Last September, Skip Bayless’ contract with Fox Sports was up, which was interesting timing considering the furor Bayless created that month with his “I don’t have sympathy for him going public” take on Dak Prescott’s comments about battling depression following the death of his brother, followed up with an unsigned Fox statement and a Bayless non-apology. If Fox had wanted to move on from Bayless and his often-toxic takes (to say nothing of his hefty price tag of $6 million annually) , that timing would have been an opportunity like no other to become the “more mature network” Fox Sports president of national networks Mark Silverman claimed they were in May 2019. But Fox predictably kept trying to extend Bayless anyway, and while that extension was never officially announced (perhaps thanks to the furor around the Prescott comments), Bayless remaining on the air suggested that a deal had been struck.

Now, almost half a year later, Andrew Marchand of The New York Post has the details on Bayless’ new deal with Fox. As per Marchand, that deal is for four years and $32 million ($8 million annually, a $2 million raise), may come with a second afternoon show, and came after an ESPN attempt to bring Bayless back and again pair him with Stephen A. Smith (but for an ESPN+ digital show rather than a new version of First Take). Some highlights from that piece:

ESPN made a full-court press to reunite Skip Bayless with Stephen A. Smith, The Post has learned.

The duo would have done a daily ESPN+ show together, while being splashed over ESPN, including weekly spots on the “Monday Night Football” halftime show.

After lengthy negotiations, it culminated in Fox Sports retaining Bayless with a four-year, $32 million contract, according to sources.

As part of the agreement, Bayless, a professional provocateur, continues to do his daily morning sports debate show on FS1’s “Undisputed” with Shannon Sharpe and host Jenny Taft. Bayless and FS1 are in the early planning stage of a potential second daily show for the afternoons. At this point, Bayless is expected to be a solo act for the program.

It’s certainly notable that ESPN reportedly went so hard at Bayless (with a four-year offer somewhere between $26 million and $31 million, as per Marchand), and that they seemingly weren’t going to just put him back on First Take, but rather have him do other appearances with Smith. And the ESPN+ show idea there is particularly interesting; while ESPN+ is doing well in terms of subscribers (12.1 million as per a Disney earnings call last month), many of those are from the bundle offering with Hulu and Disney+, which makes ESPN+ essentially a free throw-in.

Beyond that, it looks like a significant number of people subscribe to ESPN+ for particular live sports rights, but then cancel after those sports’ seasons. High-profile studio programming might be an attempt to keep some of those subscribers around year-round, and while the merits of Smith and Bayless can definitely be debated (heh), they undisputedly (heh) have their fans. Smith already has a Stephen A.’s World show on ESPN+, but a Smith and Bayless program would certainly have drawn more attention.

Another tidbit of note in Marchand’s piece is that ESPN continued trying to land Bayless for a digital show with Smith even after he agreed to stay with Fox. That plan would have had Bayless and Smith continue with their morning debate shows on FS1 and ESPN respectively (with Shannon Sharpe and Max Kellerman respectively), but then team up for an afternoon show on ESPN+. And it’s interesting that this didn’t happen, as in a lot of ways, that would have seemed to make sense for both sides; both Fox and ESPN could have gotten whatever “benefits” there are from having Bayless on their platforms without having to pay his full salary. But Marchand’s piece says there were “too many hurdles” for that idea to come to fruition.

In the end, it does feel somewhat surprising that Fox not only kept Bayless, but gave him a 33 percent raise over his last deal and signed him for four more years. He’ll be 72 in December 2023, which makes him significantly older than most daily studio show personalities. His show also doesn’t seem like as much of a fit for Fox following Jamie Horowitz’s 2017 firing; Horowitz took over First Take in 2011 and turned it into the Skip and Stephen A. “Embrace Debate” fest we all know, so it was logical that FS1 brought in Bayless during Horowitz’s attempt to pivot the network to takes. But Silverman has seemed much more lukewarm on that strategy, even claiming “We’ve grown past embrace debate” in 2019. Apparently they haven’t entirely grown past it, as the continued spotlight for the likes of Bayless and Colin Cowherd shows.

It’s also interesting to see Fox paying Bayless so much here. $8 million a year is a significant amount, and that’s especially true for a network that really isn’t trying to challenge ESPN head-to-head any more, unlike in 2013 when they launched or 2016 when they brought Bayless in.  Two factors that probably contributed to that are the big-ticket contracts ESPN has been handing out (“nearly $8 million” annually for Smith in 2019, $6.5 million a year for Mike Greenberg in 2016; keep those deals in mind whenever they announce giant company-wide layoffs) and the amount ESPN was reportedly willing to offer Bayless.

There is some logic for Fox in keeping Bayless. While Undisputed does not draw particularly well in the grand scheme of things (it averaged 107,000 viewers Wednesday, 109,000 Tuesday and 145,000 MondayFirst Take, by comparison, drew 287,000, 324,000, and 372,000), it does seem generally okay for a channel with FS1’s current low profile. (It was their most-watched show Monday, and behind only The Herd Tuesday and Wednesday.) And it does tend to do better during NFL season and during the NBA playoffs. But it’s certainly not clear that those numbers are worth the amount Fox is shelling out.

From the outside, it might seem like Fox could get better value for their money by replacing Bayless with someone cheaper (and perhaps also more insightful). But they’ve elected to stay the course here, determining that the attention Bayless brings is worth his hefty price tag. And perhaps they can get some more value out of him still if this proposed afternoon show comes to fruition. This deal also means that Bayless remains one of the few especially prominent sports personalities not under the ESPN umbrella, and there’s probably some value for Fox there too. Whether that adds up to $8 million a year in value can be debated, but Fox management clearly thinks so.

[The New York Post]

About Andrew Bucholtz

Andrew Bucholtz has been covering sports media for Awful Announcing since 2012. He is also a staff writer for The Comeback. His previous work includes time at Yahoo! Sports Canada and Black Press.