In my estimation, the sea change began in 2015. Bill Simmons and Colin Cowherd exited ESPN within months of each other. For different reasons, both had fractious splits with the Mothership. Amidst doubts from some in the industry as to whether they’d remain relevant or disappear, they leveraged personal audiences that platforms like Twitter, Instagram, and YouTube had suddenly made portable to prove that prosperity was attainable outside ESPN. Not only that, they stayed relevant in the conversation. Six years later, as content has continued to fragment and the gambling behemoths have entered the chat, the paradigm has fully shifted to favor top talents in sports media in a manner that is truly unprecedented.
To get to where we are now, you have to think about the landscape in 2015. Some talents had big leverage — ESPN had to pay big to keep a lot of its roster from going to upstarts like NBCSN and FS1 — but it was nothing like it is today. Regardless of money, ESPN had the distinct advantage of the very real possibility that you could get lost if you left. Stephen A. Smith, now arguably the face of ESPN, had exited the company only to return after he never totally found his niche at Fox Sports Radio. Michelle Beadle left for NBCSN in 2013, the network canceled her show The Crossover after about seven months, and she too returned to ESPN the very next year.
Yes, Dan Patrick and Rich Eisen had and continue to have considerable success away from the Four Letters, but you have to remember that for a long time they were viewed as outliers. For most others who departed ESPN, even if they continued to have fine careers financially, there was less ‘glow’ on their work. In a business where the size of the audience that you reach has a lot of psychic implications on talents’ own sense of self-worth, this is not insignificant.
As I’ve written a couple of times, Dan Le Batard was amongst those who cautioned against Simmons, Cowherd, and Skip Bayless leaving ESPN. He talked about the magnificent audience reach they were yielding. He warned they would get lost. In what wound up being very fortunate as it pertains to his own circumstances, Le Batard has probably never been more wrong.
And it wasn’t just Simmons and Cowherd who succeeded at new destinations. Many who have left ESPN since 2015 — Jason Whitlock, Will Cain, Jemele Hill, Michael Smith, Emmanuel Acho, Tom Rinaldi, and we could go on for paragraphs — thrive financially and with visibility of their work.
Le Batard exited ESPN about a year before his deal was up, with his extremely valuable podcast feeds in his possession. The deal with DraftKings is just the start of what he and former ESPN president John Skipper will be tackling with Meadlowlark Media. It looks to be the start of a phenomenally lucrative business — and they’ll also have the autonomy to not just talk about whatever they want, but explore other content avenues across the media spectrum.
While ESPN no longer has a stranglehold on talent, they may not even wish to anymore. The company has fortified its ambitions more and more around live rights. They added UFC, they’ll have a monopoly on SEC football in a couple years, the NHL is coming back to them, and they got into the NFL’s Super Bowl rotation — without losing any of their cornerstone live rights as of yet. They of course need talent to fill their events and all their other hours, but they’re not nearly as concerned anymore about which people come, stay, or go.
The landscape had already shifted where top sports media talents found themselves with options not especially available to those in previous generations — before the sports gambling gold rush. To say that sports gambling has improved the fortunes for big names in media would be akin to declaring that a Stop sign is red. Gee, ya think?
But the scale is still so mammoth that we have to talk about it. Dave Portnoy, on his podcast last week, analogized that when Penn National bought Barstool at a valuation of $450 million it was like when the market gets set for a star quarterback and then the hurdle keeps getting subsequently cleared.
The gambling companies are fighting tooth and nail for user acquisition. According to Axios, DraftKings spent about half a billion dollars in marketing last year alone — and that was before they bought VSIN and inked a three-year, $50 million deal with the Dan Le Batard Show with Stugotz. FanDuel, MGM, Caesar’s/William Hill, Rivers, and Pointsbet are all also spending like crazy. Bally’s, Wynn, and Churchill Downs’ TwinSpires are coming as well. If I started naming all the partnerships that these gambling operators had in the sports media business it would be July before you finished reading this piece.
Whether and to what extent the general sports media audience wants the ongoing proliferation of sports gambling content, there’s only going to be more and more. If you think it’s already A Lot, wait until big states like New York, Florida, Texas, and California are legal and go live.
Jay Marriotti, writing for this web site, ripped Le Batard for getting in bed with DraftKings. “So let’s see if I have this straight: He painted his ESPN superiors as undesirable partners because they didn’t want him causing political wars on the radio … yet he’s ethically willing to jump headfirst into the gambling cesspool,” Marriotti wrote. “In the end, he’s the grimiest of all. In the latest example of desperation leading to hypocrisy, LeBatard’s lengthy search for a company to distribute his podcast led to DraftKings, the tout louts who will control ad sales and licensing arrangements. This will sink Le Batard’s show into the betting crapper and complete the demise of a once-great journalist.”
It’s easy to dismiss Marriotti as a scold, but there is a dark side to the relentless onslaught of gambling partnerships where media organizations that should theoretically be watchdogs to keep the industry honest are financially dependent on it. An unfortunate byproduct of the unrelenting marketing campaigns and easy access to gambling is that there will be addicts who lose everything. Relationships and families will be destroyed.
You can believe in individual liberty to support gambling legalization, and believe that it’s better to have it happening out in the open and regulated rather than in the hands of the mob, while also being sympathetic to the inevitable negative consequences. Before he signed the deal, Le Batard surely had to grapple with the idea that there are members of his audience who will get hooked and dig themselves a deep hole.
To be sure, hardly any of the marketing we see connected with our sports is healthy and pure. We are deluged with ads for prescription drugs where the side effects oftentimes sound worse than the symptoms they treat. Beer and liquor marketing remains massive. Is gambling worse for society than alcohol? It’s hard to argue that. And every time you watch sports, played by our planet’s healthiest citizens, there is a flood of commercials for the unhealthiest food.
Nonetheless, life is full of trade-offs. Le Batard, former ESPN president John Skipper, and Meadowlark Media faced the decision on whether to take the DraftKings deal and keep the show free for listeners, or to do his show behind a paywall — a move that Howard Stern pioneered when he went to SiriusXM in 2004. Certainly, Le Batard’s die hard listeners would have followed him to a subscription platform.
Ultimately, Le Batard and Skipper chose the route of maximizing reach and relevance, and they positioned themselves with the flexibility of evaluating the landscape in three years while maintaining control of their intellectual property.
No one can sit here and tell you that they actually know what is going to happen from the great gambling gold rush of the 2020s. It’s a good bet that the dozen or so players will consolidate into a half-dozen or less, but what permutations wind up happening are anyone’s guess. Eventually, the marketplace will be mature from a user acquisition perspective, but customer retention will remain paramount. Therefore, even if the sports media industry doesn’t maintain the insane boom times that are happening now, gambling partnerships will stay a component of the business for perpetuity — the business has been mature in Europe for awhile, but you still see ads for sportsbooks plastered all around soccer fields and even on players’ uniforms.
The bottom line is that the top talents in this business have an unprecedented amount of leverage. The ones in the best position now, besides Portnoy where Barstool is a remarkable story of entrepreneurial organic growth, capitalized on the power of big media organizations to build their own portable personal followings. These followings are enormously valuable across linear and digital platforms, and this is exponentially true if those followers are loyal enough to follow the talents to a specific gambling app. In 2015, it was a real risk for Bill Simmons and Colin Cowherd to spread their wings outside of ESPN (yes, Simmons was fired by Skipper and thus had no choice, but he has repeatedly said it was his plan to leave when his contract expired). In retrospect it can seem like their choices were obvious, but the present boom times for popular sports media personalities can be traced to that stretch.
Ryan Glasspiegel is a contributor for BSM. He has previously worked for Outkick, The Big Lead, and Sports Illustrated. In addition to covering the sports media business, Ryan creates promotional products for brands and companies including t-shirts, hats, hoodies, and various types of swag. For business inquiries email him at Glasspiegel.Ryan@gmail.com or find him on Twitter @sportsrapport.
