Ben confronts, sorta, a grumpy old, white guy at the Jazz Festival. Oh, Chicago, why must you be the way you are? Meet Debby Pope, candidate for school board in district 2B on the north side. Think Bernie Sanders running for school board. Hear about her journey from Erasmus High School—in Brooklyn—to Chicago, where she was a public school teacher for many years.

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In the category of—wow, that’s some really serious passive aggressive behavior, Congressman Bost blows Darren Bailey’s cover. Ben riffs. Alderwoman Nicole Lee tells you everything you need to know about the monstrosity of a proposal that would put a rail yard in Bridgeport and build a new Sox stadium in the west loop. One of the dumbest ideas since the parking meter deal. Speaking of which—Nicole explains the latest on that front. Nicole is the alderwoman of the 11th Ward, where the current Sox Park is located.

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The Hulu show Furious is Dirty Harry for liberal millennials. Ben riffs. David talks Furious, oligarchs, AI, MAGA’s midterm convention, Trump’s ongoing insanity, and the state of John Fetterman. Also, Trump’s latest promise to give us money. David is a political science professor at Roosevelt University and a columnist for The Nation. His views are his own.

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With another Bears season upon us, Ben makes a pledge—if the Bears move to Indiana, he will call them the Hammond Bears. Forever and a day. Tim Shaer talks Bears and brings Ben back to earth—they ‘re aren’t moving to Hammond, people. But first, they get sidetracked on a tangent about Jerry Krause. Yes, two Boomers talking ancient sports history. Stick around for the great White Sox stadium debate. Tom is a former NBC sports anchor and host on The Score.

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Mayor Mamdani has a unique strategy for dealing with the legacy media—he bypasses them. Ben riffs. Hilario Dominguez makes his debut, explaining why he’s running for school board president and his position on everything from school closings to school lunches to TIFs and dealing with powerful mayors. Hilario is a former special ed teacher, CTU political director and proud graduate of Whitney Young High School.

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Untold billions in dark money is funding MAGA efforts to hold on to the Senate. Ben riffs. Jessica Biggs makes her debut. Talking about her candidacy for school board president. How she was punished by Mayor Rahm’s school flunkies for daring to speak out for clean schools. And the need to be independent of the mayor—even an all powerful one like Daley or Rahm—on TIFs. Also, a few words about charters, magnets and neighborhood schools. Jessica is currently on the Chicago school board.

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Caleb & Caleb & PCA, it’s magic time in Chicago sports. Unrivaled since, dare I say, 1984. Ben riffs. Miles Porter takes the deep dive on the Cubs and Sox as they head into the final days of the regular season. The good news is they’re doing better than anyone expected. The bad news is—well, let’s not think about the bad news. Miles co-hosts the baseball podcast, Blue Line Radio.

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One week before Mayor Johnson announced he’s running, Ben’s source tells him he’s running. Yes, Ben has a source. Ben riffs. Podcaster Marc Sims explains all. Including…why so many white people just can’t bring themselves to vote for Mayor Johnson. And what Abdul El-Sayad needs to do to win the Black vote. And what is the Democratic Establishment. And why do fools fall in love. Ok, maybe he has no answer for that. Marc hosts the podcast Just A Few Questions.

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