‘Character’ Flaw: Jack Easterby’s Time With Patriots Foreshadowed Acrimonious End With Texans

Despite some positive contributions, Jack Easterby’s tenure in Houston will forever be shrouded in controversy, as was his time with the New England Patriots.

At long last, the Houston Texans have parted ways with now former executive vice president of football operations Jack Easterby.

Easterby, who was originally hired in 2019, had been the subject of much controversy, and by default, much scorn from Texans fans, and media alike, during his tumultuous tenure in Houston. 

From questions surrounding his qualifications to overt mishandlings regarding the situation of ex-Texans quarterback DeShaun Watson, Easterby’s exit from the organization has seemingly been long overdue.

Of course, Houston may have had second thoughts about hiring Easterby, simply by taking a deeper look at his tenure with the New England Patriots for a reference.

From 2013-2019, Easterby was considered one of the most-liked people in the Patriots organization The team originally brought him in as a team chaplain following the Aaron Hernandez murder scandal as a presence in the locker room to help players off the field. 

He described his work as "to serve the players mentally, physically and help them as people.” He also helped the team with drills, draft evaluations, helped orient new players, and held Bible studies and religious services. Easterby would later be known as the Patriots ‘character coach.’

Initially, his contributions were well-received by Patriots coach Bill Belichick, as well as team standouts such as special teams captain Matthew Slater and wide receiver Julian Edelman. As his popularity grew, so did his role with the team.

Here, as they say, is where the plot thickens.

Easterby’s increase in organizational stature apparently gave him a bit of a wandering eye, so to speak. He and his agent Bob LaMonte reportedly began to explore his opportunities to make a jump to a bigger opportunity within another organization. Still, he needed an additional reason to help facilitate his eventual exit from the Patriots, where he had built a strong and loyal reputation. 

As such, Easterby left the team early in 2019, shortly after it was announced Patriots owner Robert Kraft would face two first-degree misdemeanor solicitation charges in Palm Beach County, Florida. Citing a conflict with his personal ethics, he was now free to move about the country.

The back-channel search came to an end, when Easterby signed with the Texans, after Houston outbid teams such as the Miami Dolphins, along with several NBA organizations. Back in Foxboro, however, the news was reportedly not met with warm well-wishes. 

In fact, a number of media outlets at the time reported that several key members of New England’s brain trust felt betrayed by the ‘cloak and dagger’ manner in which Easterby handled his aspirational job search. 

They were especially angered by his taking intricate knowledge of team operations to the Texans, who were coached at the time by ex-Pats assistant Bill O’Brien. Lastly, they felt that Easterby used Kraft’s legal difficulties simply as a media pawn to make his leaving New England seem more palatable.

The animosity apparently came to a head on June 6, 2019, when the 2018 Patriots received their Super Bowl rings in a ceremony held at Kraft’s private home. 

The event commemorated the Pats' record-tying sixth Super Bowl Championship, via a 13-3 victory over the Los Angeles Rams in Super Bowl LIII. While the pomp, circumstance, and ‘bling’ were the most prominent highlights, the evening has now taken on a different type of significance.

In fact, it not only caught the attention of the Patriots organization, it was brought to the attention of the NFL, as well.

Both Easterby and former Pats director of player personnel, Nick Caserio were members of the 2018 Patriots staff. As such, each was present at the party. However, the usually benign socializing between two former friends and colleagues sparked a cause for concern among New England’s brain trust, particularly with Caserio still under contract to the Patriots.

Just one day removed from the ceremony, the Texans fired general manager Brian Gaine, following an 11-5 finish to the 2018 season. The Texans had won the AFC South division and earned a spot in the 2018 NFL Playoffs, leading some to question the timing and motivation behind such a move.

While Gaine’s questionable personnel practices were initially blamed for his dismissal, some have pointed to Easterby’s connection to Caserio as an underlying, and potentially more prominent reason. 

In the aftermath of Gaine’s firing, the spotlight shined squarely on the promising Pats executive, as a possible replacement. The Texans (with O’Brien as both coach and general manager), had tried to interview Caserio for positions within the organization in previous years. However, the Patriots denied their requests.

With Easterby and Caserio being represented by the same agent, Bob LaMonte, the Pats took umbrage at their interaction to the point where tampering charges were filed against the Texans. 

In turn, Houston publicly disavowed their interest in Caserio, who remained in New England through the 2020 season. He would officially join the Texans in 2021 as their general manager.

Despite Caserio’s eventual departure, Easterby remained at the center of the firestorm from a Patriots perspective. That same questionable specter followed him to Houston, where his positive contributions to the organization were far outweighed by the controversy he now leaves behind.

At 1-3-1 through five games in 2022, the Texans are hoping that their struggles fail to outweigh the promise of an offseason in which they are flush with salary cap shape and have extra first- and third-round picks in 2023 and extra first- and fourth-round picks in 2024. Whether Easterby’s exit signifies a front-office rebuild or is just an isolated incident, remains to be seen.

This time, however, the Texans will take on the future with a greater sense of ‘caveat emptor.’ 

After all, Easterby’s history in New England foreshadowed his turbulent time in Houston. 

It should serve as a cautionary tale to not get fooled again. 

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