This Is Jack Easterby’s World

“Love it, love it, love it,” Erika Nardini said. This was in 2014, and she had just been handed a drawing of "a bear wearing zebra-print pants and a shirt covered in ones and zeros" by an elfin 44-year-old Australian man known professionally as Shingy. At the time, Nardini was the chief marketing officer of AOL Advertising; Shingy, who left AOL in the fall of 2019, held the professional title of Digital Prophet. What that meant, Shingy told The New Yorker's Andrew Marantz, was that he flew around the world going to conferences, thinking and talking about the future of Storytelling, and other esoteric elements of being online that might emerge in intriguing and profitable ways in the future. “I’m thinking of the bears more as a metaphor,” Nardini ventured. One thousand percent, Shingy replied.

"Shingy is my muse," Nardini told Marantz, who noted that Shingy was blithely booping around on his phone as she spoke. "I lean on him really heavily for the feel of what’s happening in the here and now. There is something so polarizing about Shingy, but also so unifying." If this does not clarify what a Digital Prophet is, or does, or might possibly be for, it also clears things up in ways that an actual job description could not. Muses don't need to show results, or produce anything beyond the sort of vague and recursive smuggeries—so polarizing, so uniting—that qualify as higher-order thinking among apex business types. If Shingy had some prophecies on how and where people would be messing around on their phones in the future, all to the good. But the industry in which he and Nardini and their peers worked was about persuading brands to communicate their message to humans in certain ways. This meant that they were mostly in the business of making certain types of sounds.

What was for sale was a feeling, and an understanding of what the people with the money wanted to feel was at the crux of everything. You, the person reading this, may not find yourself terribly compelled or convinced by Shingy's message that this adventure in online storytelling—which was, and is, literally digital marketing—was all terribly interesting and fun, let alone more like art or prophecy than anything else. But that message is not for you. The game, which is much older than Shingy, is about the fine points of flattery, and identifying what kind of game the various softheaded lordlings who have the money want to believe they're playing, and then making sure they have a good time playing it.

Sometimes the world seems to be closed off in ways that once was not. Really, though, it's more the case that our current killing stasis is just much more closely administered than it used to be. Gone, for the most part, are the good old days when, say, a plucky monk with a shadowy history could wind up beguiling Russia's ruling family on the strength of his piercing gaze and pure predatory charisma. It is not that our ruling classes have gotten any less fatuous or readily beguilable, lord knows. The more ambitious among them have created an ad hoc ideology out of their stupid broken ideas and a very real boutique economy centered upon legitimizing their pissy preferences as a worldview and enshrining them as actual policy; the average contemporary lord, though, just wants to be taken care of, and told they're brilliant and blameless and correct.

There is still a good if parlous and paranoid living to be made in the sycophant business, but the barriers to entry are high. It took Jack Easterby years, for instance, just to get himself into a position from which he could skeeve his way from a quasi-pastoral role into control of a NFL franchise without any evident merit. Once he got close enough to the owner to be heard, though, it happened much faster.

"One lower-level athletic department staffer during Easterby’s time at South Carolina put it this way," Sports Illustrated's Jenny Vrentas and Greg Bishop reported in their definitive story on Easterby's irresistible rise to become the prime mover for the Houston Texans. "'When it was just us, he’d want to know how you were doing and wanted to help you in any way he could.' But if an important coach or player walked into the room, 'it was like, all of the sudden, you didn’t exist.'" It was during his time at South Carolina that Easterby met Texans owner and USC alum Bob McNair, who showed up to give a 10-minute talk about character. Vrentas and Bishop write that Easterby sat in the front row.

Easterby was the Gamecocks' character coach then, a sort of utility chaplain whose job seems to have been the provision of churchified inspiration and support for any and all who needed it—to be "the seeds and water of truth, love, and support to grow people and have them be encouragement-oriented," as Easterby described it to the New England Patriots' team site in 2018. There was naturally a Shingy-ish dimension to his job, too, which involved delighting his superiors with the sort of Successories-grade pabulum that certain coaches treasure above all things.

Easterby did this job at South Carolina, and then for the Kansas City Chiefs, and then with Bill Belichick and the New England Patriots until 2018. His shtick played better in some places and with some people than others, but when it worked, it worked. That story on the Patriots team site features player after player praising Easterby for his availability and support and good fellowship. In Houston, it was different. His folksy sermonizing put players off; the locker room and his fellow execs all distrusted him. "Multiple Texans from Easterby’s tenure say they began to watch what they would say in conversations with him," Vrentas and Bishop write, "nervous that the culture coach was looking for reasons to move out people with different values or lifestyles." Players believed they were being followed, or otherwise monitored. This is not the first time that an organization that pursued a Patriot Way personality transplant reported this sort of suspicion, or activity, but it is hard to think of an instance in which those suspicions were more quickly or decisively proven correct than with Easterby in Houston.

In April of 2019, Easterby joined the Texans "because he knew the late Bob McNair from South Carolina, and believed the McNair family's values aligned with his," ESPN wrote. In June of that year, the Texans unexpectedly fired GM Brian Gaine after 17 months on the job; the team sought an interview with Nick Caserio, the Patriots executive they'd later hire as GM in January. That request that was denied by the Patriots, who subsequently filed a tampering charge. "Although there was speculation Easterby talked to Caserio about the job at a Patriots ring ceremony that took place the day before Gaine was fired," ESPN wrote, "Belichick told reporters the week before the teams played in 2019 that the tampering situation 'didn't have anything to do with Jack Easterby.'" Head coach Bill O'Brien took over Gaine's job, although Vrentas and Bishop reported that many in Houston's locker room blamed Easterby for the disastrous trade of DeAndre Hopkins.

When O'Brien was fired, Easterby stood alone atop the organization until he finally managed to bring Caserio in, at which point the organization began a sprawling purge of team employees who represented rival power centers in the organization, from long-tenured executive Jamey Rootes (who was pushed out) to franchise quarterback Deshaun Watson (who wants out). It is difficult to imagine what the Texans will look like next year, beyond that they will look more or less the way Easterby wants them to look, and the secondary certainty that they will not be much better than they were last season.

The rubbernecking appeal of all this is interesting enough, and a pious schemer like Easterby makes for a suitably unctuous villain. "If you combine a faith-healing televangelist with Littlefinger," one of Easterby's colleagues told SI, "you’d get Jack Easterby." But also, just given the fact that we are talking about a NFL team and the blundering billionaire scion in charge of it, there is not very much to any of it. This sort of oafish dumb-guy intrigue and ham-brained executive power politics is standard NFL stuff; it's what ambitious dunces generally do instead of their jobs. Even as decently representative microcosms go—and this is decently representative at least in the sense that everything in the last presidential administration was also like this—it is also a noticeable tick dumber than it needs to be.

There certainly is nothing much new, here. Easterby's brand of self-interested service and glib churchery is a product that is very popular in America; there is an audience for it, always and everywhere, but Easterby needed a patron, not a flock. He found the audience that mattered, and secured it. In response to a reader who asked why he has risen and risen despite the fact that he "appears to be the named source of discontent by players, front office personnel, fans, sports writers and radio talk show hosts," the Houston Chronicle's John McClain wrote. "The McNair family likes Easterby and believes in him. Obviously, they’re convinced he knows what he’s doing."

None of that quite accounts for why I've found myself so perversely fascinated by the silly and sordid saga of this mediocre cynic's rise to a position of power. The little details are satisfying enough, but Easterby's fudged résumé and backchannel scheming and all the rest is familiar, too. It's the stupid shape ambition takes when performed by people who don't want anything but power. Of course it is artless. Every power struggle is stupid, and fundamentally more or less the same—it is men pushing each other out of the way and guarding against being pushed out of the way in turn, because they want to be in front. None of it signifies anything. It's like the games that dogs play.

But Easterby's gambit also fits perfectly into this blank and wildly overt bigger moment. Even as the tide rushes out, there is plenty of power and plenty of money around; the wrong people have both, and want nothing more than to keep them, and there is no force for accountability, and people suffer for it. In the face of hardship and suffering and vast need but also on its own criminal merits and in its rude and childish selfishness, this is infuriating. All of it is exactly what it appears to be; no one involved feels compelled to conceal any of it, because they cannot conceive of being held accountable. At scale, this abdication creates the condition for sprawling and horrific crimes. The shame of it is so vast as to make it incomprehensible.

But this is smaller, and so easier to see. In the Texans' front office, it all looks exactly as shameful and shabby as it is. A cheesy striver whispers self-serving pieties into the ear of an easily distracted rich man, over and over, because it is his job. The rest goes about as you'd expect.