🌍 Looking to Connect With More People Across the Chicago Sports World?

🍻 Check out the recap of our Happy Hour Last Week. There were over 80 people in attendance connecting with others in the sports business community. Chicago Sports Tech Happy Hour brought together founders, investors, operators, and sports innovators for an evening of networking, conversation, and community-building. The event highlighted the growing momentum around Chicago’s sports tech ecosystem and created space for new partnerships, ideas, and opportunities to emerge. Overall, it was a strong reminder that Chicago has the talent, ambition, and network to become a major hub for the future of sports innovation.

🐻Cubs Score Another Win in Wrigley View Rooftop Fight.

It costs millions to prepare and broadcast a home game at Wrigley for fans to see in person. That doesn’t include payroll and money spent on the manager or other supporting staff. Wrigley View Rooftop, located across the street from the Friendly Confines, has tried to sidestep any revenue-sharing agreements the Cubs had with surrounding businesses offering rooftop seating. This latest victory allows the team to take the case to court, despite Wrigley View Rooftop saying the team is overstepping its authority. The club first launched the lawsuit in 2024 after catching wind of Wrigley View’s scheme. The Cubs don’t own the air or building Wrigley View operates in, it claims. Bold rebuttal, but unsuccessful. The case is headed full steam ahead for trial after the judge denied a motion to send it to arbitration. Inflation already eats into the team’s profits (and everyone’s); they aren’t about to let free-riding continue to do the same. Sportico reports on the Cubs’ 2026 payroll and specifics on why the case is moving forward to trial.

🚧Tax Break for United Center’s 1901 Project Advances amid Union Pushback.

As the 1901 Project gains momentum, Near West Side residents are still voicing concerns about how much the project will actually benefit them. Billions will pour into the area, but whether it will be a net positive for locals is the main question. Some union members oppose a corporation receiving a multi-million-dollar property tax incentive while local property taxes have been on the rise. And the aldermen of the 7th and 10th wards are questioning whether diversity goals will be met before construction begins. One thing is for sure: if construction delays deep into the summer, financial backers won’t be happy. Especially if this winter is as brutal as the last. The Bears and other local teams have learned that the City Council reacts adversely to large property tax incentives. The United Center owners seem to have more support for their property tax incentive ask, but the clock is still ticking. The project could face a stiff battle before widespread acceptance, potentially causing further delays in construction. Crain’s discusses the magnitude of the incentive for the 1901 Project and exactly why some local leaders oppose it in its current form.

🛼Retro Roller Rink Coming To Navy Pier This Summer.

In some ways, the old Crystal Gardens venue will reconnect people to their physical environment like it used to. Crystal Gardens, with its lush palm trees and monstera plants, gave way to the digitally enhanced tech exhibit Illuminarium after COVID. The palm trees aren’t coming back, but people will put on rollerblades and kneepads while avoiding an embarrassing fall instead of gazing at 4K interactive laser-projected images. Summer Skate will debut at Navy Pier in June and run through Labor Day. It’s the city’s first lakefront roller rink. Retro is the theme of the sport and the pop-up venue. It will feature arcade games and a 90’s vibe with plans to introduce special themed events that dive into other eras. You don’t even have to be an avid roller skater to like the idea: Navy Pier in the summer, with its lakefront views, is hard to beat anywhere in the city. Block Club Chicago mentions the company Navy Pier is partnering with, and provides a full scope of what the arrangement entails.

🏟️McDonald’s, Chicago Fire Strike Naming Rights Deal for South Loop Stadium.

“Fire Up” is more than just a team motto. The Fire is a club on the rise. Its stadium is under construction, and its new state-of-the-art training facility opened last March. A huge co-sign by one of the most recognizable brands worldwide is transformative. It’ll provide a sizable revenue stream to the Fire, unavailable to them in the past as tenants at Soldier Field or in Bridgeview. It also makes for a powerful local marketing partner. For McDonald’s, it’s the perfect time for them to venture into their first-ever naming rights sponsorship deal for a pro sports stadium. It was hard to believe it hadn’t had one before, but there’s no better way to get into the business than by supporting a fellow Chicago-based business. Both companies will be anxious for the expected opening of McDonald’s Park in 2028. It’s a milestone date, marking their entry into a new era. Crain’s provides renderings of the future stadium and more info on the naming rights deal.

🩺Fitness Wearable Whoop to Offer On-Demand Clinician Access to U.S. Users.

Whoop has exploded from a $50 million company 10 years ago to one valued at $10.1 billion today by putting innovation at the forefront. The new feature would allow users to complete a medical consultation that could include blood work and medical history for personalized insights. It's the type of enhancement that its millions of users have come to expect. And it’s the type of addition that can propel Whoop to the top of a crowded space. Whoop was valued at $10.1 billion in March after a $575 million funding round. If it continues to grow through innovation and loyal users, it could see its value increase to match that of some of its biggest rivals, like Oura and Apple. CNBC dives into the new feature that Whoop is introducing this summer.

📺Prime Video’s Year-Round Sports Strategy Paying Off with Brands.

Prime Video has successfully diversified from a general streaming hub to a sports hub. Investing millions to secure media rights deals across five major sports has paid dividends in multiple ways. Prime Video attracts a younger audience than linear TV. It’s also been able to introduce new brands to the sports it partners with. Both are key drivers of sustained growth and proof that its year-round sports strategy works. In addition to its live sports offerings, Prime Video has been leaning into sports documentaries and biopics for a while. At its Upfront event to entice advertisers to buy up ad slots, it showcased “Madden”, which dives into the legendary coach and broadcaster’s life. Amazon, Netflix, YouTube, and AppleTV have all leaned heavily into sports in recent years and haven’t looked back. Prime Video has been one of the more aggressive streamers to dive into sports and show how valuable it can be for itself and its brands. Sports Business Journal describes how Prime Video has capitalized on its year-round sports strategy.

🌽College Sports Commission Wins Key NIL Arbitration in Case Brought by Nebraska Football Players.

In its battle for legitimacy, the CSC won a major battle in court. Nebraska football players were suing to allow Playfly, the school’s MMR (Multimedia Rights) partner, to secure third-party NIL agreements without needing the CSC’s input. Labeled as an associated entity, any deals Playfly can negotiate on behalf of its clients would be open to scrutiny by the CSC. This case doesn’t fully address that question, but it does influence future decisions. CSC’s battle for respect has been an uphill one and will continue to be. Its decisions regarding NIL agreements could have massive consequences. Major programs, like Nebraska, aren’t happy about it. Despite the CSC winning this case in court, some are watching to see if the school or state will sue to challenge the ruling. If they do, it would open the floodgates to complaints against its supposed overstepping of authority. The Tribune dives into the specifics of the case and why Nebraska could sue the CSC.

💰Saudi Arabia’s PIF to End Funding of LIV Golf League After this Season.

Say it ain’t so. What was supposed to be a high-powered competitor to the PGA is on the verge of collapse. It was well-known that Saudi Arabia’s PIF (Public Investment Fund) was LIV Golf’s lifeline. As of early this year, the seemingly endless pockets of the PIF had pumped at least $5.3 billion into LIV Golf. LIV Golf had been spending an average of $100 million per month on everything from player contracts to operational costs in 2024 and 2025. It doesn’t take a math wiz to know that isn’t sustainable. LIV Golf wants to somehow push through and is looking to reshuffle things to remain relevant. It’ll be a tough sell to convince new investors to take part in a venture that lost $600 million in its non-U.S. operations in 2024, but you miss 100% of the shots you don’t take. The push for new investors will be mission-critical. It could be the difference between guys like Bryson DeChambeau staying, arguably its biggest star, whose contract is expiring at the end of this season. If something doesn’t happen, he may end up going back to the PGA along with other big-name stars. CNBC informs how the end of PIF funding could decimate LIV Golf.