Stefon Diggs was shockingly traded away to the Houston Texans by the Buffalo Bills during the 2024 NFL offseason. This ends a four-year run where he was one of the most productive wide receivers in the entire league. He also helped the Bills become annual Super Bowl contenders.

It’s unclear exactly why Diggs was traded, but many rumors have circulated that he has been unhappy with his situation in Buffalo. Some rumors have suggested that he may not have been on the same page as Josh Allen, but former wide receiver DeSean Jackson believes he wanted to leave for a different reason. He discussed this during a recent episode of the “Up & Adams” show.

"(Stefon Diggs) didn't think they could beat the Chiefs." @DeSeanJackson10 gives some insight on why he thinks Stefon Diggs wanted out of Buffalo 👀@heykayadams pic.twitter.com/f51UAUIEX1

— Up & Adams (@UpAndAdamsShow) April 4, 2024

“I wouldn’t say that they weren’t seeing eye to eye, it was just more of him wanting to win I think,” Jackson said. “I don’t feel like he thought that they were going to be able to beat the Chiefs. The AFC Conference is the Chiefs, and I think that he would rather go with the young quarterback, and a new team that’s thriving instead of staying with the Bills, where they are getting beat every year by the Chiefs … We’ve seen it year after year.”

The Buffalo Bills have made a Super Bowl appearance with Stefon Diggs on their roster despite making it into the NFL playoffs every year. DeSean Jackson pointed out that they have been unable to get past Patrick Mahomes’ Kansas City Chiefs, who have won a ring in each of the past two seasons.

Jackson believes Diggs desires to win a ring of his own, and he would have a better chance of doing so with a different team. He finds himself in a good situation to potentially do so with rising star CJ Stroud. The Houston Texans advanced to the second round of the playoffs last year, so adding Diggs and a strong cast of free agents could help them take the next step.

Stefon Diggs’ record against Chiefs in NFL Playoffs

During his four years with the Buffalo Bills, Stefon Diggs faced off against Patrick Mahomes’ Kansas City Chiefs three times during the playoffs. Unfortunately for the Bills, the Chiefs went undefeated in those three games. They twice occurred during the divisional round, with the third taking place in the AFC championship game.

In addition to losing all three, Diggs was relatively unproductive during those games. He combined to record just 12 receptions for 105 yards and zero touchdowns in the three matchups. This could potentially be why he has been frustrated with his situation on the Bills, as Jackson recently suggested.