This week, Chicago turned sports stats into a tradable market, told its next class of lawyers to put AI away, and floated a half-billion-dollar plan to rebuild the Loop around culture. Plus Cloudflare and PostHog are in town next week for AI Tinkerers.

Here’s what’s happening in Chicago:

CME Group is turning sports stats into a financial market.

Last week they announced a long-term partnership with FutureSports, a Chicago startup that converts league-approved play-by-play data into rules-based benchmark indexes, and CME will list futures and options on the FutureSports Performance Indexes.

First monthly and quarterly cash-settled contracts are slated to begin trading this summer, pending regulatory review.

FutureSports frames the buyers as stadium owners and operators, sponsors, insurers, apparel makers, and broadcast partners looking to hedge exposure to a $650B global industry. The methodology is built to align with IOSCO benchmark principles, with leagues serving as official data sources but kept out of index governance.

Starting this fall, first-year students at UChicago Law are barred from using laptops, tablets, and phones in the classroom as part of a broader three-part AI strategy: build AI-resilient pedagogy, elevate the "essential human" skills that distinguish good lawyers, and teach responsible use of the tech.

Dean Adam Chilton's framing is blunt: students will be there with a notebook and a pen.

Professors can name classroom "scribes" to take notes on devices, and allow electronics for things like in-class polling, and legal writing classes will have students draft without AI while using it for research and revision.

It’s less a ban than a bet that oral argument and independent thinking are the skills AI cannot replicate, and UChicago is not alone. Berkeley and UT Austin have moved in the same direction, which makes this a real trend line worth tracking for the AI-in-education pillar

AI Tinkerers Chicago is back on Tuesday August 11th, and this month we're joined by Cloudflare and PostHog for a night built around one of the hardest problems in AI right now: getting products from a working prototype to something that actually holds up in production.

We’re covering the full stack of shipping AI: edge infrastructure patterns for keeping things fast and reliable, the instrumentation and analytics that let teams iterate quickly, and how AI agents can automatically spot product issues, generate fixes, and even open pull requests for review.

Tuesday, August 11, 5:30 to 8:00 PM

Last week I sat down with Lou Raizin to talk through the Cultural Stadium, his $300 to $500M plan to rewire downtown Chicago around arts and culture.

Raizin runs Broadway in Chicago and helped bring Millennium Park to life, along with the Loop Theatre District.

The pitch: instead of one mega-development, treat all of downtown as the stage. He frames culture the way most people frame roads and transit, as infrastructure, and points to McKinsey research on failing post-pandemic downtowns as the reason to move now.

The projects include a hundred smaller interventions stitched together across the Loop.

Free museum access for every kid ages 3-13, a free residency program for up-and-coming artists, a floating farmers market on the river, alleys reborn as public art exhibits, a stretch of Lower Wacker converted into a concert hall, and a glass canopy connecting the buildings along LaSalle Street so the corridor works year round.

This is definitely the most ambitious downtown reinvention Chicago has floated in 20 years, and it sits right at the intersection of culture, real estate, and the foot-traffic problem every Loop employer is tracking.

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