Saturday, June 20, 2026

PENN Entertainment’s High-Stakes Gamble with ESPN Bet Kicks Off on Tuesday

  • After his Barstool failure, PENN CEO Jay Snowden has plenty riding on its 10-year, $2 billion deal with ESPN.
  • PENN currently has about 2% of the U.S.’s legalized online sports betting market.
PENN ESPN
Rafael Henrique/SOPA Images/Sipa USA, Ron Chenoy/USA TODAY Sports

On Tuesday, ESPN Bet launches in 17 states, the latest and most expensive bid for PENN Entertainment to gain traction in online sports betting.

PENN’s last attempt was costly as it took a $923 million loss from its acquisition of Barstool Sports. Over about three years, PENN’s Barstool app could only secure about 2% of the U.S. legalized online sports betting market. 

It will be several months before it will be known whether PENN CEO Jay Snowden’s latest gamble will truly allow PENN to challenge leaders like DraftKings and FanDuel. 

“I couldn’t be more pleased with the way our products and design, engineering, marketing and operations teams, ESPN and PENN, have seamlessly and tirelessly worked together to prepare us for this launch,” PENN CEO Jay Snowden said on an investor call earlier this month. 

The consensus among industry insiders is that this is Snowden’s last chance to make PENN a meaningful player in the market and possibly his last hurrah as CEO if ESPN Bet fails to gain traction. 

After the Barstool misadventure, PENN entered into this 10-year deal that pays Disney $150 million annually, roughly the same fees ESPN landed in affiliate fees with its prior betting partners, Caesars and DraftKings. Disney also was granted $500 million of warrants to purchase nearly 32 million in PENN shares as part of the deal announced in August. 

And, come Tuesday, you could look at that PENN starting from zero. While those with Barstool accounts can transfer to the ESPN Bet app, those users will have to download the new ESPN Bet app. 

Snowden warned that PENN’s interactive business anticipates “losses every quarter in 2024” as it ramps up promotions to lure bettors to the ESPN Bet app. 

“You should think about the first two years of launch to be really where those cumulative losses capsize and then in the third full year, that’s where you’d expect us to be break even or better,” Snowden said.

PENN likely will need to grab about 10% of the betting market to become profitable. FanDuel and DraftKings combined control about 70% of the market. When Caesars and BetMGM are factored in, the four companies control around 90% of the market. 

And PENN will be competing with Fanatics — which purchased PointsBet’s U.S. assets in June — is currently live in 14 states. It’s expected to rebrand the PointsBet app early next year fully, and Fanatics has vast economic resources to lure in new players.

Barstool became too polarizing for PENN to leverage, which set the stage for Dave Portney to take back the company he founded for $1. ESPN gives PENN a wider audience given its reach, which is something Snowden has talked up since the deal was announced. 

“ESPN will be implementing an initial wave of exclusive integrations across the ESPN ecosystem, which includes 200 million unique monthly users in the U.S., more than 12 million of whom are regular users of the nation’s No. 1 fantasy sports app at ESPN,” Snowden said. “Following an initial advertising campaign, headlined by Sports Center anchors Scott Van Pelt and Elle Duncan, you’ll begin to see even deeper platform and media integrations with ESPN over the coming months.”

Snowden said the combination will provide “unmatched and eventually frictionless media and betting experience.

If it doesn’t, the deal can be terminated after the third year, and Snowden’s tenure that began right before PENN purchased its first piece of Barstool in 2020 could go right along with it.

This field is for validation purposes and should be left unchanged.

Sign up for
The Memo Newsletter

Get the biggest stories and best analysis on the business of sports delivered to your inbox twice every weekday and twice on weekends.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.
Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Kalshi's logo is displayed on a smartphone placed on a reflective surface onto which a betting curve is projected in Creteil, France, on March 9, 2026, during a major scandal and a $54 million lawsuit concerning bets related to recent strikes in Iran. (Photo by Samuel Boivin/NurPhoto)NO USE FRANCE

Kalshi’s Tarek Mansour Talks Giannis, Don Jr., Supreme Court

The Kalshi cofounder discussed critics, CFTC rulemaking, and more.
Reuters FILE PHOTO: Kalshi logo appears in this illustration created on April 22, 2026.

Kalshi CEO Downplays Polymarket Rivalry

Tarek Mansour says Polymarket’s scandals risk sullying the entire industry.
Jun 13, 2026; San Antonio, Texas, USA; New York Knicks guard Jalen Brunson holds the Finals MVP trophy during the championship celebration after game five of the 2026 NBA Finals against the San Antonio Spurs at Frost Bank Center. Mandatory Credit: Geoff Burke-Imagn Images

Knicks-Spurs Draws Most-Watched NBA Finals Since 1998

The Knicks’ series-clinching Game 5 attracted 24.5 million viewers.
Soccer Football - FIFA World Cup 2026 - Group H - Spain v Cape Verde - Atlanta Stadium, Atlanta, Georgia, U.S. - June 15, 2026 Spain's Pau Cubarsi misses a chance to score REUTERS/Siphiwe Sibeko
Exclusive

Fox Frustrated by ESPN’s Lack of World Cup Coverage

Fox took over from ESPN as the World Cup rights holder in 2018.
podcast thumbnail mobile
Front Office Sports Today

A Conversation With WNBA Expansion Team Portland Fire’s GM Vanja Černivec

0:00

Featured Today

Why U.S. Open Host Sites Are on a 25-Year Plan

The U.S. Open has already picked out 22 future sites through 2051.
Wisconsin Badgers forward Laila Edwards, left, and defender Caroline Harvey celebrate after Edwards scored against the Minnesota Gophers in the first period in a game Saturday, February 8, 2025, at LaBahn Arena in Madison, Wisconsin.
June 15, 2026

Two Rookies Are Rewriting Women’s Hockey Stardom

Their platforms are a mutual boon for the PWHL and its players.
Ai sports slop
June 5, 2026

How Sports Became Ground Zero for AI Slop

The category is the perfect breeding ground for AI content churn.
FILE PHOTO: Soccer Football - FIFA World Cup - UEFA Qualifiers - Group A - Germany v Luxembourg - Rhein-Neckar-Arena, Sinsheim, Germany - October 10, 2025 Germany coach Julian Nagelsmann
June 4, 2026

‘Weird Corners of the World’: How to Find a World Cup Coach

National associations look for a winning record—and also hope for serendipity.
June 3, 2026

The Elite High Schools Hosting World Cup Teams

Spain, Morocco, Croatia, and Switzerland chose schools as their tournament base camps.

Thunder Favored, but Bettors Backing Pacers Big in NBA Finals

The most bet-on exact series outcome is the Thunder winning in five.
Fanduel
March 4, 2025

FanDuel Retains Sports Betting Crown With $14B in Revenue

The FanDuel parent company posts big increases in revenue and net income.
May 8, 2025

FanDuel Misses Projections As Betting Favorites Dominate

FanDuel is hit by customer-friendly betting outcomes during March Madness.
Sponsored

Midge Purce Sounds Off on the Trinity Rodman Rule

Midge Purce discusses the Rodman Rule and the future of NWSL.
February 20, 2025

Americans Bet $148 Billion on Sports in 2024, Up 23.6%

Both overall handle and revenue rose by more than 20% last year.
DraftKings app
February 14, 2025

Lawsuit Says DraftKings VIP Program ‘Preyed On’ Gambling Addicts

The company’s being sued for negligence and intentional infliction of emotional distress.
August 20, 2024

Beloved ‘Backyard Sports’ Brand To Relaunch After Decade Hiatus

“Backyard Baseball” was a turn-of-the-century computer hit. 
DraftKings
August 2, 2024

DraftKings Announces Consumer Tax Starting Next Year

The company’s stock fell 5% Friday morning.