“Can a sports media brand's loyal audience be converted into a durable sportsbook customer base before better-capitalized operators capture the market?”
Founded in 2003 as a Boston-area print sports paper, Barstool Sports evolved into a major digital media brand under CEO Erika Ayers Badan starting in 2016. The sports betting arm — Barstool Sportsbook — launched in 2020 through a partnership with Penn National Gaming (later Penn Entertainment), which acquired a majority stake. In 2023, Penn pivoted the sportsbook brand to ESPN Bet following an ESPN partnership deal, and sold the Barstool Sports media brand back to founder Dave Portnoy for $1, effectively separating the media and sportsbook businesses. The Barstool Sportsbook as a distinct product was discontinued/rebranded.