Chicago’s $10 Billion Gamble: Politics, Pensions, and the Portfolio Manager Who Won’t Buy Treasuries

LISTEN and SUBSCRIBE on: Apple Podcasts: https://podcasts.apple.com/us/podcast/watchdog-on-wall-street-with-chris-markowski/id570687608 Spotify: https://open.spotify.com/show/2PtgPvJvqc2gkpGIkNMR5i WATCH and SUBSCRIBE on: https://www.youtube.com/@WatchdogOnWallstreet/featured The City of Chicago is staring down a $1.15 billion deficit, $53 billion in pension debt, and a credit downgrade—yet its treasurer, Melissa Conyers-Irvin, is making headlines for boycotting U.S. Treasury purchases to protest Donald Trump’s immigration policies. Overseeing a $10 billion investment portfolio with a 3.6% annual return, Conyers-Irvin’s move raises eyebrows as she pushes into a Congressional run while critics question her financial acumen, past ethics investigations, and unconventional résumé. Meanwhile, Mayor Brandon Johnson floats new taxes, high-interest borrowing schemes are shot down, and Standard & Poor’s is sounding alarms. This segment dives into the political theatrics, the staggering fiscal reality, and the leadership choices steering one of America’s biggest cities into deeper uncertainty.