Executive Summary
The MillerCoors logo came down off 250 S. Wacker a few weeks ago, replaced by the University of Illinois' new AI center — right next door to the building that already carries the block-I logo. Easy to read as blue-collar past giving way to algorithmic future. I don't think that's what's actually happening.
The people renovating that building are electricians, HVAC techs, and tradespeople — exactly the workers AI can't replace. You can't prompt a burst pipe into fixing itself. Meanwhile I've got a front-row seat, as a PE advisor, to genuinely impressive AI tools that can pattern-match at a scale no human can touch — and none of them can be the person who steadies a family's nerves when the market crashes, or reads a courtroom's shifting energy the way a good trial attorney does.
Twenty-five years ago, I earned my PhD at that same University of Illinois studying how the early internet was rewiring corporate life. The tools change every generation. What Chicago's economy actually runs on — trust, judgment, the ability to read a room — hasn't.

