Saturday, September 5, 2026
The FOS App is Live Download It Now

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

Opinion

Winners and Losers of NBA’s Stiff Clippers Ruling

The punishments have sent shock waves around sports media.
Sep 30, 2024; Inglewood, CA, USA; Los Angeles Clippers forward Kawhi Leonard (2) talks with team owner Steve Ballmer during media day at Intuit Dome. Mandatory Credit: Jayne Kamin-Oncea-Imagn Images

Clippers Punishment Puts Disputed ESPN Report Under Spotlight

An NBA spokesperson previously called the ESPN report inaccurate.

Prediction Markets Arrive on Supreme Court’s Doorstep

New Jersey asked the Supreme Court to weigh in.
First at FOS

Massachusetts Reviewing Bill Simmons’s Proxy Betting Admission

Simmons said he had his daughter’s boyfriend place bets for him.
podcast thumbnail mobile
Front Office Sports Today

9/4/26 – Judge Clears Pros for College, Good Good CEO Out, Russini Plots Comeback

0:00

Featured Today

Wild Transfer Window Shows How Premier League Towers Over Soccer

Spending in England vastly outstripped the rest of Europe.
September 3, 2026

Teams Are Spending Millions to Build Luxury Locker Rooms

It’s a recruiting pitch, a retention tool, and a seven-figure line item.
September 1, 2026

High School Football Sidelines Are Clogged With Content Creators

Administrators call these amateur newcomers the “pajama paparazzi.”
Aug 3, 2026; Washington, D.C., USA; Alexandra Eala (PHI) kisses the championship trophy during the trophy ceremony after her match against Jessica Pegula (USA) (not pictured) in the women's singles final of the 2026 Mubadala DC Open at Rock Creek Park Tennis Center. Mandatory Credit: Geoff Burke-Imagn Images
August 30, 2026

How Alex Eala Turned the Philippines Into a Tennis Nation

A December homecoming match could break tennis’s attendance record.
August 26, 2026

Deshaun Watson Has Done the Impossible: Unite Browns Fans

Watson was named the starter after complaining boos were “personal.”

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

Kerri Walsh Jennings’s Playbook for the Future of Volleyball

The former gold medalist talks NCAA, the Olympics, & investing in volleyball.
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.