Chavdar Vasilev is a journalist covering the casino and sports betting market sectors for CasinoBeats. He joined CasinoBeats in May 2025 and reports on industry-shaping stories across the US and beyond, including legislative debates, market...
Read Full BioWith the 2025 football season approaching, major operators such as Penn Entertainment and MGM Resorts along with market entrants like Kalshi and Robinhood are rolling out partnerships, product upgrades, and new offerings.
The developments highlight both the competitiveness of the regulated sportsbook market and the emergence of prediction platforms testing regulatory boundaries.
PENN Entertainment Aligns With Chicago Bears
On August 20, PENN Entertainment announced a multiyear partnership with the Chicago Bears. The agreement makes Hollywood Casino Aurora and the new Hollywood Casino Joliet the team’s official casino partners. It also names ESPN Bet as the Bears’ exclusive sportsbook partner.
The deal includes in-stadium signage at Soldier Field, digital integrations, and fan engagement initiatives. Todd George, Executive Vice President, Operations, PENN Entertainment, shared his excitement about the partnership and added:
“Teaming up with one of the premier franchises in the NFL creates exciting new omnichannel marketing opportunities for our ESPN BET and Hollywood Casino brands. Through the partnership, we look forward to engaging a large and passionate audience at Soldier Field as well as across our online products and at the new property in the Chicagoland area.”
The partnership with the Bears follows ESPN Bet’s launch of FanCenter. The operator describes FanCenter as a “personalized hub within ESPN BET that will allow customers to easily find wagering markets based on their favorite teams, players, and ESPN fantasy football rosters.”
PENN is investing heavily in the football season to uplift the struggling ESPN Bet brand. The recent deal between ESPN and the NFL can further enhance this by providing the sportsbook with increased exposure during games and coverage.
BetMGM Launches Upgraded Sportsbook App
Another gaming giant, MGM Resorts, is also looking ahead to football. Its joint venture, BetMGM, announced significant upgrades to its app. The enhancements will allow “a faster, more seamless way to build wagers, place bets, and earn rewards.”
BetMGM CEO Adam Greenblatt described the new product as the operator’s fastest and most intuitive app to date and added:
“Every detail was designed with players in mind. By blending years of customer feedback with the ingenuity of our product development team, we’ve built a premium sports betting app with a level of detail and insight that sets BetMGM apart.”
The update features streamlined navigation, a redesigned bet slip, new parlay features, and a dark theme option. BetMGM also expanded the integration with MGM Rewards. It now allows players to see points earned per wager and redeem them across the company’s resorts.
In addition, the app features betting insights from GTG Network to provide users with data on team performance and trends.
Prediction Market Developments: Kalshi & Robinhood
Outside of traditional sportsbooks, prediction markets are moving closer to mainstream football offerings.
While facing numerous legal challenges on its sports prediction markets, Kalshi recently self-certified prediction markets for point spreads, totals, and touchdown props for NFL and NCAAF games.
The move comes amid pushback from gambling regulators in some states, who argue that sports contracts are unlicensed sports betting. Kalshi maintains its markets operate under federal oversight of the Commodity Futures Trading Commission (CFTC).
Meanwhile, investing and trading platform Robinhood announced the expansion of its federally regulated event contracts to include football. Unlike Kalshi, however, Robinhood’s events will only include outcomes such as game winners and championship results.
Like Kalshi, Robinhood is engaged in legal battles over contracts. As it announced expansion into football contracts, it filed preemptive lawsuits against Nevada and New Jersey regulators, who had sent the platform cease-and-desist letters.
Separately, Kalshi and Robinhood face a lawsuit by three California Native American tribes. The plaintiffs claim the two companies violate the Indian Gaming Regulatory Act (IGRA) and threaten tribal sovereignty.
