Get up to speed with latest news impacting the sports business landscape in Chicago and beyond. 🗞️

🗣️New Speaker Announced: Paula Hughes

Chief Digital Officer, TOGETHXR

Paula Hughes has helped transform the company into one of the fastest-growing brands in women’s sports since joining as its second employee in 2020. A former Division I rower at Syracuse University with previous digital leadership roles for the LA Clippers, Los Angeles Chargers, and Detroit Lions, Hughes has led TOGETHXR’s explosive digital growth, helping the brand surpass 3.5 million followers and become the largest women’s sports brand on TikTok. Her work has positioned TOGETHXR at the forefront of major moments in women’s sports while reshaping how fans engage with athletes and sports culture online.

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

Events include…

  • July 21st: 🎙️Panel Discussions ($399) & 🥇Startup Pitch Competition ($50)

  • July 22nd: 🚪Open Doors Chicago (Multiple Events) & 🍻Bar Survivor Competition - ($59)

  • July 23rd: 🏋️‍♀️Women’s Sports Day ($399) & 👗 Tunnel Walk Fashion Show -($300)

🗝️ All Access Pass - $699 See all the options here: https://chicagosportstechweek.com/#tickets

🚀 Chicago Startup Spotlight

🏫SeatStock is starting where fandom runs hottest: the college student section. What began as a safer, easier way for students to buy and sell student tickets is becoming a broader platform for how Gen Z experiences live events. Today, the live entertainment experience is fragmented: ticketing happens in one place, planning happens somewhere else, and the actual fan experience is left for students to piece together on their own. SeatStock brings that experience closer together through a verified, student-first ticket marketplace where students can bid, buy, and instant-sell tickets in a safer, more liquid environment built around trust and community.

The model is already proving out: in two seasons, SeatStock has grown from a one-campus pilot to 17 Power 4 campuses, reaching $1.7M in 2025 GMV, 45,000 verified users, and more than 12x year-over-year GMV growth. SeatStock is launching V3 at the end of June and expanding to 22 campuses for the 2026 football season while continuing to build toward a larger vision: becoming the fan-first home for how Gen Z discovers, plans, and transacts around live experiences. More at seatstock.com.

🏟️ Sports Business Funding & M&A — This Week

  • Women's Super League landed a record four-year U.S. broadcasting agreement with CBS Sports that could reportedly be worth up to 4x the league’s previous deal. The agreement reflects rising valuations across women’s sports properties. THE GUARDIAN

  • 🌐The VC Fast Pitch in New Orleans event, a networking and pitch competition connecting startups with investors, is expanding beyond early-stage startups to include a broader range of sports-related investments in the global sports industry as part of its June 11 program. BIZ NEW ORLEANS

  • 📈Morgan Lewis new analysis showed sovereign wealth funds and institutional investors are increasingly targeting sports IP, NIL rights, data, media, and global fan monetization instead of just team ownership. Morgan Lewis

🎟 Upcoming Local Events

🏟️SBJ Brand Innovation Summit Comes to Chicago

Sports Business Journal’s Brand Innovation Summit returns to Chicago on June 9-10, bringing together executives from leagues, teams, brands, media companies, and sports-tech firms to discuss the future of sports marketing and fan engagement. This year’s summit will focus heavily on AI in sports, women’s sports growth, NIL, creator-driven content, sponsorship innovation, and digital fan experiences.

Speakers and participating organizations include executives from MLB, WWE, TikTok, Roblox, State Farm, the Chicago Bulls, LPGA, Sephora, and Dude Perfect, highlighting how sports and entertainment brands are evolving to connect with younger audiences. Women’s sports investment and creator-athlete partnerships are expected to be major themes throughout the event.

📍Where: Chicago Marriott Downtown Magnificent Mile — Chicago, IL

📅 When: June 9-10, 2026

🆕 Club Athletic Brings Its Squad-Based Training to Chicago with Two New Locations Opening August 2026 Letting the squad down feels worse than letting yourself down. That is, according to Club Athletic and its over 2,000 members. This philosophy has spread to seven locations in lower Manhattan and will be tested in Old Town and the West Loop. Group models for fitness clubs aren’t unique. What makes this model different is that it adds the good old guilt method, which only friends and family can use well, to encourage consistency and grow membership. And where better to test the waters than in two of the more fitness-conscious neighborhoods in Chicago? Club Athletic offers various class styles, including a hybrid option, that you can mix and match based on your squad’s goals. So no excuses, or risk shame from the group chat. Fitt Insider details how Club Athletic started and what pop-up options it has available now.

🎮 Caleb Williams Becomes the First Chicago Bear to Dawn the Cover Of An NFL Franchise Video Game, Being Named the Official Madden 27 Cover Athlete Bears fans haven’t had much to be proud of at the Quarterback position in the past, but this year, they finally get to see one of their own represent the cover of Madden 27. EA Sports announced on Wednesday morning that the former Heisman winning QB would be the face of this years game, representing the Standard Edition, as well as the Deluxe Edition cover. The Standard Edition shows Williams doing his iconic jump-man throw with the Chicago skyline in the background, giving flashbacks to MJ, and the Deluxe Edition brings out the Iceman himself in the icy-white road jerseys, with snowflakes falling all around him. Williams is rated a 90 overall in the game despite being on the cover, and Bears fans everywhere will cross their fingers that this number rises by the end of the year, and denies all potential for a “Madden curse” year. Checkout Bleacher Report for more details.

🏷️ Bulls Championship Banner, Michael Jordan Rookie Jersey are Up For Auction The 92-93 Bulls are never picked as the best team of the first 3-peat, but now they’ll get to stake their claim of value among collectors. The championship banner from the ‘93 NBA title is one of the last pieces of memorabilia to hang in the legendary Madhouse on Madison. So despite the 91-92 Bulls holding the crown as the best of the 3-peat, it’s that ‘last of an era’ distinction that could fetch the 92-93 Bulls championship banner big money. Jordan’s rookie jersey also has a similar level of rarity that adds to its appeal. Rated a 9+ by PM&G, the jersey has yellowed spots from his sweat and a mark where the shorts fell. Can’t get more authentic than that. Serious collectors would drool at the prospect of owning invaluable pieces of Bulls history. The Sun Times mentions when the auction ends and other key details.

🏦 Hawthorne Race Course Alleges Illinois Official Steered Funds to Rival Track Amid Bankruptcy Battle If Hawthorne Race Course does eventually fold (and it’s not looking good), at least it can say it went out swinging. If the allegations are true, it could at least slow the bleeding as it stares down bankruptcy. Hawthorne owes more than 200 creditors over $100 million. It also failed to capitalize on an opportunity to convert into a ‘racino’, a racetrack and casino combo, despite legal authorization to do so. It was still receiving more in grant funds from the Illinois Dept of Agriculture (IDOA) than its chief competitor, Fairmount Park, but saw its share dwindle. According to Hawthorne representatives, Fairmount hadn’t changed its operations to justify its larger share of grant funds. In reality, Hawthorne’s allegations against Fairmount are worth pennies compared to what it owes, and probably won’t prevent bankruptcy. But any kind of small win helps during the demoralizing bankruptcy-filing process. The Tribune covers the full scope of the accusations, who was involved, and how much Hawthorne was receiving from the IDOA.

🛼 Garfield Park Roller Rink And Park Get $2 Million Overhaul With New Play Space, Event Stage This year, Juneteenth marks a new era for a community looking for a refresh. Once a vibrant hub of commercial commerce, the site of the new roller rink sat vacant for decades. It was a reflection of the state of the greater West Side. Thanks to calls for renewal and restoration led by West Side residents and groups, the overhaul is part of a broader plan to restore some of the area's glory after so much disinvestment. The roller rink features a nature play area, murals, and an event stage for resident enjoyment. Its vibrant colors and inviting structure can reshape the image of a blighted spot on W. Madison St. for as long as many can remember. Block Club Chicago shares the images and goals of the vital people involved in the project.

💊 A New Sporting Event's Controversial Pitch: Performance-Enhancing Drugs Welcome Of course, Las Vegas would be the city hosting a controversial, groundbreaking new event. At the heart of the controversy is whether condoning doping in sports ever makes sense. For purists, the answer is an obvious no. But when diving in a little deeper, it’s not so black and white. Enhanced Games paid the winners of each event $250,000, many magnitudes more than Olympic athletes earn for winning gold for their countries. There are also no requirements that all athletes must take performance-enhancing drugs. Enhanced Games even promised a million-dollar prize for any new world records, obviously life-changing money for many. It is especially enticing for athletes who train and put their bodies on the line, in some cases, for less than minimum wage. Unfortunately for Enhanced Games (especially after securing over $32 million in sponsorship contracts), its share price dropped sharply following what was viewed as an underwhelming debut. But if it continues and meets investor/spectator expectations, it could open up more dialogue about allowing PE drugs in sports. NBC 5 captures the opinions on both sides after the debut of the Enhanced Games.

🎖️ How Fanatics Cornered the Sports Collectibles Market Since Michael Rubin took over Fanatics in 2011, the company has become the dominant presence in sports culture. It went from just a small sports collectibles company to a global enterprise with multiple verticals and $14 billion in annual revenue. Having secured licenses with the NFL, NBA, and MLB, it can now count the FIFA World Cup as a partner in its efforts to dictate the sports collectibles market. Its newest deal will add debut patches to World Cup debutants that’ll be removed and added to a future sports card. Great for Fanatics, terrible for its competitors. Panini, in particular, accuses Fanatics of aiming to monopolize the industry. While possibly true, Panini has had its own issues to deal with and has little leg to stand on. It faced a lawsuit in 2019 from customers regarding unfulfilled requests. In its eyes, Fanatics doesn’t see Panini posing much of a threat in its continued ascension. CNBC dives deep into the Fanatics vs Panini beef.

💸 Browns Will Sell Three Percent of Team to the Arctos Private-Equity Fund Winning on the field and off the field have completely different meanings. Arctos Partners, now with stakes in three competing AFC teams, cares less about the wins on the field than the almost guaranteed wins off of it. It became the first private equity firm to invest in multiple NFL teams after buying into the Bills in late 2024 and adding the Chargers last year. By adding a third team in the Browns, Arctos can bank on growing the value of its combined stakes thanks to the NFL’s perpetual money machine model. NFL franchises have outpaced the S&P 500, compounded annually, over the last few decades (11.3% for NFL franchises vs 7.6% for the S&P 500 from 1991-2020). Arctos knows it can bank on the league's value increasing by the time it wants to cash out its stakes, especially as the NFL pushes international expansion. If there’s such a thing as a recession-proof stock, the NFL is as close as it gets. Arctos has been the biggest player among PE firms to capitalize on that so far. NBC Sports reports on the Browns' sale of a minority stake to Arctos.

⚽️ MLS Partnership Shows How AI Could Shape Sports Fandom It may trail Europe and South America in viewership today, but the MLS is investing heavily in personalized, AI-driven technology to connect to its fans better and drive more viewership tomorrow. World Wide Technology (WWT) is the league’s new technology partner and promises to enhance fan engagement, content personalization, and match-day experience. WWT has worked in diverse industries, including healthcare, energy, and manufacturing, bringing insight into how to apply its expertise to the world of sports. Sports used to mainly compete against each other for attention. In today’s attention-driven economy, sports are competing with everything a fan has access to on their phone. The MLS understands this better than most leagues. It has continued to make a concerted effort to build systems that satisfy its fans, even as social media, fantasy sports, gaming, etc., compete simultaneously. Forbes summarizes the new partnership and its potential impact on MLS fans.

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