ESPN is officially getting into the sports betting game — in partnership with Penn Entertainment (NASDAQ:PENN) — who just landed what may be the most important sports betting deal in history.

How important is ESPN in sports betting? Enough to send competitor DraftKings (NASDAQ:DKNG) down over 10% and Penn up nearly 9% yesterday.

It’s been a long-anticipated move by ESPN — the largest US sports media brand — as ESPN’s majority owner Disney had been hesitant about entering sports betting for years. Under the agreement:

• Penn will pay $1.5B to ESPN over ten years.
• Penn will rebrand its Barstool Sportsbook to ESPN Bet.
• ESPN will promote the app across its platforms and talent.

Penn will also sell 100% of Barstool back to its founder Dave Portnoy — who sold Barstool to Penn starting in 2020 over two transactions — and is repurchasing it for what could be pennies on the dollar.

The fallout between Barstool and Penn

Penn, founded as a racetrack and casino operator, had banked on the Barstool brand to break into online sports betting.

• In 2020, Penn began acquiring Barstool, hoping to leverage its brand to compete against dominant industry giants DraftKings and FanDuel.
• But three years later, the Barstool Sportsbook app had failed to meet expectations — and Barstool’s lawless way of operating may have led to them being denied state gambling licenses, per Portnoy.

Investors have criticized money-burning sports betting apps for their massive losses — after years of pumping billions into lavish campaigns to acquire a single user for thousands of dollars.

With the ESPN partnership, Penn will gain access to hundreds of millions of people — but it still needs a lot of work to get rid of its “second/third-tier sportsbook” image given by media analyst Rich Greenfield.