Friday, October 23, 2026

ESPN Makes Landmark Entry Into Sports Betting With PENN Entertainment Deal

  • ESPN ends years of resistance, then reticence, with $2 billion deal.
  • Penn National sells Barstool Sports back to founder Dave Portnoy.
Man wearing ESPN logo on back of shirt while court side at mens college basketball game
Ron Chenoy-USA TODAY Sports

Want more from Front Office Sports
in your search results?

Add Front Office Sports on Google

ESPN is finally entering the legal sports betting space.

The Disney-owned sports media giant — which for years actively resisted any connection with gambling — has completed an agreement with PENN Entertainment to create ESPN Bet. 

The sportsbook, set to launch this fall in 16 states, will be a rebranding from Barstool Sportsbook, a key outlet of the sports media brand PENN purchased in two stages.

ESPN is making the move amid an ongoing and massive reorganization, including large-scale layoffs and a potential partial equity sale. But network leaders still believe the time is right, as legal sports betting further establishes itself more than five years after the landmark U.S. Supreme Court decision allowing states to set their own laws in the space.

“Our primary focus is always to serve sports fans, and we know they want both betting content and the ability to place bets with less friction from within our products,” said Jimmy Pitaro, ESPN chairman. “The strategy here is simple: to give fans what they’ve been requesting and expecting from ESPN.”

PENN Entertainment is making $1.5 billion in cash payments to ESPN over an initial 10-year term and granting about $500 million in stock warrants to purchase PENN Entertainment shares, vesting over the next decade. In return, it will access the ESPN brand and its marketing support, gaining access to the largest entity in U.S. sports digital media.

As part of the deal, Barstool Sports founder Dave Portnoy is also buying 100% of that outlet back from PENN Entertainment, ending a three-plus-year relationship that never saw the Barstool Sportsbook mount a significant challenge to industry leaders FanDuel and DraftKings. PENN Entertainment also will reap 50% of the gross proceeds of any subsequent sale or monetization of Barstool.

ESPN is making the move just days after Fox Corp. and Flutter Entertainment shuttered Fox Bet amid an ongoing consolidation in sports betting. PENN National shares shot up by more than 20% in after-hours trading amid the news that it’s dumping Barstool Sports in favor of 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

Troy Aikman

Examining Troy Aikman’s Options After J.J. Watt-CBS Deal 

Aikman has yet to receive a formal offer to return to ESPN.
Los Angeles, CA - October 27, 2025 - Dodger Stadium: Jeff Passan during game three of the 2025 World Series.

Jeff Passan: Brewers-Rays World Series Won’t Head Off MLB Lockout

Passan also addressed the backlash he received to comments about the Dodgers.

College Football’s Emerging Powers Are Shaking Up TV Ratings

BYU–Notre Dame averaged 9.2 million viewers on ABC.
podcast thumbnail mobile
Front Office Sports Today

10/22/26 – Rays-Brewers Can’t Stop Lockout, $771 to Watch NBA, Jaguars Fans’ Afterlife

0:00

Featured Today

Football - NFL - Houston Texans v Jacksonville Jaguars - Wembley Stadium, London, Britain - October 18, 2026 The necklace of a Jacksonville Jaguars fan outside the stadium before the match

Die-Hard Sports Fandom Has Reached the Afterlife

Will fans pay $6,000 to memorialize their team loyalty?
October 20, 2026

Why Europe Is Pumping Out NBA Superstars

The NBA and NCAA have an increasingly European flavor.
October 15, 2026

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?

Novig, ProphetX Told to Pause Scorigami, Micro Contract Plans

“It’s kind of a warning shot” to prediction markets, one source says.
Kalshi logo appears in this illustration taken April 22, 2026.
October 16, 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.
Polymarket logo appears in this illustration taken April 22, 2026.
October 19, 2026

Polymarket Removes Cornell 7 Market After Blowback

The market was only available on Polymarket’s international platform.
Sponsored

Blake Griffin’s Plan for Media Domination

The former NBA star is building a second act across media & entertainment.
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.
October 7, 2026

Senator Says Sportsbooks VIP Betting Inquiry Will Expand

Sen. Richard Blumenthal tells FOS he’ll look at prediction markets, too.
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.
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.
Asset Class
September 22, 2026

The Firms That Power Prediction-Market Trades

“Essentially, our role is to help bridge demand across time and space.”