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 clique of candidates is ready for an outsider?

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 wonders who else could be considered a skunk at the garden party?

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 around them, and what the 2028 election cycle will look like. Plus, Kasso wonders if voters in the 2026 Chicago mayoral election realize they’re all Augustus Gloop?

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 ‘Jaws’ Giorango is still on good terms with Alexi Giannoulias?

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 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. Plus, Kasso offers an update on his health.

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 this crisis.

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 people absorb information.

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 role at the American Federation of Teachers?

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. Plus, Kasso wonders if the next mayor of Chicago will have what it takes to set things right?

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 Emeritus of Political Science at University of Chicago and you can read him at CharlesLipson.com Plus, Kasso is wonders if anyone noticed Chicago Police Supt. Larry Snelling fleeing the sinking ship that is Mayor Brandon Johnson’s tenure?