10. Erin Andrews
A sideline reporter becoming an actual, mainstream celebrity was unthinkable at the turn of the century. Then Erin Andrews came along. Andrews became a megastar on the sidelines, first for ESPN and then for Fox Sports, to this day. She weathered the storm of a horrific stalking scandal and found a way to harness her charm and personality for positive gains. Through endorsements, Dancing with the Stars, her popular podcast, and numerous other opportunities, Andrews has become one of the most well-known and well-liked sports personalities in the entire industry.
9. Pat McAfee
This might be a bit of recency bias, given Pat McAfee has only been retired from the NFL since 2017, but hardly anyone can match his meteoric rise in the industry. The former Colts punter has become one of the faces of ESPN in a short time and set the standard for navigating the contemporary media space as a television, social, and streaming star. And he’s done it all by truly maintaining his independence through a unique licensing deal with ESPN, and perhaps changing the industry for good. He commands one of the best guest lists in the industry, speaks more freely than anyone in ESPN history, has become the new star of College GameDay, and hit the jackpot as the link between the Worldwide Leader and WWE. He’ll be able to call his own shot for the next 25 years, as long he can avoid his tendency for silly mistakes and feuds that sometimes aren’t even based in reality.
8. Dave Portnoy
Through all of the ups and downs, the successes and the controversies, Barstool Sports is bigger than ever in 2025. And at each step of the way, Dave Portnoy has been the face of the movement, even after selling the company (which he bought back for $1 after selling it to Penn for $550 million). Portnoy has gone head-to-head with Roger Goodell and the NFL, courted Donald Trump, and now has a star-making television deal with FS1. It’s safe to say that the sports media industry has shifted significantly towards Barstool, especially in recent times, rather than the other way around.
7. Doris Burke
A female analyst calling a championship series in a major men’s American sports league would have sent shockwaves through the entire industry in 2000. But Doris Burke climbed that mountain in calling the NBA Finals for ESPN. Now in 2025, multiple professional men’s teams have full-time female play-by-play announcers and game analysts. And much of it is thanks to her legendary impact that will be felt for generations to come. Her time with ESPN’s top NBA team might be over, for now, but Burke still has a lot to accomplish.
6. Scott Van Pelt
Over the last 25 years, Scott Van Pelt re-invented what a sports anchor was capable of doing. He started the 2000s as your everyday Golf Channel or SportsCenter anchor, albeit with a bit more hair. In 2025, he is perhaps the most well-liked sports broadcaster in the entire country. And whether it’s doing highlights, interviews, bad beats, or anything in between, he took the show of record for sports in the United States, and made it in his image at SportsCenter with SVP.
5. Adam Schefter and Adrian Wojnarowski
There is nothing we crave more this century than information, and everyone wants to be in the know. We now have more data at our fingertips than we ever thought possible, including in sports news and reporting. The social media era has come to demand that news, trades, injuries, holdouts, and every other piece of sports information be delivered in real time. And nobody accomplished that better than Adam Schefter and Adrian Wojnarowski. They created and defined the sports insider as we know it, for better or worse. As we have discovered over the years, the life of an insider is much more challenging and often more depressing than anyone realizes, and we still don’t know if it’s all been worth it.
4. Tony Kornheiser and Michael Wilbon
The news that Michael Wilbon and Tony Kornheiser recently signed new contracts with ESPN should come as no surprise. They are the most successful sports duo in the history of sports media. When PTI launched in 2001, it was meant to bring Wilbon and Kornheiser’s Washington Post newsroom banter to television. And its beauty has always been in its simplicity – two guys, two friends, two co-workers talking about sports. Everyone has tried to duplicate it, but nobody has been able to capture the same magic that occurs every weekday at 5:30 p.m. ET on ESPN.
3. Charles Barkley
Charles Barkley is the greatest studio analyst in sports. Ever. And he has done it not through steep knowledge of Xs and Os or bold, hot takes. He has achieved this by being the single most compelling personality in sports media. You have to see what Barkley and his cohorts at Inside the NBA will do on any given night, whether it be something basketball, something serious, or something entertaining. Sir Charles is must-see TV every single night. The fact that he does it sitting at a studio desk in Atlanta makes it all the more incredible.
2. Stephen A. Smith
The rise, fall, and rise of Stephen A. Smith would make an incredible soap opera story. Smith rose first as a basketball reporter for the Philadelphia Inquirer. He was once a regular guest on The Best Damn Sports Show, Period. But by 2005, Smith’s colorful personality and ability to entertain had garnered enough attention that he was given his own show at ESPN, Quite Frankly with Stephen A. Smith. Fast-forward a few years, and Smith faded from the limelight. It looked like his best days were behind him.
But then came Act II. Smith rebuilt his career and joined First Take in 2012 as a new debate partner for Skip Bayless. The rest is history. Once Bayless left for FS1, Smith became the star of the show, and he didn’t stop there. By 2025, Smith will have built a personal brand that surpasses that of any ESPN personality in history. How many sports media personalities have ever teased a presidential run? And maybe, sorta, kinda meant it? Smith’s own personal empire includes his own podcast, his SiriusXM radio gig, a growing political career, and, you guessed it, appearances in a soap opera.
Is there anything Stephen A. Smith can’t do? We have a feeling we’ll find out one way or another over the next decade.
1. Bill Simmons
The top two in this list truly could have gone either way. However, when considering influence across all of sports media, the nod goes to Bill Simmons, as he was at the forefront of multiple movements in the sports media industry during the 2000s.
Simmons was a pioneer in sportswriting as The Sports Guy at ESPN’s Page 2, bringing the everyman fan approach to the mainstream. He did the same for podcasting through The B.S. Report. He did it again for long-form prestige sportswriting at Grantland. And was a massive driving force to the definitive series in the growing realm of sports documentaries through 30 for 30. Then, when his time with ESPN was done, he went out on his own at The Ringer, which helped pave the way for independent media ventures.
But it’s not just through Simmons’ own work where that influence has been felt; it’s through the scores of individuals who have come through the Simmons universe who have made their own marks elsewhere in the sports media industry and beyond. The Bill Simmons Coaching Tree is incredible. It’s the sports media version of the WWE Bloodline.
Every impact that Bill Simmons has had throughout sports media during the first quarter of the 2000s will still be felt in the second quarter of this century. And that’s why he’s the most influential sports media personality of the 2000s so far.
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