Jul 11, 2021; Milwaukee, Wisconsin, USA; ESPN reporter Stephen A. Smith prior to the Phoenix Suns against the Milwaukee Bucks in game three of the 2021 NBA Finals at Fiserv Forum. Mandatory Credit: Mark J. Rebilas-USA TODAY Sports Credit: Mark J. Rebilas-USA TODAY Sports

Stephen A. Smith, at one point in his career, could have been considered a journalist. If you asked Stephen A. to label himself now, he’d probably prefer “entertainer.” And while that would certainly be an accurate description of the larger-than-life 56-year-old, a shrewd performer whose cartoonish stylings have come to define debate television, Smith, more than anything, is a kingmaker, a ruthless despot wielding his power and influence over the sports media-sphere like Caesar in a Tom Ford tunic.

Positioned as the face of ESPN, if not the entire industry, Smith’s loyalty to the worldwide leader will be tested in the coming months as the sides work toward a new contract, the threat of Stephen A.’s departure looming over Bristol like a storm cloud ready to burst. Stephen A., throughout his ESPN tenure, has prided himself in being a company man, a humble servant (albeit one with an eight-figure salary) devoted fully to his craft, working impossible hours in service to a network that, as recent layoffs would attest, has often treated talent as expendable.

At first, Smith took the high road when ESPN rewarded newcomers Pat McAfee and Troy Aikman with exorbitant salaries ($17 and $18 million a year, respectively). However, Smith wasn’t nearly as diplomatic in his recent appearance on OutKick the Show with Clay Travis, taking the snub personally while vowing to become the highest-paid personality on ESPN.

“I have my own production company. I’ve got my own YouTube channel. I’ve got my own show,” said Smith, referring to The Stephen A. Smith Show, his recently-launched podcast that often delves into subject matter outside of sports including politics and pop culture. “The list goes on and on. I’m doing all these things. I’m not doing all that to be in second place.”

Smith has always been outspoken, but he’s been increasingly demonstrative of late, picking at old scabs by beefing with Dan Le Batard (who criticized Smith and longtime rival Skip Bayless for making sports “dumber” by treating every issue as binary, muddying the discourse with mindless clickbait at the cost of nuance) and repeatedly antagonizing his former First Take sparring partner Max Kellerman.

Stephen A. seems to be on the warpath, throwing caution to the wind with risky segments touching on everything from Ron DeSantis to concerning allegations made against Dwight Howard. Emboldened by his new platform on Audacy, Smith has never been edgier, spreading his wings as the most reckless, unfiltered version of himself, a magnet for controversy churning out viral soundbites at a prolific clip. Is Stephen A. blowing off steam, acting out amid contentious contract negotiations, or is this a conscious pivot, re-branding himself as an unrepentant shock jock tired of beating around the bush? As usual, with Smith, it’s hard to tell.

From his loud suits to his frequent outbursts on First Take, erupting on nemesis “Mad Dog” Russo (the Washington Generals to Smith’s Harlem Globetrotters) with the fury of 1,000 suns, Smith has never shied away from attention, inviting the circus wherever he goes. Like your favorite wrestling heel, Smith is a showman at heart, suggesting the very real possibility that his contract strife is an invented plot line played up for dramatic effect, a clever trope that Stephen A., until his inevitable payday, can mine for content. Soon enough, we’ll know whether Smith is bluffing, peacocking like the sports divas he spends so much of his day talking about, or if this is where he and ESPN go their separate ways, dissolving one of the most successful partnerships in the history of sports media.

Posturing or not, Stephen A. has leverage. His empire has expanded rapidly, achieving a level of celebrity almost unprecedented in sports media. Smith’s ambitions outside of sports include acting (he’s appeared as a recurring character on General Hospital for the better part of a decade), the written word (his best-selling memoir Straight Shooter hit shelves earlier this year) and, someday, making waves on the talk-show circuit (he filled in as a guest host for Jimmy Kimmel during his summer hiatus in 2021), coming for the throne currently occupied by late-night impresarios Jimmy Fallon and Stephen Colbert. That would be a pipe dream for anyone but Smith, an adrenaline junkie who never backs down from a challenge, overcoming countless career obstacles in ascending to made-man status.

Thanks to wily transaction hounds like Adrian Wojnarowski, insider culture has quickly permeated sports, with fans sweating the trade deadline and free agency almost as much as the games themselves. That’s also true of sports media, where turnover is at an all-time high, fueled by streaming, an explosion of broadcast rights money and the collapse of RSNs (regional sports networks), among other contributing factors. Sports media in 2023 may as well be the Wild West, a revolving door of talent that, if ESPN isn’t careful, may just cost them its golden goose.

For all his flaws as an analyst, losing Smith would be an enormous blow to ESPN’s credibility, putting a company that was already struggling on the fast track to irrelevance. Replacing a pundit of Stephen A.’s caliber would be difficult bordering on impossible, though if it came to that, doubling down on McAfee would make sense. While not as seasoned, McAfee can at least match Smith’s energy and would fit ESPN’s narrative, going all in on football, which already accounts for most of their programming. With legacy media on its last breath, the time for experimentation is over with ESPN needing something solid to rest its head on. And what’s a more reliable revenue stream than America’s national obsession?

Despite the enticing prospect of reuniting with Bayless on Undisputed, Mike McCarthy of Front Office Sports doesn’t see Fox as an option for Smith, specifically citing their lack of NBA broadcast rights. Smith has made no secret that basketball is his bread and butter, though ESPN is at risk of losing its NBA rights when they expire after the 2024-25 season, with NBC, Amazon and Turner among their likeliest competitors in that space. If that were to happen, would Smith consider lending his talents to an up-and-comer like DraftKings (home to Le Batard, Mike Golic and others) or even go independent, taking the Bill Simmons approach in pursuing his own artistic vision? That would be a tricky hill to climb, though, after years of answering to Disney, Smith would surely prefer to be his own boss, favoring a collaborative environment free of corporate interference.

The irony of Stephen A. is that, for all the talking he does on television, it’s hard to know what he actually wants. With Jimmy Pitaro teasing a direct-to-consumer model that could take hold as early as 2025, does Smith see the writing on the wall, plotting his escape before ESPN goes belly up? Or is Stephen A. merely ready for a new kingdom to conquer, lamenting the monotonous, rinse-and-repeat nature of the sports news cycle?

Smith craves airtime too much to make himself a distraction the way disgruntled athletes often do when contract talks are at an impasse (one of James Harden’s favorite tactics). It’s fun to speculate, dreaming of an alternate reality where Stephen A. leaves the safety net of ESPN, representing a seismic power shift in sports media. But let’s not kid ourselves—this is, and always was, about money. Smith knows his worth and is willing to draw a line in the sand to get it, putting everyone in Bristol’s orbit on notice.

“You’re not doing it for the money. You’re doing it for what the money says,” Jonah Hill’s character, Peter Brand, tells Billy Beane (played by Brad Pitt) in the closing scene of Bennett Miller’s Academy Award-nominated Moneyball. “And it says what it says to any player that makes big money—that they’re worth it.”

Is Smith being petty? Maybe. But he’s also ESPN’s heart and soul, and that costs a little extra.

[Front Office Sports]

About Jesse Pantuosco

Jesse Pantuosco joined Awful Announcing as a contributing writer in May 2023. He’s also written for Audacy and NBC Sports. A graduate of Syracuse’s S.I. Newhouse School of Public Communications with a master’s degree in creative writing from Fairfield University, Pantuosco has won three Fantasy Sports Writers Association Awards. He lives in West Hartford, Connecticut and never misses a Red Sox, Celtics or Patriots game.