I liked the premise of this The Dig podcast, that it was going to tell me why Chicago's left-wing mayor is seemingly so unpopular, but it's very in the weeds and didn't provide much of an overview of the issues. Feels like it's only for people who are already Chicago politics junkies

https://thedigradio.com/podcast/chicagos-left-experiment/

Chicago’s Left Experiment

Featuring Alex Han, Asha Ransby-Sporn, and Alderwoman Jeanette Taylor on Chicago’s left political experiment. In the wake of Zohran’s remarkable victory in New York, organizers all over the country are taking a close look at Chicago under Mayor Brandon Johnson. A Chicago Teachers Union leader elected in 2023, Johnson’s win was the culmination of years of militant labor and social movement struggle. But while much has been achieved, Johnson and his allies have also suffered many defeats–and the mayor’s approval ratings are alarmingly low. In this episode, three long-time local organizers, including a socialist member of city council, analyze the state of the left’s bid for governing power and what broader lessons it holds. Recorded live in Chicago.

The Dig
it got better in the second half!

I didn't realize Chicago also attempted a real estate transfer tax to fund affordable housing (discussed at 1:06:02, it was a referendum that was defeated by the real estate industry in March 2024).

LA passed such a thing, and the real estate industry is now attempting to gut it with a state bill #SB423 (another, #AB698, would make it harder to pass such taxes in future).