ESPN's failed bet says everything about sports gambling in 2025

Tech Insider : Sports, Sports, Business
A football game between the Atlanta Falcons and the Buffalo Bills on October 13, 2025
A new deal means sports bettors who watch ESPN broadcasts - like October's Monday Night Football matchup between the Atlanta Falcons and the Buffalo Bills — will be directed to DraftKings, and not the "ESPN Bet" brand the company had created with Penn Entertainment.

David J. Griffin/Icon Sportswire via Getty Images

Jimmy Pitaro breaks down ESPN's streaming gamble — and why it took so long

Tech Insider : Sports, Business, Technology
ESPN head Jimmy Pitaro speaks onstage at a company event, 2018
ESPN boss Jimmy Pitaro wants you to start streaming his service - unless you already have a cable TV subscription.

Meg Oliphant/Getty Images

ESPN Bet has big ambitions and a tough outlook as it launches in New York and aims to gain share in sports betting

Tech Insider : Sports
A hand holds a smartphone displaying the ESPN logo, against a blue stock market background.
Betting is an increasingly big part of ESPN's growth strategy, its executives have said.

Budrul Chukrut/SOPA Images/LightRocket via Getty Images

Subscribe to penn-entertainment