Sunday, May 24, 2026

ESPN, PENN Entertainment Looking To Break Sports Betting’s Duopoly

  • FanDuel, DraftKings currently hold a combined market share of more than 70%
  • Depth of ESPN’s efforts at user conversion will heavily influence ultimate success of deal
Disney
Ron Chenoy-USA TODAY Sports

ESPN’s $2 billion deal with PENN Entertainment to create ESPN Bet represents a massive bet on its ability to break what has quickly become a U.S. sports betting duopoly between FanDuel and DraftKings.

In the five years since the U.S. Supreme Court allowed individual states to set their own sports betting rules, FanDuel and DraftKings have used large marketing spends and their existing presence in fantasy sports to collectively control more than 70% of the domestic online sports wagering market. Including Caesars and BetMGM, the combined market share reaches about 90%, leaving any other operator competing for scraps.

Even as key new states such as New York have entered the market over the past two years, FanDuel and DraftKings quickly established the same level of market dominance, helping lead to the demise of a growing series of former challengers including MaximBet, Fubo Sportsbook, Churchill Downs, theScore, and most recently, Fox Bet.

“Best case, at least in the short term, is ESPN and PENN getting on the podium,” into third place, Dustin Gouker, a sports betting consultant and longtime gaming journalist, told Front Office Sports. “PENN clearly calculated there was far greater upside in this deal than staying with Barstool, and they may have already hit a ceiling with Barstool. So PENN is clearly saying ESPN is the bigger brand, which it obviously is, and that they can go further now.”

Exactly how much further rests in large part on how aggressively ESPN puts its marketing muscle behind the pact. The PENN Entertainment deal specifically calls for high levels of content integration for ESPN Bet within ESPN’s ecosystem and access to network talent.

But the forthcoming NFL season — set to be a major sports betting event and roughly coinciding with the fall debut of ESPN Bet — will serve as a critical indicator on the depth of ESPN’s intentions with this deal.

“What I’m looking to see is how motivated ESPN really is in helping to convert users,” Gouker said. “If they really get behind this, there’s certainly room for growth.”

That growth, however, could be additionally challenged by not only the established incumbents, but by Fanatics, newly buttressed with its $225 million purchase of PointsBet’s U.S. operations.

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

Big Money on the Line on Premier League’s Final Day

Arsenal has won the title, but millions are still at stake.
Texas State mascot

Mascot-Reveal Videos Are the Newest College Sports Tradition

Student mascot unmasking videos are going mega-viral.
Charlie Pliner and Nikolas Rohrmann

How 2 Brown Undergrads Became Sports Dealmakers

An experimental project turned into a permanent course and business deal network.
U.S. Senator Richard Blumenthal (D-CT) speaks with the press after the Republican-controlled U.S. House of Representatives passed bipartisan legislation to fund Department of Homeland Security agencies including the Secret Service and Transportation Security Administration in a move to end the partial shutdown that has gripped their operations for nearly 11 weeks, on Capitol Hill in Washington, D.C., U.S., April 30, 2026.

Critics Warn Kalshi and Polymarket Risk a Juul-Style Reckoning

Their advertising methods came under fire from lawmakers this week.

Featured Today

NFL Rivalries Are Made on the Field, Mocked in Schedule Release Videos

Every year, teams find new ways to one-up themselves (and their rivals).
Bart Swings/Falyn Fonoimoana/Avery Poppinga
May 14, 2026

OnlyFans Is Paying Pro Athletes What Their Sports Won’t

The adult-content platform is a reliable income source for niche athletes.
May 13, 2026

How Sports Graphic Designers Are Grappling With the Rise of AI Art

The release of ChatGPT 2.0 Images sparked a conversation among sports designers.
May 12, 2026

Collectible Cups Are Sending Sports Fans Into a Frenzy

The drink is secondary to the wild vessel it comes in.
Mark Cuban

Mark Cuban: ‘Betting Isn’t the Problem’

These wagers have been behind the recent MLB and NBA gambling scandals.
DraftKingsApp
May 18, 2026

DraftKings Cofounder: Kalshi Is Years Away From Competitive Product

Kalshi responded with a gif from the movie “Mean Girls.”
Jun 12, 2025; Washington, DC, USA; Gov. Tim Walz (D-MN), left, alongside Gov. JB Pritzker (D-IL), right, and Gov. Kathy Hochul (D-NY), not shown, testify before the House Committee on Oversight and Government Reform during a hearing on state immigration enforcement policy in Washington, D.C., on June 12, 2025.
May 19, 2026

Trump Admin Sues Minnesota to Block Prediction-Market Ban

Minnesota is the sixth state the federal regulator has sued.
Sponsored

How Microsoft and the Premier League Are Making Fans Feel Closer to the Game

The Premier League reaches fans in 189 countries. Now, with Microsoft, it is making global fandom more personal through AI.
May 9, 2024; Columbus, OH, USA; Sports are shown on TVs behind the bar as guests enjoy the grand opening of DraftKings Sports & Social in the Short North. Though there are no on-site betting windows, eligible customers can place bets through the DraftKings app.
May 15, 2026

Gambling Layoffs Pile Up As Sports Betting Industry Recalibrates

Penn Entertainment headlines three companies with layoffs this week.
exclusive
May 14, 2026

Polymarket’s Soccer Spree Continues With Serie A Deal

It’s the third big soccer deal Polymarket has reached this year.
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
May 13, 2026

N.M. Tribes Claim Kalshi Sports Markets Violate Federal Law

The suit cites the same law a Wisconsin judge said tribes can pursue claims over.
May 8, 2026

DraftKings, FanDuel Push Further Into Prediction Markets

“It’s one of our fastest to profitability business lines we’ve ever launched.”