanders & Donald Trump vs. establishment everything, and meet two drivers […]

Chicago Way w/John Kass (06/15/26): John Kass & Jeff Carlin are together to talk about the things we don’t talk about when violence happens, how Chicago Democrats let the Bears go to Indiana to save face, and why the Obama Presidential Center allegedly owes people money, already. Plus, Kasso remembers the first time meeting his […]

Chicago Way w/John Kass (06/08/26): John is off this week, celebrating his son’s wedding, so we bring you a reissue from January of 2016. The first episode, featuring John Kass, Will Lee, and Jeff Carlin, talking about a strange hat controversy at a local TV station, bizarre news stories on TV, Will’s amazing story about […]

Chicago Way w/John Kass (05/31/26): Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin with questions about Chuy Garcia’s old school political tactics, whether or not Brandon Johnson has the heart to run for re-election, and why his fellow alders are finally getting behind his proposal to hold parents of violent teens accountable? Also, […]

Chicago Way w/John Kass (05/26/26): John Kass & Jeff Carlin celebrate the bravery it takes to face violent warm summer nights in Chicago in the face of gang wars and ‘teen takeovers.’ Plus, Kasso has a ‘Happy’ pet peeve. Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow @JPCarlin Download this episode here by using […]

Chicago Way w/John Kass (05/18/26): John Kass & Jeff Carlin are joined by former (possibly, future?) candidate for Mayor of Chicago, head of the public school systems in Chicago, Philadelphia and the Louisiana Recovery School District, Paul Vallas to talk about recent attacks on him, who he thinks might be behind it, and what he […]

Chicago Way w/John Kass (05/11/26): John Kass & Jeff Carlin remember his late mother, Betty Kass, and as she would have wanted, move on to the ugly Obama Presidential Center building, Chicago alders wanting Walgreens to be criminally charged for closing stores, and Stephen Colbert smirking his way through a farce of an interview with […]

Chicago Way w/John Kass (05/05/26): On this episode, revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin to discuss how tipping became an american tradition and what it means to the industry. Plus, Kasso wonders if there is a trick to surviving Mother’s Day at a restaurant? Follow Everything John Kass – JohnKassNews.com […]

Chicago Way w/John Kass (04/27/26): John Kass & Jeff Carlin tackle news of the week including a Chicago Police officer being killed in the line of duty, chaos at the White House Correspondents’ Dinner, and news former Mayor Richard M. Daley is recovering from a stroke. Plus, Kasso wonders if the Chicago Teachers’ Union take […]

Chicago Way w/John Kass (04/20/26): Nicholas S. Kass joins John Kass & Jeff Carlin to talk about his latest piece, Keep the Kurds Out of the Iran War, in the American Conservative. Nick is John’s younger brother and served in the U.S. government for over 30 years at the White House/National Security Council, State Department, […]

Chicago Way w/John Kass (04/13/26): John Kass is back with Jeff Carlin to catch up on some big news from John’s brother Nick, our friend Sal Carmada, and a budding feud on JohnKassNews.com. Plus, Kasso urges everyone to take of your heart, your spiritual heart. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, […]

Chicago Way w/John Kass (04/06/26): Charles Lipson joins Jeff Carlin (John Kass is out this week) to talk about how war in Iran will alter President Donald Trump’s legacy as Commander-in-Chief Charles. Charles is the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago and an author whose writings can be […]

Chicago Way w/John Kass (03/30/26): This week, John Kass & Jeff are joined by Rafael Mangual, the Nick Ohnell Fellow and head of research for the Policing & Public Safety Initiative at the Manhattan Institute and a contributing editor of City Journal. On the docket, why Democrats make excuses for violent crimes, ignore the pain […]

Chicago Way w/John Kass (03/23/26): Former State Rep. Tom Morrison is here to talk about his ‘complete ​blueprint for winning ​a local or state race’ at CandidateMasterclass.com and why it is so important as the country prepares to mark the 250th anniversary of the signing of the Declaration of Independence, everyone takes an active role […]

Chicago Way w/John Kass (03/17/26): This week, the Honorable Judge James R. Brown (ret.) returns to the podcast with Brendan Philbin, Senior Counsel at the Liberty Justice Center, to discuss a federal civil rights lawsuit filed on behalf of Judge Brown, who was removed from his judicial recall appointment after Illinois Supreme Court justices retaliated […]

Chicago Way w/John Kass (03/10/26): Dan Proft, co-host of “The Morning Answer” radio program 5-9 a.m. on WIND AM 560, is this week’s guest joining John Kass & Jeff Carlin to discuss the Illinois governor’s race, specifically the Republican primary that has seen second-time candidate Darren Bailey take umbrage with Dan being paid to work […]

Chicago Way w/John Kass (03/03/26): John Kass is back. John joins Jeff Carlin to talk about what’s kept him away and what’s next. Plus, Kasso wonders if we really appreciate what we have? Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. […]

Chicago Way w/John Kass (02/23/26): Nicholas Kass steps in for Jeff Carlin & John Kass as illness plagues the Kasso-sphere to present one of his favorite JohnKassNews.com columns, Riding a Good Horse in the Snow, Part 2. Nick is a regular contributor and, most notably, a retired U.S. Foreign Service officer, diplomat, and Intelligence expert […]

Chicago Way w/John Kass (02/16/26): Mike “Houli” Houlihan, a well-known Irish-American actor, filmmaker, stand-up comedian, and former Chicago Sun-Times columnist, joins Jeff Carlin while John Kass regains his voice. Houli has a new piece on JohnKassNews.com and is always working on multiple projects at Hibernian Media. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, […]

Chicago Way w/John Kass (02/09/26): Charles Lipson is back playing pinch-hitter for John Kass, who lost his voice educating bright young minds at Hillsdale College, and joins Jeff Carlin with a dive into how we quantify trust. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X (Twitter). Tell your friends about us. […]

Chicago Way w/John Kass (02/02/26): RealClear Politics’ Tom Bevan is here to discuss how we got ourselves to tenuous climate in American politics, what we can learn from his Princeton senior thesis, and why Don Lemon is going to be okay, even if he tells you different. Plus, Kasso wonders if there is a more […]

Chicago Way w/John Kass (01/26/26): Retired police chief Tom Weitzel (Riverside) joins John Kass & Jeff Carlin to talk about his work with Awake Illinois to stop SB2820 (Introduced by Sen. Laura Fine [D-Glenview]) from being passed. SB2820 would ban anyone who previously worked with Immigration and Customs Enforcement (ICE) from being a law enforcement […]

Chicago Way w/John Kass (01/19/26): To mark the tragic anniversary of his daughter’s death, Glenview native Joe Abraham joins John Kass & Jeff Carlin to talk about his gut-wrenching experience losing his daughter Katie when she was killed in a hit-and-run crash, allegedly caused by a Guatemalan national who was in the country illegally and […]

Chicago Way w/John Kass (01/12/26): Thom Serafin, long-time political strategist, Communicator in Chief of Serafin & Associates, & newly collaborating with Mercury Illinois, joins John Kass & Jeff Carlin with some much needed perspective on who are the Cook County Bar Association & the Chicago Council of Lawyers, and why are they upset over a […]

Chicago Way w/John Kass (01/05/26): This week, Charles Lipson joins John Kass & Jeff Carlin to start off the new year. Charles is the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago and an author whose writings can be found in the Spectator, Spectator World, The Telegraph, and more. On […]

Chicago Way w/John Kass (12/30/25): Happy New Year from the Chicago Way. John Kass & Jeff Carlin look at the end of the year and who might be eligible for the first-ever Moutza of the Year. Obvious contenders are Chicago Mayor Brandon Johnson, Cook County Board President Toni Preckwinkle, and Illinois Governor JB Pritzker, but […]

Chicago Way w/John Kass (12/24/25): Merry Christmas, Kyrie Elaison. John Kass reads ‘O Holy Night,’ his annual Christmas column. Blessings to all! Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X (Twitter). Tell your friends about us. Join the great adventure. Subscribe today! Follow Everything John Kass – JohnKassNews.com Follow @John_Kass Follow […]

Chicago Way w/John Kass (12/19/25): Greetings, good tidings, and cheer from John Kass & Jeff Carlin at The Chicago Way podcast. In this last collab before the traditional Christmas column reading, John sets the table for a Kass family soup competition. Plus, Kasso shares the story of our dearly departed Zeus the Wonderdog enjoying too […]

Chicago Way w/John Kass (12/15/25): Austin Berg, Executive Director of the Chicago Policy Center at the Illinois Policy Institute, join John Kass & Jeff Carlin with a look at just how badly Mayor Brandon Johnson has managed Chicago’s finances and the inane ideas the Mayor has come up with to fill a nearly $1.2 billion […]

Chicago Way w/John Kass (12/08/25): Pastor Corey Brooks joins John Kass & Jeff Carlin to discuss how his fundraising effort to walk across the entire United States in a year is going, why he has zero confidence in Chicago Mayor Brandon Johnson, what former mayor Daley said to him, and where he’s been eating along […]

Chicago Way w/John Kass (12/01/25): This week, retired Police Chief, Tom Weitzel (Riverside), joins John Kass & Jeff Carlin to talk about who is to blame for the release of veteran convict Lawrence Reed –who allegedly poured gasoline over 26-year-old Bethany MaGee at random, setting her on fire aboard a Blue Line train– and what […]

Chicago Way w/John Kass (11/24/25): Thanksgiving is upon us, but senseless violence continues to plague the city, and John Kass wonders if the judges who let career violent criminals back on the street to destroy more lives will ever be held accountable? Kasso is thankful for a good cup of Kribi Coffee and supports their […]

Chicago Way w/John Kass (11/17/25): Paul Vallas is here to talk about his latest column- “Chicago’s Killing Fields”, Mayor Brandon Johnson’s awful policies, and the time he played the role of Barney. Plus, Kasso remembers his time in the saddle and a good horse. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or […]

Chicago Way w/John Kass (11/11/25): Chicago Ald. Ray Lopez (15th) is here to explain his amnesty plan to John Kass & Jeff Carlin and discuss why he’s not surprised Chuy Garcia used old-school machine politics to retire on another public pension and coronate his ‘Leftino” successor. Plus, Kasso welcomes Kribi Coffee into the fold. Check […]

Chicago Way w/John Kass (11/03/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin this week to discuss what Zohran Mamdani’s role as a leader of the modern Democratic Party will look like, how the U.S. is going to respond to the […]

Chicago Way w/John Kass (10/28/25): This week, John Kass & Jeff Carlin wax philosophically about how the U.S. found itself in revolutionary times and where do we go from here. Plus, Kasso wonders if New York is ready for what it’s voting for? Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X […]

Chicago Way w/John Kass (10/20/25): RealClear Politics’ Tom Bevan is here with a post-op on what impact the “No Kings” rallies (Chicago’s rally featured one of Illinois’ top gamblers -Gov. JB Pritzker (D), for whom Tom has a some choice words) will have, why he thinks this government shutdown will break the 2018-2019 shutdown record […]

Chicago Way w/John Kass (10/13/25): This week, Garry McCarthy – former Chicago Police Department (CPD) Superintendent and current Chief of Police for Willow Springs, IL- joins John Kass and Jeff Carlin to discuss a disturbing dispatch call involving CPD, Customs and Border Protection (CBP), Immigration and Customs Enforcement (ICE), Cook County Sheriffs, & Illinois State […]

Chicago Way w/John Kass (10/06/25): Fall is officially here and so is story time. John Kass tells Jeff Carlin about standing outside Wrigley Field in 1984 and the series of events that lead him there. Plus, Kasso gets an apology. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, or on X (Twitter). Tell your […]

Chicago Way w/John Kass (09/29/25): This week, the Honorable Judge James R. Brown (ret.) joins John Kass & Jeff Carlin to talk about the moment soon-to-be-former Chief Judge Timothy Evans gathered bond court judges to direct them to go against the rule of law and let violent offenders off easy, lest the judges be reassigned. […]

Chicago Way w/John Kass (09/22/25): Dan Proft, co-host of “The Morning Answer” radio program 5-9 a.m. on WIND AM 560, is this week’s guest joining John Kass & Jeff Carlin with a breakdown of the FCC meddling in the Jimmy Kimmel fiasco and what it will take to push the JB Pritzkers of the world […]

Chicago Way w/John Kass (09/15/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin to talk about the cold-blooded murder of Charlie Kirk and how free speech in the UK is under threat. Plus, Kasso wonders if the Democrat culture of assassination […]

Chicago Way w/John Kass (09/08/25): Newly minted candidate for Illinois Governor Ted Dabrowski of Wirepoints joins John Kass & Jeff Carlin to lay out his plan for convincing the center left & independent voters of the state to help him beat Gov. JB Pritzker in next year’s election. Plus, Kasso wonders if this is the […]

Chicago Way w/John Kass (09/01/25): This week, former Cook County and federal prosecutor Bob Milan joins John Kass & Jeff Carlin to talk about his original plan from 10 years ago to bring in National Guard troops to tamp down the weekly number of shootings in Chicago and how this strategy might work today. Plus, […]

Chicago Way w/John Kass (08/25/25): Glenview native Joe Abraham joins John Kass & Jeff Carlin to talk about his gut-wrenching experience losing his daughter Katie when she was killed in a hit-and-run crash, allegedly caused by a Guatemalan national who was in the country illegally and is suspected of driving under the influence, Julio Cucul […]

Chicago Way w/John Kass (08/18/25): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin with a look at how President Barack Obama’s misdeeds compare to Richard Nixon, what candidate for mayor Zohran Mamdani means for NYC, and whether voters will ever get out from the stranglehold of the Iron Triangle deception created […]

Chicago Way w/John Kass (08/11/25): This week, John Kass & Jeff Carlin tackle JB Pritzker’s hypocrisy when it comes gerrymandering, evidence that President Barack Obama was trying to convince people Russia got Trump elected in 2016 -even though we know they didn’t, and look at why dreams of living on the Moon or Mars are […]

Chicago Way w/John Kass (08/04/25): Chicago Alderman Brendan Reilly (42nd) joins John Kass & Jeff Carlin to announce that his circulating petitions and seriously considering running against Cook County Board President Toni Preckwinkle. Ald. Reilly talks about wanting to course correct years of democratic socialist policies that have left the county broke & bloated. Plus, […]

Chicago Way w/John Kass (07/28/25): This week, Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin to discuss how Mayor Brandon Johnson has let flooding plague the city, year after year, while he spends time picking fights with President Donald Trump. Ray also wonders if intellectual curiosity is dead and why Chicago’s voter rolls seem […]

Chicago Way w/John Kass (07/21/25): On this episode, Ted Dabrowski of Wirepoints.com joins John Kass & Jeff Carlin to highlight how Governor JB Pritzker is delusional about Illinois’ status as an ‘economic powerhouse’ and to warn the voters of New York City about the perils of electing unserious socialists. Plus, Kasso offers a hat-tip to […]

Chicago Way w/John Kass (07/07/25): Charles Lipson joins John Kass & Jeff Carlin for this post Independence Day episode. Charles is the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago and an author whose writings can be found in the Spectator, Spectator World, The Telegraph, and more. On the docket, […]

Chicago Way w/John Kass (06/30/25): On a HOT summer Sunday, John Kass & Jeff Carlin head out to the first annual Sicilian Summer Block Party in the Dunning neighborhood to break bread and enjoy some entertainment. Along the way, fans of John’s share stories about what the Chicago Way means to them. Plus, Kasso tells […]

Chicago Way w/John Kass (06/23/25): On this episode, revered Chicago restaurateur Jimmy Banakis joins John Kass & Jeff Carlin with a look at the history of the ‘Chicago Way’ -alderman, committee men, cops, etc. shaking down small biz- and how it personally has impacted his family through the generations. Plus, Kasso wonders if business as […]

Chicago Way w/John Kass (06/16/25): This week, John Kass & Jeff Carlin are pleased to welcome Sal Camarda from Joseph’s Finest Meats to talk about his family’s tradition of bringing the best quality meats, sausages, and more to Chicago. Sal, along with his brother Ben, are second generation proprietors and enjoy being part of the […]

Chicago Way w/John Kass (06/09/25): Prof. Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago (whose writings can be found in the Spectator, Spectator World, The Telegraph, and more), is here to explain why Democrats keep ending up on the wrong side of ’80/20 problems’ and how American culture […]

Chicago Way w/John Kass (06/02/25): This week, John Kass & Jeff Carlin discuss the merits of President Donald Trump commutating the federal sentence of notorious gang kingpin Larry Hoover and feds seeking to put former Illinois Speaker of the House Mike Madigan in jail for 12 years at the age of 83. Plus, Kasso urges everyone […]

Chicago Way w/John Kass (05/27/25): This week, John Kass tries to get to the bottom of Jeff Carlin’s bad mood by sharing stories from his weekend in the city celebrating his wedding 39th wedding anniversary. Plus, Kasso wonders if his love for Chicago can ever be redeemed. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, […]

Chicago Way w/John Kass (05/19/25): RealClear Politics’ Tom Bevan is here to discuss James Comey selling seashells by the seashore and what could be considered one of the greatest scandals in presidential history, the cover-up of Joe Biden’s health problems. John Kass & Jeff Carlin also ask Tom about Rahm Emanuel facing off against JB Pritzker in […]

Chicago Way w/John Kass (05/12/25): This week, Ald. Ray Lopez (15th) joins John Kass & Jeff Carlin to look at why he thinks Chicago Mayor Brandon Johnson perpetuating a patronage scheme by steering ‘PlayStreets’ contracts away from Latino wards and into wards where Mayor Johnson is trying to curry favor. Also, Ald. Lopez also hints […]

Chicago Way w/John Kass (05/05/25): This week, former CEO of the Chicago Public Schools (1995-2001) & candidate for mayor, Paul Vallas joins John Kass & Jeff Carlin with a look at how Governor JB ‘Master Oligarch of Illinois’ Pritzker is doing running the state and shares a stories about being brought before the him to […]

Chicago Way w/John Kass (04/29/25): On this edition, veteran political advisor at Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins John Kass & Jeff Carlin with an analysis of how Sen. Dick Durbin announcing he won’t run for reelection will shuffle the deck in Illinois politics and what Illinois Governor JB Pritzker’s […]

Chicago Way w/John Kass (04/20/25): John Kass takes time to talk about the meaning of Easter (it’s not really about chocolate bunnies and jelly beans) and what it means to his family. From John Kass & Jeff Carlin, Happy Easter, blessings of love. Christos Anesti! Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, or Facebook, […]

Chicago Way w/John Kass (04/14/25): This week, Charles Lipson is back to talk about how education has changed and how it is impacting institutions of higher learning. Charles is the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago and he joins John Kass and Jeff Carlin for a lively discussion. […]

Chicago Way w/John Kass (04/07/25): This week, John Kass & Jeff Carlin tackle the often violent ‘street takeovers’ plaguing Chicago’s business district, President Donald Trump’s policy of raising tariffs to put an end to ‘globalization,’ and various district court judges blocking executive actions by President Trump. Plus, Kasso wonders why Chicago’s city leaders are afraid […]

Chicago Way w/John Kass (03/31/25): On this episode, author and retired director of medical intensive care at Cook County Hospital in Chicago for over 20 years, Dr. Cory Franklin joins John Kass & Jeff Carlin to discuss why the JFK assassination has captivated conspiracy theorists and the general public for decades and what we, if […]

Chicago Way w/John Kass (03/24/25): John Kass & Jeff Carlin tackle Chicago Mayor Brandon calling himself the second coming of Harold Washington, his campaign donations from a law firm involved in a lawsuit with the city, and how begging for a 3% kickback from city vendors is working out. Plus, Carlin has an early nominee […]

Chicago Way w/John Kass (03/17/25): A newcomer to the podcast, Chicago Police Chief of Detectives (ret.) Gene Roy joins John Kass & Jeff Carlin to talk about how wearing a badge in Chicago has changed over the last forty years and look at what he sees as major flaws with the criminal justice & courts […]

Chicago Way w/John Kass (03/10/25): Charles Lipson, joins John Kass & Jeff Carlin this week. Charles is the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago and an author whose writings can be found in the Spectator, Spectator World, The Telegraph, and more. On the docket, President Trump’s address to […]

Chicago Way w/John Kass (03/03/25): Nicholas S. Kass joins John Kass & Jeff Carlin on the last episode to discuss the momentous blowup between President Donald Trump & President Volodymyr Zelenskyy at the White House and what this means for the future of Europe and NATO. Check out more from Kass at JohnKassNews.com or contact me at john@johnkassnews.com, […]

Chicago Way w/John Kass (02/24/25): New York Post columnist Miranda Devine joins John Kass and Jeff Carlin to discuss President Trump’s breakneck first month back in office and why bulldogs like Kash Patel & Elon Musk have the Deep State reeling from the breadth and scope of their efficiency. Plus, Kass wonders if an English Bulldog should be […]

Chicago Way w/John Kass (02/17/25): This week, John Kass & Jeff Carlin take on the week’s news, starting with the long-awaited guilty verdict in People v. Michael J. Madigan and ending with tear-jerking film recommendations. Also on the docket, ex-governor Rod Blagojevich was back in the headlines after receiving a full pardon from President Donald […]

Chicago Way w/John Kass (02/10/25): Just in time for Valentine’s Day, Ald. Ray Lopez (15th) explains the special purpose room that houses a bounty of gifts on the 5th Floor of Chicago City Call and why he thinks it will take someone special to help Chicago course-correct before it’s too late. Plus, Kasso wonders who […]

Chicago Way w/John Kass (02/03/25): This week, a retired American diplomat with over 30 years of experience advising the most powerful leaders in the world on security matters and who also happens to be John’s younger brother, Nicholas S. Kass, joins John Kass & Jeff Carlin to talk about why he signed his name to […]

Chicago Way w/John Kass (01/27/25): Charles Lipson, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, joins John Kass and Jeff Carlin this week with a focus on President Donald Trump’s ‘First Hundred Hours,’ his trips to North Carolina & California, and what pushback from within the GOP he might […]

Chicago Way w/John Kass (01/20/25): Inauguration Day is here and so is Dan Proft, co-host of “The Morning Answer” radio program and host of ‘Counter Culture’ podcast, to join John Kass & Jeff Carlin with a look at what Lawfare ‘retribution’ and ‘vengeance’ the Trump Administration will dole out with the likes of Kash Patel […]

Chicago Way w/John Kass (01/13/25): On this episode, Austin Berg is here from the Illinois Policy Institute to explain why Chicago needs a charter, a new mayor, and better fiscal sense to John Kass & Jeff Carlin. Plus, Kasso wonders if Idiot Wind(s) is a only a coastal concern? Check out more from Kass at JohnKassNews.com or […]

Chicago Way w/John Kass (01/06/25): In the first episode of 2025, John Kass & Jeff Carlin try to make sense of this year’s collection of the Presidential Medal of Freedom recipients, look forward to what 2025 has in store, and share a couple of recipes for staying warm. Plus, Kasso offers up a couple of […]

Chicago Way w/John Kass (12/30/24): Joining John Kass & Jeff Carlin on the last episode of 2024 is a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on Middle East security matters and who also happens to be John’s younger brother, Nicholas S. Kass. The discussion centers […]

Chicago Way w/John Kass (12/23/24):  On the Christmas Edition, John Kass & Jeff Carlin are joined by Jude Russo, the managing editor of The American Conservative, with a look at how the President-elect Donald Trump’s challenges in 2025 and what it means be a conservative in the modern Republican party. Plus, Kass has a Christmas […]

Chicago Way w/John Kass (12/16/24): On this edition, Ald. Ray Lopez (15th) discusses what it takes for Chicago Mayor Brandon “Brandito” Johnson to have his approval rating drop to 14% and whether or not Lopez & the coalition of Alders opposing Johnson’s rubberstamp agenda can protect the citizens from another ‘parking-meter-esque’ budget deal. Plus, Kasso wonders […]

Chicago Way w/John Kass (12/09/24): This week, the Peter B. Ritzma Professor of Political Science Emeritus at the University of Chicago, Charles Lipson, joins John Kass and Jeff Carlin to talk about his latest piece writings, President-elect Donald Trump’s transition to power, and what Republicans must do now that they have all the cards. Plus, […]

Chicago Way w/John Kass (12/02/24): In a post Thanksgiving hangover, John Kass & Jeff Carlin look at what’s next for the mainstream media and ruling class in Washington, Illinois, & Chicago after Donald Trump takes office. Plus, Kasso gets a couple of book suggestions: The Iron Heel & The Elite. Check out more from Kass […]

Chicago Way w/John Kass (11/25/24): Joining John Kass & Jeff Carlin this week is a veteran, mother, politician, and conservative radio voice in Illinois, Jeanne Ives to talks about the need for Republicans in Illinois to stand up to Gov. JB Pritzker, what Donald Trump’s second term as President will mean for corruption in Illinois, […]

Chicago Way w/John Kass (11/18/24): As Donald Trump loads up his cabinet with his most loyal supporters, the man behind Serafin & Associates and co-host of The Crisis Cast, Thom Serafin joins Jeff Carlin and John Kass with a look at how voting demographics shifted in 2024 and what that means for Trump’s early days […]

Chicago Way w/John Kass (11/11/24): Joining John Kass & Jeff Carlin this week is a retired American diplomat with over 30-years of experience advising the most powerful leaders in the world on security matters and who also happens to be John’s younger brother, Nicholas S. Kass. On the docket, Nick lays out what’s next for […]

Chicago Way w/John Kass (11/04/24): As the 2024 election cycle winds down, RealClear Politics’ Tom Bevan is here with an analysis of polls, pandering, & punditry. Tom join John Kass & Jeff Carlin with a look at what happens when polls don’t match results and a preview of RealClearPolitic‘s election night live coverage feat. Carl […]

Chicago Way w/John Kass (10/28/24): As Donald Trump rallies his base at Madison Square Garden & Kamala Harris sends Hillary Clinton on the attack, John Kass & Jeff Carlin what happens to the Democrats if things don’t go their way. Plus, Kasso wonders if the ‘F-word’ should be thrown around by those who know nothing […]