Saturday, October 17, 2026

Wall Street Sends Mixed Signals on ESPN-Penn Breakup

By ending the ESPN Bet deal early, Penn Entertainment shed itself of an expensive deal that wasn’t working. What happens next for the company is uncertain.

ESPN Bet broadcasts inside the PGA Tour Studios building in Ponte Vedra Beach, Florida, on March 14, 2025. [Clayton Freeman/Florida Times-Union]
Florida Times-Union

Want more from Front Office Sports
in your search results?

Add Front Office Sports on Google

Wall Street doesn’t know yet what to make of Penn Entertainment’s accelerated divorce from ESPN. 

The initial hours following the early Thursday announcement from the two companies to shutter the ESPN Bet sportsbook brought a whirlwind of activity, but also left plenty of questions.

Initially, investors cheered the deal, with Penn Entertainment stock shooting up about 10% in premarket trading, and then by about 5% at the opening bell. Those gains, however, were quickly erased, as by mid-morning shares were in negative territory. Penn Entertainment stock ended the day down more than 10% to $14.65 per share. ESPN parent company Disney saw its shares fall by less than 1% while stock in DraftKings, reunited with ESPN in a multiyear deal based around content and marketing, rose marginally.

The demise of ESPN Bet is an acknowledgment of the clear and, for the two companies, painful reality: ESPN Bet was stuck at a low, single-digit percentage of market share in most key states with legal sports betting, and was never going to get anywhere near the intended 20% position by 2027 as the sports duopoly of FanDuel and DraftKings remains largely intact. 

Cutting ties now allows Penn Entertainment to save hundreds of millions of dollars in fees and stock warrants to ESPN, as well as in marketing costs. The 10-year, $2 billion deal, reached in August 2023, had called for $150 million in annual cash payments from Penn Entertainment to ESPN, as well as about $500 million in warrants.

Penn Entertainment will now rebrand its U.S. sportsbook to theScore, a brand it already works with in Ontario.

“We view the ESPN Bet termination as a significant positive for Penn,” JPMorgan analysts wrote Thursday in a research note. “ESPN Bet/Penn’s expensive [online sports betting] has been a distraction for investors and management for several years (going back to Barstool) and overshadowed a fairly solid land-based business that offered an attractive pipeline of growth projects.”

Company Path

Penn Entertainment said its brick-and-mortar casinos and racetracks will indeed be a key focus going forward. Third-quarter earnings, also released Thursday, however, revealed a net loss that soared from a prior $37.5 million to $865.1 million. Revenue grew 5% to $1.7 billion, but company executives said a heightened focus on profitability will be paramount in a post-ESPN era.

“We made these digital investments to make money, to deliver a return for our shareholders. We have not done that yet,” Penn Entertainment CEO and president Jay Snowden said Thursday in an earnings call. “That’s the focus in 2026, and moving forward, to deliver profitability for our shareholders, which will only grow over time.”

In the final termination agreement, ESPN will retain vested warrants to purchase 7.96 million shares of Penn Entertainment with a weighted strike price of $28.95, a figure much closer to the company’s stock value when the deal was originally made more than two years ago. Since then, Penn Entertainment shares have fallen by more than a third. 

All other unvested and performance-based warrants, potentially worth hundreds of millions of dollars, have been forfeited by ESPN.

Download the FOS App

The business of sports, in your pocket.

QR code to download the app

Scan the QR code to get the app now.

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

NBA Draws New Lines on What Fans Can Bet On

The league is restricting risky player props.
Kalshi logo appears in this illustration taken April 22, 2026.

Who’s in Charge of the Oklahoma Tribe Doing Business With Kalshi?

Two men separately claim to lead a tribe doing business with Kalshi.
Opinion

Troy Aikman–Joe Buck Breakup Looks More Likely Than Ever

ESPN hasn’t formally offered Troy Aikman a new deal, sources say.
Nov 3, 2025; Arlington, Texas, USA; Television commentator Troy Aikman speaks before the game between the Dallas Cowboys and the Arizona Cardinals at AT&T Stadium. Mandatory Credit: Jerome Miron-Imagn Images

Aikman Eyeing ‘Next Landing Spot,’ Doesn’t Deny Rift With Buck

Aikman is slated to become a free agent after the season.
podcast thumbnail mobile
Front Office Sports Today

10/16/26 – Aikman Eyes Free Agency, CFP Nears 24 Teams, Stoudemire Becomes Cop

0:00

Featured Today

College Flag Football Is Outgrowing Its DIY Era

Women have been building the college game themselves at the club level.
Oct 5, 2026; Pittsburgh, Pennsylvania, USA; Pittsburgh Penguins general manager Kyle Dubas arrives at the arena before the Penguins host the Winnipeg Jets at PPG Paints Arena
October 12, 2026

NHL’s New Wave of GMs Is Built Different

“I am in the prediction business,” Devils GM Sunny Mehta tells FOS.
Action Images/Peter Cziborra
October 9, 2026

Is Leicester City’s $264 Million Price Tag Too Rich for Hungry Investors?

After falling from grace, how much is a former top club worth?
Oct 3, 2026; Starkville, Mississippi, USA; Alabama Crimson Tide head coach Kalen DeBoer waits to run onto the field prior to the game against the Mississippi State Bulldogs at Davis Wade Stadium at Scott Field. Mandatory Credit: Petre Thomas-Imagn Images
October 7, 2026

Who Is Alabama Football in Year 3 Under Kalen DeBoer?

The No. 6 Crimson Tide host No. 2 Georgia on Saturday.
Cubs behind the scenes
October 6, 2026

Hollywood and TikTok: Sports Media’s New ‘Blueprint’

Teams and leagues are pouring money into the quest for fans.
Cincinnati Bengal T.J. Houshmandzadeh places a $20 bet on the Cincinnati Bengals winning the Super Bowl during the FanDuel Sportsbook at Belterra Park Cincinnati Grand Opening at Belterra Park in Cincinnati.

Senator Says Sportsbooks VIP Betting Inquiry Will Expand

Sen. Richard Blumenthal tells FOS he’ll look at prediction markets, too.
U.S. President Donald Trump speaks with Commodity Futures Trading Commission (CFTC) Chairman Michael Selig in the Roosevelt Room at the White House in Washington D.C., U.S., August 19, 2026.
Exclusive
September 29, 2026

Trump Admin Preparing Crackdown on Prediction-Market Promos

The CFTC is looking at incentives like “risk-free” bets.
Sep 17, 2026; New York City, New York, USA; Philadelphia Phillies shortstop Trea Turner (7) dives safely into third base after advancing on an errant New York Mets pickoff throw to first base during the seventh inning at Citi Field. novig
Exclusive
September 30, 2026

Novig to Quadruple Valuation With New Funding Round

The company is fundraising at a $2 billion valuation.
Sponsored

The State of AI in Sports 2026

Front Office Sports and Teamworks reveal how AI is reshaping sports in the first industry-wide report on adoption, investment, and impact.
Asset Class
September 22, 2026

The Firms That Power Prediction-Market Trades

“Essentially, our role is to help bridge demand across time and space.”
Apr 1, 2026; Salt Lake City, Utah, USA; Utah Jazz forward Cody Williams (5) brings the ball up the court against the Denver Nuggets during the first quarter at Delta Center.
September 22, 2026

Ryan Smith Doesn’t Want Betting to Take Over Sports

“I think we need a little more moderation in all of it.”
Jason Robins Front Office Sports
September 15, 2026

DraftKings CEO Fires Back at Headline Calling Company ‘Struggling’

“We’re doing great,” Jason Robins said in response to the article.
First at FOS
September 15, 2026

WNBA Union Rips NBA for Exclusion From Betting Letter

Five men’s sports leagues sent a memo to regulators about betting-related harassment.