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Outsider Hires Deirdre Lester Away From Barstool Sports

The lifestyle brand was founded by Shannon Terry and Jay Cutler. ESPN’s Marty Smith is also a partner.

Jordan Bondurant

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Former NFL quarterback Jay Cutler has called on a former Barstool Sports executive to help lead his new media brand.

Deirdre Lester is set to become the CEO of Outsider, a lifestyle company focused on sports culture. She was the chief revenue officer for Barstool and helped that company expand to over $200 million in revenue.

Cutler co-founded Outsider with entrepreneur Shannon Terry in 2020. The Nashville-based company employs more than 50 people full-time and continues to secure capital funding.

Lester told Front Office Sports the brand already has some podcasts in the can, including one hosted by ESPN’s Marty Smith (also a partner in Outsider), with plans to offer more unique content tailored to their specific audience.

“We will be producing more content shows that really speak to a variety of different areas of American entertainment and American culture that we feel have a theme of commonality – and embrace that Outsider mindset,” she told Front Office Sports’ Michael McCarthy.

Right now, the focus of content will be on NASCAR and country music, areas Lester says are key interests for their audience.

“We’re going deep on NASCAR in a way that a lot of the other sports media companies don’t,” she said. The company will also develop content centered on the outdoors.

Cutler will have a presence behind the microphone and in front of the camera, Terry said.

“He’s a one-liner extraordinaire. He’s really funny, and he’s interesting. At the end of the day, he’s memorable,” Terry said. “You may like him or you may dislike him, but he’s memorable. So he’s definitely going to help us on the media side.”

Sports Online

Mike Francesa: George Steinbrenner’s Idea to Put Mike and The Mad Dog On YES Network

“It was George’s idea. So give him credit for it. He wanted Mike and The Mad Dog as part of the CBS Radio contract, and we were.”

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Mike and The Mad Dog is often cited as one of, if not the, best sports radio shows of all time. The show saw an expanded reach with its partnership with the YES Network beginning in 2002. During his podcast Tuesday, Mike Francesa gave all the credit to the simulcast hitting the air on YES Network to the late Yankees owner George Steinbrenner.

“It was George Steinbrenner that came up with the idea of Mike and The Mad Dog being on the YES Network. No one else,” Francesa said.

“They came to us when they were negotiating a new radio deal with him and they said ‘Hey, we need a quick answer on this. Would you guys want to be on the YES Network every day, simulcasting? You know what Imus is doing with MSNBC? We wanna do it with you guys, but we need a very quick answer’.”

Francesa said the show airing on YES Network was a sticking point for the Yankees in negotiations with CBS Radio to continue airing the franchise’s broadcasts.

“Our first deal with them were not for a lot of money. Our later deals with them were for a very significant amount of money. But it was George’s idea. So give him credit for it. He wanted Mike and The Mad Dog as part of the CBS Radio contract, and we were. Our joining the YES Network was part of the CBS Radio contract.”

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Sports Online

Dave Portnoy Reveals Back-And-Forth With New York Times Reporter Who Claimed He ‘Did Not Provide Answers’

“You waited till (sic) your hit piece was done and now you just need to say you gave me a fair chance to speak even though you have no interest in the truth and your article is already written”.

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A story from The New York Times centered around “aging casino company” — Penn National Gaming — and its relationship with “degenerate gambler” — Barstool Sports founder Dave Portnoy — caught the eye of the face of the online outlet after the claim that he “didn’t provide answers”.

In the story, Steel claims “Penn and Barstool executives did not respond to repeated messages. Mr. Portnoy did not provide answers.” Portnoy brought the receipts to Twitter with a video of all of the correspondence he had with Times writer Emily Steel.

The alleged conversation takes place sporadically from May through November, with Portnoy offering to meet face-to-face with Steel for an interview that is mutually audio and video recorded, which Steel declines. She offered to meet Portnoy in New York for an audio recorded interview, which he declined, saying the interview needed to take place in Miami, because “I’m not running around to accommodate you at the 11th hour.”

He added “You waited till (sic) your hit piece was done and now you just need to say you gave me a fair chance to speak even though you have no interest in the truth and your article is already written”.

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Sports Online

Kareem Daniel Leaving Disney After Bob Iger Reassumes Role as Company CEO

“This is a time of enormous change and challenges in our industry, and our work will also focus on creating a more efficient and cost-effective structure.”

Jordan Bondurant

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Bob Iger is back as the CEO of Disney, and one of the first moves he made was to announce a company restructure. Part of that restructure includes the departure of Kareem Daniel, the chair of Disney Media and Entertainment Distribution (DMED).

DMED was formed under now-previous CEO Bob Chapek. The division manages Disney’s streaming services which includes ESPN+.

Daniel was considered one of those closest to Chapek. Iger announced Daniel’s departure in a memo to employees at DMED.

“It is my intention to restructure things in a way that honors and respects creativity as the heart and soul of who we are,” Iger said in the memo. “As you know, this is a time of enormous change and challenges in our industry, and our work will also focus on creating a more efficient and cost-effective structure.”

ESPN president Jimmy Pitaro will join other company leaders in coming up with a new company structure that Iger hopes “puts more decision-making back in the hands of our creative teams and rationalizes costs.”

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