Stephen A. Smith got a five-year, $100M deal from ESPN, and he just might be underpaid

A little more than 23 years ago, there was a column written (by I) about the “Meaning of Michael Vick’s $100M contract.” At the time, Vick had returned to the NFL, was playing for the Eagles, had spent time in jail for his role in a dog-fighting ring, had been considered public enemy No. 1 in the eyes of America and, as a black (insert N-word) quarterback, was not only a threat to the NFL QB status quo but also in many, many societal circles was undeserving of a payday that reflected everything $100 million represented.

History doesn’t necessarily repeat itself as much as it is remixed.

Last week, that remix came in the form of ESPN’s Stephen A. Smith, after 10 months (275 days to be exact, according to him) of actual negotiations, signing a deal to stay with the Disney-owned conglomerate for the next five years to the tune of, yup, $100 million.

A number, annually and in totality, making him the highest-paid talent at the largest sports network in the world and the highest-paid non-former athlete in modern-day sports-media history, while also shifting the landscape in today’s new sports media of what the future can (not necessarily will) look like for non-ex-pro athletes in broadcast journalism.

It’s his form of sports journalism-shared-performance art that society can’t move away from. And doing so in a way — his way — that no one else in the business of global sports media can replicate, recreate or capture. And it’s in the non-former-athlete space that makes Smith’s latest contract not just different but what gives it a different meaning.

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Pioneers might not get paid, but damn it, now in this game, pundits got a chance. He got Myles Garrett money without doing Myles Garrett things. Put a whole ’nother way: The bag got heavy.

Generational money that people who cover sports yet never played them at their highest level rarely in two or three lifetimes ever see. What makes Smith’s deal so seminal is generational money, especially when attached to a black male in an industry in which those who look like him and myself have been historically underrepresented. It needs to mean something different to us besides hearing it attached to sports, entertainment and wrongful-incarceration settlements.

SAS’ bag just started a new conversation of us in this media lane. He is, like he loves to call others in this sports (media) arena, “box office.”

Single-entity black capitalism at its highest in front-facing media. Is he worth the $100 million? Yes, 100%. When you are, have become and have elevated yourself to being the “face of” anything that has a $24 billion valuation (as is ESPN’s, according to a Bank of America Global Research analyst note from 2023 and reported in Forbes the same year, even as that number is an estimated 50% drop from 10 years before), $100 million ain’t s—. Easy money over a five-year period to the human “brand” who has become as synonymous to a network (read again: a whole network!) as Kleenex is to tissue, i is to phone, Netflix is to chill.

That written, always keep in nuanced perspective: Tom Brady is far from the “face of” Fox/Fox Sports, yet the quiet “not worth the contract” whispers seem less loud for someone (even if it is Brady) who signed a deal close to four times in total — $375 million over 10 years — what SAS’ deal was for with far less on-air presence, but let’s digress.

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The $100 million has other outlets referring to Stephen A. now as the ‘‘sports-broadcasting GOAT,” a “media mogul,” the industry’s “most powerful pundit,” “the world’s most famous media member,” “the king of TV” (as they sang upon his “Coming to America” entrance on the Gil’s Arena podcast), “Dr. Stephen Nai-Smith,” as he likes to refer to himself.

It’s called the “Stephen A. Smith business” for a reason.

Make zero mistakes, it’s the love/hate relationship the world (even outside of sports) has with him that has been more beneficial to how he, Mark Shapiro and Endeavor parlayed his deal with ESPN than anything else placed on the table. Even his legendary work ethic, which makes it hard for many people to place the hate part over the love part when expressing their true feelings about him, might not be enough to justify in many minds an offer of that nature even being negotiated with his name on it.

It means that polarization matters. Well, not just polarization but the popularity of polarization. How love/hate within that construct means so much more. How it has become both cash cow and power play in America. Say what you want about SAS, but rarely has anyone in American (sports or anything) media ever played the value and negotiating game like Stephen A. just did.

Dramatic, yes. Over-the-top and loud, always. Being bigger than what he represents, not anymore. Now that he has been “franchise-tagged.” In the best meaning of the term.

During the whole process, Smith kept saying, to self and to those of us in position to speak with him, it was all about “measuring his worth.” He has done it. Now you, the reader, do it. Measure his worth. In the industry, to ESPN, in society at large, in what it means. See what you come up with. Love him or hate him, you’ll conclude, unlike Vick over a generation ago, the new n—– the world loves to hate still might be underpaid.

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