DeSean Jackson speaking (left). Stefon Diggs looking on (right).DeSean Jackson (left) and Stefon Diggs (right) (Photo by Sarah Stier/Getty Images).

Former NFL star wide receiver DeSean Jackson proposed an interesting theory regarding Stefon Diggs’ desire to leave the Buffalo Bills.

On Wednesday, the Bills traded Stefon Diggs and two late-round picks to the Houston Texans in exchange for a 2025 second-round pick. The Texans adjusted Diggs’ contract which now makes him eligible to enter free agency next year.

Speaking to Kay Adams’ on “Up & Adams”, Jackson suggested that Diggs sought a trade from Buffalo because the latter didn’t think that his Bills could defeat the Kansas City Chiefs.

“It was more of him wanting to win, I think. I don’t feel like he thought (the Bills could) beat the Chiefs. The AFC conference is the Chiefs…I think he would rather go with a young quarterback (CJ Stroud)…a new team…instead of staying with the Bills where every year (they’re) getting beat by the Chiefs.”

Diggs helped the Bills to four straight AFC East division crowns during his four-year run with the organization. They only got past the Divisional Round once, however, and even that resulted in a 2020 AFC title game loss to Kansas City.

The Chiefs would also eliminate Stefon Diggs’ Bills in the 2021 and 2023 AFC Divisional Rounds, with both games ending in heartbreaking fashion for Buffalo. Sure enough, the “Wide Right II” game in January wound up being the last straw for Diggs with the Bills.

Diggs now joins an up-and-coming Houston team that stunned everybody by winning the AFC South with a 10-7 record. They went on to defeat the Cleveland Browns in the Wild Card Round before falling to the top-seeded Baltimore Ravens in the Divisional Round.

A Fresh Start Was Necessary For Stefon Diggs

While Diggs put up all-world numbers with the Bills, it was clear that the relationship had run its course on both sides. The four-time Pro Bowler needed a new home, and the Bills were wise to move on before things grew even more tense.

One can also argue that trading Diggs will benefit Josh Allen, who oftentimes got too reliant on No. 14. Diggs’ lack of production in the postseason was also a concerning trend for Buffalo, so this trade allows them to rebuild the receiving corps accordingly.