Sports Illustrated – His path to the top of the Houston Texans’ front office is unlike anything the NFL has ever seen. Many from his past see him as a chaplain with a heart of gold or an underdog outsider with the tools for greatness. Others are skeptical, unable to square his relentless ambition with claims of selflessness. Two years after his arrival in Houston, those inside the Texans’ building describe an atmosphere of mistrust, a state of constant chaos and a sense that he isn’t fit for the roles he’s taken on…Then there was Jack Easterby, hired as the franchise’s executive vice president of team development in April 2019, a man who’d risen from low-level Jaguars intern to Patriots team chaplain to lauded character coach—before making an unprecedented shift into football operations. Easterby, those Texans told each other, was Littlefinger, the nickname of Petyr Baelish, a shadowy and cunning operative who on TV espoused righteousness as a strategy, but sought to consolidate power through chaos and isolation and the pulling of strings behind the scenes.
Chaos is a ladder. This is a blog I meant to write back in October, but never got around to it because I’m a perpetual procrastinator. The headline of that blog I never wrote was: “With Bill O’Brien Fired, Jack Easterby is Officially the Petyr Baelish of the NFL.” A guy who was hired to be a chaplain, a glorified character coach for the Patriots, somehow rose to the rank of General Manager for the Houston Texans. How the fuck did that happen? Seriously, Easterby should walk around with a mockingbird sigil pinned to his chest.
I often thought my disdain for this man I never met was just my Patriots red and blue bleeding through after Easterby trashed Robert Kraft on his way out of New England because he *allegedly* got an HJ from another adult. People that act holier than thou are usually the worst ones behind closed doors. Well, turns out it wasn’t just me as Sports Illustrated just published an extensive article TRASHING Jack Easterby and also borrowing my Baelish analogy.
Long story short, Easterby worked his way up from camp counselor to college character coach to chaplain for teams like the Chiefs and Patriots, before heading to Houston for a promotion in Player Development (Easterby then also tried to poach Nick Caserio while at Kraft’s house for a Super Bowl ring ceremony), and then *nine* months after being on the job for the Texans, he somehow slides into the EVP of Football Operations/GM role after the vacuum left by the firing of current GM and coach, Bill O’Brien.
THAT is some ladder climbing folks.
Easterby’s role wasn’t clearly described to many of his new colleagues, but he was expected to build on the position he held in New England, setting an organizational culture and mentoring players.
These are the kinds of hires that are always disasters in companies because if nobody really knows what somebody is supposed to be doing then it allows them to, at best, be unproductive and at worst work in the shadows to craft their own job description.
One former staffer says that when Easterby is asked for specifics about a subject on which he’s out of his depth—not uncommon considering his scope of responsibilities and limited NFL experience—he’ll artfully deflect and move on to a new topic. They watched curiously as Easterby’s responsibilities expanded well beyond the role for which he was hired—in some cases, outside his areas of expertise. As another colleague puts it, “Jack was basically doing everything O’Brien was doing, except for calling plays.”
See what I mean?
But you seriously have to read this entire SI article just to see the long winding road a guy with zero actual NFL chops somehow jumped from position to position, manipulating relationships (and to be honest probably naive, hyper-religious people) from team to team, until he somehow went from character coach to the guy in charge of a National Football League franchise. Unreal, you almost have to respect it.
While Easterby aspires to be a transformational leader, guided by religion and morality, people who have worked alongside him in Houston have increasingly come to see him as transactional. Says a colleague: “If you combine a faith-healing televangelist with Littlefinger, you’d get Jack Easterby.”
The one thing that I can’t seem to figure out is his apparent close relationship with Belichick. You would think this is a guy Bill would tell to get the hell away from him. He has always been distrustful of charlatans like Tom Brady’s guy, Alex Guererro. Although it seemed like his act may have been wearing thin and more people were starting to wise up in the Patriots organization.
One person who saw his sideline histrionics up close says they were more show than substance: When you see him and the big personality and how he’s moved up the ladder so fast, you’re like, ‘Man, this isn’t authentic. Something doesn’t feel genuine about this.’ ” Others saw him sidling up to assistants. They noticed that he hired an agent who represented coaches and executives, an unheard-of move for a chaplain in pro sports. One Patriots staffer compared Easterby to a preacher at a megachurch—a man of God who stands onstage and denounces the ills of poverty, then slips out the backdoor, into a private jet. Several current and former colleagues, from Foxboro and Houston, agree that this description is accurate.
Theres also a ton of stuff in there about Easterby seemingly straight up lying on his resume and experience such as helping 50+ universities in their coaching searches over the years without offering any specifics. Until he got called on it that is.
As recently as November, a bio for Easterby that appeared on the website for the Greatest Champion Foundation (a nonprofit with a goal of serving athletes holistically through faith and founded by Easterby and his father) claimed that Easterby has over the years “been entrusted with over 50 head coaching searches at both power-five and mid-major universities for multiple sports.” Neither the Texans nor Easterby addressed specific questions from SI about which programs he has worked with on coaching searches and in what capacity.
That foundation’s site was down for most of the past month—a staffer explained that it was due to a redesign and migration to a new content management system—and when the new version launched last weekend, Easterby no longer had a bio.
It seems like the Texans may finally be wising up to Littlefinger’s act of ladder climbing as well. Apparently they sent out an email to all season ticket holders announcing a star studded team devoted to finding the next GM and coach of the team. Just as it ended for Baelish, you can only climb so high on trafficking misinformation before you make enough enemies that it catches up to you.
After reading that absolute hit piece by SI though, if I had to summarize Easterby in one gif, it’s this.
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