Jon Gruden’s roller-coaster career began as a highly regarded, Super Bowl–winning coach. He retired, became ESPN’s highest-paid talent, returned to coaching, then resigned after the leak of emails in which he used misogynistic, racist, and anti-gay language. Gruden’s latest venture, as of Thursday: Barstool Sports personality.
It’s another sign that the independent media company, once the furthest thing from what ESPN embodied, has slowly become more like the worldwide leader in sports. And vice versa.
—Michael McCarthy
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Howard Smith-USA TODAY Sports
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When ESPN canceled the Barstool Van Talk late-night show in 2017, Barstool Sports founder Dave Portnoy predicted his rebel outfit would become the “next” ESPN. Guess what? Seven years later, he looks prescient in form if not in scale. Barstool is becoming more like ESPN—while ESPN is becoming more like Barstool.
Their parallel universes collided once again Thursday when Barstool hired former ESPN Monday Night Football analyst Jon Gruden. ESPN’s Adam Schefter reported it was a multi-year deal.
Gruden was once the highest-paid talent at ESPN, eventually earning $6.5 million a year toward the end of a stint that lasted from 2009 to 2017. Meanwhile, former Barstool host Pat McAfee is now one of the biggest stars at ESPN, hosting his own eponymous weekday show and starring on College GameDay. Like Gruden before him, McAfee is now one of ESPN’s highest-paid talents, licensing his show for $17 million per year. The 37-year-old former punter appeals to the younger audience who likes Barstool. All legacy media companies are struggling to attract younger readers and viewers. That’s why McAfee can get away with antics like prompting LSU fans to shout an obscene chant live on the air.
Lest we forget, the new ESPN Bet is essentially a rebranding of Barstool’s old sports betting platform. Penn Entertainment bought Barstool for $550 million in hopes of galvanizing its users into placing bets. It then had to sell it back to Portnoy for a song when controversy around the brand made state licensing difficult. Penn then signed a 10-year, $2 billion deal to integrate its betting platform into ESPN as an official partner.
Barstool’s Pardon My Take podcast has become a popular hangout for ESPN stars past and present, ranging from Chris Berman to Booger McFarland and Skip Bayless. With John Skipper (who canceled Barstool Van Talk) and Portnoy critic Sam Ponder gone, there doesn’t seem to be as much animosity anymore between Barstool and ESPN, with Clay Travis’s Outkick serving as chief ESPN critic and adversary.
After watching Gruden’s YouTube channel, Portnoy said he reached out to the former Raiders coach. Over dinner in Orlando, the two hit it off. Negotiations went quickly.
“I think he’s going to be an unbelievable hire for us,” said Portnoy.
Why Gruden Fits at Barstool
It helps that Gruden and Barstool share an enemy in NFL commissioner Roger Goodell. Gruden sued Goodell and the NFL, alleging the league deliberately leaked anti-gay, racist, and misogynist emails to destroy his coaching career. As Mike Florio of ProFootballTalk noted, Barstool/Portnoy occupy their own rung on the NFL’s “unofficial shit list.” Who can forget NFL security dragging Portnoy (who was wearing a Bobby Valentine–esque fake mustache to disguise himself) out of the 2019 Super Bowl?
I think Gruden still wants to coach. It’s hard to know how long he stays with Barstool. In the meantime, however, Barstool has made the biggest hire in its history. Did anybody ever think a former Monday Night Football analyst would be chopping up games with the Barstool crew?
As Barstool star PFT Commenter tweeted: “Me, coach Jon gruden, and max will be live streaming from the PMT couch commanders vs eagles for the top of the NFC East tonight. That is a sentence that would not of made any sense at all 10 years ago.”
Couldn’t agree more.
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Former ESPN personality Sage Steele is denying rumors she’s angling to become press secretary to President-elect Donald Trump.
Steele, who split with ESPN after 16 years in 2023, shot down a report by Axios she was “vying” for the high-profile job. Other more conventional contenders could include CNN contributor Scott Jennings, former Trump official Monica Crowley, Trump campaign spokeswoman Karoline Leavitt, and Trump attorney Alina Habba, according to Axios.
“Not sure how these rumors began about me ‘vying’ to be Press Secretary, but it’s definitely fake news! I haven’t had a single conversation with anyone about that job, and have no desire to do so!” Steele said.
She called supporting Trump and J.D. Vance’s campaign “the honor of a lifetime,” writing, “It took me years to not be afraid to speak up. That fear is gone forever, and I hope others are beginning to feel the same.”
During the run-up to last week’s U.S. presidential election, Steele was among the sports personalities supporting Trump, along with UFC boss Dana White, former NASCAR driver Danica Patrick and pro wrestling legend Hulk Hogan. Steele stumped for Trump on the campaign trail and moderated a town hall event with him in Lancaster, Pa., last month. Trump got her first name wrong, saying, “Let’s have a little fun, Paige.”
Steele was one of a few outspoken conservatives in her ESPN tenure, which functionally ended in 2021 after she appeared on former NFL quarterback Jay Cutler’s podcast. In the podcast, she called vaccine mandates “sick” and “scary” and criticized former President Barack Obama for identifying as Black “considering his Black dad was nowhere to be found.”
Steele apologized and was suspended for the comments. While still an employee, she sued ESPN and parent company Walt Disney Co. in April 2022, alleging they violated her First Amendment and Connecticut free speech rights. The former SportsCenter and NBA Countdown anchor left ESPN in August 2023 after settling the lawsuit. Earlier this year, she sued her longtime CAA agents, accusing them of siding with ESPN when they should have protected her interests.
The press secretary job is often a launching pad for political personalities, rather than a job for established media figures. Recent press secretaries Jen Psaki (under Joe Biden) and Dana Perino (under George W. Bush) have turned their government gigs into lucrative cable news careers.
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Mike Tyson is having his biggest media moment since The Hangover. That’s great news for Netflix as it continues its march into sports.
Friday’s fight night between the 58-year-old Tyson and 27-year-old Jake Paul is likely to shatter streaming records, considering the 283 million Netflix members who can watch it in 190 countries.
Lest we forget, Netflix is also in the NFL business, with the tech giant set to stream two games on Christmas Day, including the Super Bowl champion Chiefs vs. Steelers (Netflix has sold out its ad inventory for both games).
As my colleague Eric Fisher previously reported, Netflix will take over coverage of Raw in January via a 10-year, $5 billion deal with WWE. Look for Netflix to be a major player when UFC rights come up for grabs. If the NFL opts out of its current media deals at the end of this decade, the Big Tech trio of Netflix, Amazon Prime Video, and Google/YouTube could face off against legacy media giants Disney, Fox, and NBCUniversal for the country’s most valuable programming.
Tyson showed he could still juice interest in a big fight when he slapped Paul across the face at the weigh-in. He delivered a reality check to 13-year-old reporter “Jazzy” when she asked what tonight’s fight means to his “legacy.” The word means nothing to him, Iron Mike told the kid reporter.
“I’m gonna die and it’s gonna be over. Who cares about legacy after that? What a big ego. So I’m gonna die and I want people to think I’m this, I’m great. No, we’re nothing, we’re just dead, we’re dust. We’re absolutely nothing. Our legacy is nothing.”
Alrighty then. But give Jazzy credit. Like Maria Taylor interviewing an angry Nick Saban, she kept her composure. “Thank you so much for sharing that. That is something I have not heard before, someone saying that as an answer,” she told Tyson. Neither has anybody else on Planet Earth.
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Reaction poured in for my column this week urging Michael Strahan of Fox Sports to directly address the controversy for not putting his hand over his heart during the playing of the national anthem. The next day, Strahan did indeed post an apology on Instagram explaining he was “caught up in the moment” and simply forgot. But a majority of readers wrote that Strahan (a proud military brat whose father served in the U.S. Army for 23 years) had zero to apologize for.
Fox Sports Radio personality Doug Gottlieb posted on X/Twitter: “Since when do you have to put your hand on your heart? Stand at attention. He did. … People will have a problem with an apology. Say nothing, it goes away.”
Scott Warheit added it’s “embarrassing that Strahan—who grew up on an army base—even needed to address this nonsense. And that ‘real’ journalists took the Twitter bait and amplified it instead of calling it out for what it was. Just garbage.”
My favorite tweet, however, came from CoachB13N, who managed the two-fer of insulting both my column and beleaguered Cowboys coach Mike McCarthy (no relation): “Stick to coaching Mike. Strahan did absolutely nothing wrong.”
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- With MLB still basking in the glow of strong TV ratings for the Dodgers-Yankees World Series, ESPN will stick with what works on Opening Day of the 2025 season. The network has scheduled a doubleheader for March 27 featuring both of the 2024 pennant winners. The Bronx Bombers will play the Brewers at 3 p.m. ET, while the Dodgers take on the Tigers at 7 p.m. ET.
- NBC Sports still doesn’t have a deal to use John Tesh’s ‘Roundball Rock’ theme for its NBA game coverage starting in the 2025–2026 season, according to Alex Sherman of CNBC. Tesh is weighing whether to license the song to another media company. He could also sell the rights to a venture capital firm. “There have been some talks between the sides, which are ongoing, but Tesh is asking for a lot, and NBC Sports isn’t wedded to the theme at all costs, I’m told,” Sherman reported.
- Former ESPNer Jalen Rose is joining NBC Sports as a studio analyst for Big Ten College Countdown on the Peacock streaming platform, per Ryan Glasspiegel of the New York Post.
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Will Jon Gruden still be a Barstool Sports personality at this time next year?
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65% of you thought Michael Strahan did the right thing by getting in front of a national anthem controversy.
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