An Inside Look at Sports Media: ESPN Radio, Monday Night Football, Expiring Contracts, & More

Over two months ago, I made the decision to join Outkick the Coverage. A website I've long read and I'm thrilled to now call it my home. With that said, I've been off work, during my transition, for about six weeks. During that time, ironically, the beat I primarily cover, sports media, rapidly churned out news and talking points. Stories that needed more than 280 characters to address. I thought there would be no better way to introduce myself to the Outkick audience than by providing both my thoughts and what I'm hearing on the industry's top ongoing stories:

Monday Night Football, anyone?

It's May 1, and the uncertainty surrounding the Monday Night Football booth remains the biggest story in sports media. The year-long plan to poach Tony Romo failed. Plan B, also known as the Annual Peyton Manning Pitch, ended the same way. ESPN took a swing at Drew Brees for its future, as first reported by Outkick, but according to the New York Post, Brees chose NBC. So, what now?

Clearly, in its attempt to fix its heavily-criticized booth, ESPN has had its sights set on marquee names. Names that cause nostalgia. Names that make you remember the kind of beer you drank when they threw a game-winning touchdown pass. Former players you still picture wearing a certain jersey and number. All of the perks that come with Manning, Romo, and Brees. There aren't many of them hanging out looking for jobs.

If decision-makers remain adamant this is what they want, Kurt Warner is the best remaining option. Warner, in addition to his name recognition, has impressed in the booth for the NFL Network.

In-house options Louis Riddick and Dan Orlovsky are, however, the names that come up most frequently, talking to industry sources. Sometimes together in a potential three-person booth. Neither were household names during their playing careers but are both fixtures and acclaimed analysts on ESPN's programming. The network is high on Orlovsky seeing him as a key ingredient to its current and future programming. Riddick's name has floated around for this job for the past several years and once again had a presence during the draft.

Picking Riddick and/or Orlovsky would give ESPN's NFL coverage synergy as both would presumably remain featured on the daily studio shows. This would give the brand an identity, which it's been lacking for years.

Joe Tessitore has received a larger share of the blame for the past two years than he was responsible for. Particularly, in the second half of last season when the critics appeared done with the entire in-game coverage. Though, Steve Levy is looked at as the internal front-runner to call Monday Night Football.

Regardless of who Monday Night Football's play-by-play commentator is this upcoming season, ESPN should aggressively make a push for Ian Eagle next year when his deal expires. Eagle is a top-level NFL game-caller and is just as good at calling basketball. Eagle would give ESPN that versatile, big-moment play-by-player it lost with Mike Tirico's departure.

The big picture ramification of this continuing process is the paradigm-shifting status of high-level game analysts. Stephen A. Smith came into 2020 as the most powerful talent in the business. That is now Tony Romo thanks to an unprecedented bidding war between ESPN and CBS that crossed over into mainstream sports talk shows. If Manning would've made the leap to broadcasting, he would've been right up there, as well. The past few months have painted a clear picture of the shortage of A-level NFL color commentators. This will undoubtedly bode well for Troy Aikman and Cris Collinsworth when their contracts are up. It could also speed up the retirements of current players who have star potential as game analysts.

ESPN Radio overhaul

I've said it a few times, the second-biggest, up-in-the-air story in sports media is ESPN Radio. Changes to the radio lineup have been discussed over the past weeks and months, sources say. The morning show, due to the key markets that carry it, is the most impactful domino to fall. While at The Big Lead, Outkick's Ryan Glasspiegel and I reported Trey Wingo wants off Golic & Wingo. Wingo could have interest in a show later in the radio lineup, sources have recently said.

There is industry-wide speculation the Dan Le Batard Show's time on radio could be winding down; the New York Post was first to report this. On Wednesday, Le Batard said on-air executives denied this was true.

First Take, Your Take has always felt more temporary than permanent. To no fault of the host Jason Fitz, who is a talented broadcaster and can carry his own show somewhere in the lineup.

Max Kellerman is the most noteworthy name to keep an eye on with such valuable real estate expected to be available. The 6-10 a.m. ET slot needs a big-name, polished broadcaster to front it. Kellerman could find fronting a new revamped morning radio show more appealing than sharing First Take with Stephen A. Smith, who his chemistry with isn't ideal. Sources mention Keyshawn Johnson as a possible co-host if Kellerman were to make a move to radio.

Emmanuel Acho was also discussed as a possibility for radio, per sources.

Jorge Sedano, Peter Rosenberg, and Chris Carlin are three local hosts who could bolster the national lineup in the afternoon.

John Buccigross would be a good fit for the lineup if the network were to look for a wild card. While he doesn't have a radio background, Buccigross, with his fun, relatable personality, would immediately connect with sports fans across the country. The popular SportsCenter host has shown the underrated ability to develop a quick rapport with various co-hosts and interviewees.

Expiring media contracts

Decision 1.0 for Tony Romo didn't quite reach LeBron James and Tom Brady level, though it often felt close. With Romo off the board, here are some notable sports personalities with contracts set to expire between now and the end of the year:

Media winner of the NFL Draft

We can argue over the next few weeks which NFL team had the best draft. The Bengals think they found their franchise quarterback. Dallas stole CeeDee Lamb. The Ravens managed to grab players with ridiculous value. Kansas City added an instant game-breaker who was born to play for Andy Reid in Clyde Edwards-Helaire. Maybe you think your team won the draft (no, I don't think my Lions did). These same debates are not taking place in media circles. Daniel Jeremiah from the NFL Network was the clear winner.

Jeremiah was introduced to many new sets of eyes appearing on both ESPN and NFL Network as they simulcasted the draft this year due to pandemic limitations. The latter of the two networks is watched by far fewer viewers. Jeremiah was quick on his feet, informative, energetic, and his knowledge somehow seemed to ascend as the draft reached the later rounds.

The former scout made all of us smarter — as much as one can be made —  for three-straight days with in-depth and insightful nuggets. He wasn't thrown into an easy position, either. While his colleagues, Warner and Michael Irvin, were just split-screens away, Jeremiah spent most of his airtime with Mel Kiper and Trey Wingo, two ESPNers who have years of chemistry built up.

Nonetheless, the highlight of his applauded outing had nothing to do with football. It was his heartfelt thank you to Chris Mortensen.

Kiper and Todd McShay, who we wish the best to while recovering from the coronavirus, are phenomenal — but there is now a third name in the equation of must-follows during draft season. It would hardly be surprising to see and hear more of Jeremiah moving forward.

Selfishly, let's hope, from a media perspective, Jeremiah doesn't leave the business for a front-office role, as some have suggested.

The end of an era in boxing coverage

I reported in April, ESPN did not to renew Dan Rafael's contract. Rafael spent nearly two decades with the network as one of the industry's most-noted boxing writers. This decision leaves a glaring hole in ESPN's coverage. ESPN has gone all-in on boxing since reaching an eye-opening seven-year deal with Top Rank in 2018. Top Rank's coverage is top of the line with Max Kellerman, Joe Tessitore, Mark Kriegel, and Andre Ward. But it lacks a news-breaker, a position ESPN routinely has hired away from the competition. This most notably includes Adam Schefter and Adrian Wojnarowski. ESPN brought in Jeff Passan and Ariel Helwani over the past few years to strengthen its coverage of their respective sports, MLB and MMA.

It's hard not to point to The Athletic's Mike Coppinger. His stock has risen exponentially in the past year as boxing's top news-breaker. Coppinger could be used like Passan at ESPN, where MLB and boxing are covered about equally.

Coppinger made waves beyond up-to-minute transactions in the fall with an inside look at the fractured relationship between Canelo Alvarez and his promoter, Oscar De La Hoya. The piece recently won Coppinger a Boxing Writers Association of America award in the Investigative Reporting category.

Behind-the-scenes media moves.

Maxx Sports & Entertainment Group, the talent agency led by Mark Lepselter, has made moves all throughout the pandemic. Shaun Wyman joined the company as an agent from ESPN, where he spent 19 years. Wyman most recently held the title of director of talent planning and negotiations. Maxx recently added ESPN's Bobby Carpenter, ESPN/Thirty Five Ventures Rosalyn Gold-Onwude, SEC Network's Alyssa Lang, Barstool's Trysta Krick, and NFL Network's Marc Ross to its list of clients.

"We are very happy to have Shaun join Maxx Sports and Entertainment. His nearly 20 years of experience at ESPN, in a variety of roles, is a tremendously valuable addition to the firm," Lepselter tells Outkick. "Like everyone else, we have collectively tried to be as productive as possible. Stay creative, do some internal housekeeping, and most importantly stay in close contact with all of our clients."

The agency's clientele includes Nate Burleson, Rodney Harrison, CC Sabathia, Melanie Collins, Chris Haynes, Brandon Tierney, and Bart Scott.

NBA insider Haynes recently reached a two-year extension with Yahoo! Sports.

Some other thoughts.

I. I expected high viewership for The Last Dance. And, uh, yeah, "high" doesn't cut it. The viewership through the first four episodes is astounding. The doc is averaging an unheard of 6 million viewers per episode. I'd expect it to dip some moving forward because that's how this stuff works. But this is Michael Jordan, not LeBron James (kidding, it's Friday).

II. One thing that has bummed me out is seeing so many people on Twitter binging various television series. I have not been able to find one worth it. Maybe I've seen all the good ones — I don't know. Instead, I started and finished five books in the past four weeks. Stephen King's "The Institute;" the thrilling true-crime novel by Michelle McNamara, "I'll Be Gone in the Dark;" and three from Harlan Coben: "The Boy from the Woods," "Tell No One," and "The Woods." All five are highly recommended. As for why three are from the same author – I'm convinced anything Coben writes should be adapted into an HBO series, instantly.

III. While I couldn't find anything to binge, I did catch each week — I know, how 2012 — of Better Call Saul's penultimate season. I don't care if this sounds prisoner of the moment: it was the best season of television in years. To avoid spoilers, I'll just say Vince Gilligan and Peter Gould are one season away from a masterpiece.

IV. There will officially be an oversaturation of streaming services by mid-July. HBO Max (May 27) and NBC's Peacock (July 15) will soon join the crowded space with Netflix, Hulu, Amazon Prime Video, Disney Plus, Crackle, CBS All Access, and whatever else is available. It's hard to see any service catching Netflix in the near future, or ever. Even as the others have and will pull from the steaming giant's library, Netflix remains irreplaceable for most streamers. It has even surpassed HBO as the leader of best original content after a blockbuster 12-month period, which included Stranger Things 3, The Irishman, The Witcher,Ozark, and Tiger King.

V. Social media can be a demoralizing, off-putting place. Though, it certainly has its perks. Such as when a picture goes viral and hilarious memes follow. Thank you, Michael Jordan. Again. Oh, and Bill Belichick's dog.

VI. Yes, we are all still waiting for "The Winds of Winter."

Disclosure: Outkick’s founder Clay Travis is an on-air talent at FS1.

Written by
Bobby Burack is a writer for OutKick where he reports and analyzes the latest topics in media, culture, sports, and politics.. Burack has become a prominent voice in media and has been featured on several shows across OutKick and industry related podcasts and radio stations.