🗣️New Speaker Announced: Kevin Willer

General Partner, Chicago Ventures

Kevin is a Partner at Chicago Ventures, where he has helped back some of Chicago’s most successful startups, including SpotHero, G2, Cameo, and Project44. A former Google leader and the founding CEO of 1871, Kevin has played a pivotal role in shaping Chicago’s innovation ecosystem. Beyond venture capital, he is an active investor and board member across professional sports. With deep expertise at the intersection of technology, entrepreneurship, and sports, Kevin brings a unique perspective to this conversation.

🎟️ As a member you get 15% OFF any event. Use code: CSTW15 Get your tickets for CSTW: Chicago Sports Tech Week. Tickets are limited based on venue capacitys

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💥Showcase your startup to Chicago's most influential investors and industry leaders.

Direct access to VCs, angels, and corporate venture funds

Concise pitches followed by Q&A with our expert panel

June 30th, 2026 - Application Deadline

July 7th, 2026 - Finalists Announced

July 21st, 2026 - Pitch Competition Day

📍Where:

320 N Elizabeth St, Chicago, IL

✅Submit Your Application Today: Startup Pitch Competition

🎟️ Want to attend? $29 until June 15th. Networking, Food & Beverage all Included. Use code: CSTW15 for additional 15% off at: https://chicagosportstechweek.com/#tickets

🏎️ NASCAR likely making a comeback in Chicago next year, sources say It took NASCAR less than a year to realize Grant Park needed to be featured in its Cup Series. The pros of hosting a race that brought $128 million in total economic impact last year outweighed the cons. The cons were a significant concern, though. Like the nightmare traffic around Lake Shore and Columbus. Or ensuring that the city of Chicago gets a larger share of revenue to cover road work and police services. This concern is one of the main reasons Chicago and NASCAR mutually split for a year, yet conversations between the two continued. Taste of Chicago fans will get to enjoy it at its usual time on July 4th again, as the street race will likely move to Memorial Day weekend. It won’t completely ease street closures and traffic jams in Grant Park, but at least the annual Suenos music festival will have some of the infrastructure already in place. The Tribune features info on how the race was won back and how many people attended the 2025 edition.

🆕rEvolution Welcomes Sophia Snider as Vice President of Media rEvolution knows this very well: to maintain its spot among the best marketing agencies worldwide, it has to keep attracting great talent. Sophia Snider represents just that. Snider comes to rEvolution with close to a decade worth of experience optimizing complex programmatic campaigns for clients like Buick and pharmaceutical company GlaxoSmithKline (GSK). In her previous role at Razorfish, she led high-performing activation teams focused on e-commerce growth and maximizing return on advertising spend (ROAS). The role is a natural progression for Snider as she brings her growing expertise in digital marketing to rEvolution’s Fulton Market headquarters. rEvolution World welcomes Sophia Snider to its team at the link.

🎰Illinois is becoming a battleground for prediction markets. Here’s where things stand. There’s currently no middle ground in Illinois in the debate on prediction markets. Local exchange operators CME Group and CBOE want to be that middle ground. Both are taking efforts to distance themselves from the controversy surrounding operators like Kalshi and Polymarket. State regulators deem the sports contracts they offer to be unregulated sports gambling and seek to stop it. But these operators claim only the CFTC (U.S. Commodity Futures Trading Commission) has the jurisdiction to regulate sports contracts. CME and CBOE have chosen to distinguish themselves from ‘more dangerous’ products. By staying away from sports contracts and leaning on their strong reputations in finance, both hope to remain in good standing with state regulators. Both are committed to the growing event-based trading sector, watching intently while state legislators and other prediction market operators duke it out over semantics and legal jurisdiction. Crain’s covers the battle ensuing in Illinois over prediction markets.

🐻Bears edge closer to move for new stadium in Northwest Indiana Before you roll your eyes at yet another Bears stadium ‘update’, this one’s different. The Bears’ board of directors actually voted on moving forward with a Hammond-based stadium. It’s a major blow to Illinois state legislators who recently failed to approve the Bears’ megaprojects bill in the House. Yet, like many of the franchise's recent ‘updates’, it still doesn’t bring any conclusion to the longest-running soap opera in Chicago sports history. The vote is little more than one of confidence, and the Bears could still choose to remain in Illinois. A self-imposed deadline of late spring/Summer by Bears CEO Kevin Warren is the saving grace to ending a drama-filled era. It’s been one that no one asked for, but that fans, legislators, and taxpayers of Illinois and Indiana are being tortured with. ESPN provides the latest news on the Bears’ stadium saga.

💰Stephen Curry’s Li-Ning deal worth $400 million — and he turned down a bigger offer That might be a new career goal for many: to have the kind of options available that you can turn down offers worth more than you wanted, like Steph did. For Curry, in the latter stages of his NBA career, choosing Li-Ning is about the long-term. The 10-year deal will run through Curry’s 48th birthday. Unless he wants to take on father time as LeBron James does, he’ll be long retired. Li-Ning’s deal with Curry gives him the ability to grow his unique brand while signing male and female athletes. It’s a great deal for him, but you can’t overlook how Under Armor really dropped the ball here. It lost a 13-year relationship with a generational talent who’s been one of the best NBA stars to market. Li-Ning gives Curry even more exposure in China, which could multiply its value when it’s all said and done. The New York Post summarizes the deal and its implications for both sides.

🏫SEC, Big Ten withhold support for landmark college sports bill Not much gets done in college sports without these two power conferences. In opposing the Protect College Sports Act, the SEC and Big Ten are solidifying their view that the bill is incomplete. Their main concerns center on the need for stronger preemption of the various state laws that have emerged since 2021. And the proposed shift of future oversight to Congress, which would slow the process of dealing with a fast-changing landscape. The bipartisan bill was introduced at the end of May and aims to curb some of the wilder elements of today’s college sports, such as seemingly unlimited transfers and athlete eligibility. Even with support from the Big 12 and ACC, the bill has no chance of success unless the two richest conferences are on board. ESPN’s account of the joint statement dives into other concerns the SEC and Big Ten have with the bill.

🇺🇸Knicks, Spurs NBA Finals jerseys to feature 'USA 250' patches to honor America’s 250th birthday Topps is taking a play right out of the Fanatics playbook here. If you’ve been watching the NBA Finals, it’s been hard to miss the vibrant patch featured on each player’s jersey. Once removed after the end of each game, it will be included in ultra-rare trading cards. Scarcity has driven the multi-billion dollar growth of the sports card market after overproduction in the ‘90s killed values. A rematch for the ages of the 1999 NBA Finals between the Spurs and Knicks will almost guarantee to command high valuations. It’s the perfect combo of factors (a rematch 20 years in the making, emerging superstars in Wemby and Jalen Brunson, and America’s 250th birthday) for serious collectors to covet when they become available. The NBA presents the USA 250 patches, along with the volunteer causes it advocates for, as part of the celebrations.

❌MLBPA Says Owners’ Salary Cap Would Cut Player Pay by $500M Any hopes of avoiding a lockout ahead of the expiration of the MLB CBA have gone out the window. In this Front Office Sports article, MLBPA interim executive director Bruce Meyer sounds resolute that the players have been and always will be against a salary cap. Owners and league commissioner Rob Manfred are pushing the salary cap to level the competitive balance in the league and revamp MLB’s broadcasting approach amid the failings of regional sports networks. The MLB has been the only major sports league to resist the owners’ insistence on a salary cap, but not at a small cost. Fears of a repeat of the 1994 season, which resulted in a 232-day stoppage and no World Series that year, are growing. With the expiration date set for December 1st, neither side seems willing to budge.