In August 2023, Penn sold Barstool back to its founder Dave Portnoy, and concurrently announced a brand licensing agreement with ESPN; the 10-year agreement is valued at $1.5 billion, plus $500,000 in options for ESPN to purchase Penn stock.

[1][2] In September 2020, Barstool and Penn subsequently launched the Barstool Sportsbook app in Pennsylvania; they sought to leverage Barstool's existing social media following and digital media properties to promote the service to a target audience of young adults, in contrast to other gaming companies that entered into marketing partnerships with sports television broadcasters (such as Fox Sports and The Stars Group, and NBC Sports and PointsBet).

[9][10] By launching an ESPN-branded sportsbook, Penn triggered escape clauses in the existing marketing agreements ESPN had with DraftKings and Caesars Entertainment for daily fantasy sports and sports betting tie-ins respectively; this resulted in the closure of ESPN's Las Vegas studio at The Linq, and ESPN2's sports betting studio show Daily Wager moving to ESPN's headquarters in Bristol, Connecticut.

[11][12][13] Ahead of the launch, the Barstool branding began to be removed from the retail sportsbooks at Penn's casinos in October 2023,[14] and Daily Wager was renamed ESPN Bet Live beginning November 10.

[15] In April 2024, the sportsbook at Hollywood Casino at Greektown was relaunched as an ESPN Bet sportsbook—marking the first retail location under the new name.