When news broke that Jeff Stoutland would no longer be a member of the Philadelphia Eagles' coaching staff, it marked a true end of an era for one of the longest-tenured assistants in Philly history.

Initially joining the Birds under Chip Kelly after a successful tenure at Alabama, Stoutland outlasted both his first boss and his predecessor, Doug Pederson, before being promoted to run-game coordinator under Nick Sirianni. Stoutland helped to turn Jordan Mailata from an oversized rugby player into a Pro Bowl left tackle, established Philly as the best offensive line in football, and even played a major role in Saquon Barkley's 2024 season, which will go down as the best individual run in franchise history.

Talking about his exit to Nick Foles on his The SZN podcast, Stout revealed when he knew it was time to close down Stoutland University, as, after over 40 years coaching, he simply knew it was time.

“I’ve done this for a very long time, as I’ve said, 30 years in college, 13 years in the NFL, so a lot of players will ask me along the way, ‘Hey coach, can we talk?’ or whatever. And they have the thought of maybe not playing football in college any longer, or if a guy is thinking about retiring in the National Football League. So I’ve had these conversations with players. I always say, ‘Look, I can’t tell you what you should do or are going to do. I have no idea. That’s not right for me to say that.’ But I always say this: ‘I think there’s some point in your life where you know. You kind of just know.' I think I reached that point,” Stoutland said via John Clark.

“I was in a position where a lot of things changed, things were happening, things had taken place. And I’m like, ‘Wait a second, this is what I talked to the other players about all the time.' I just felt like it was that time. I haven’t looked back since. I know there’s things that I’ll miss, but I know there’s going to be some exciting things going forward, and opportunities and challenges, and that’s kind of what I’m all about.”

Will the Eagles miss Stoutland in 2026? Most certainly so. Even if Mannion is looking to change things up in the trenches under new offensive coordinator Sean Mannion, embracing more power concepts to go with an increased focus on wide outside runs of the tackles, Stoutland is one of the very best teachers to ever coach the offensive line, and leaves very big shoes for Chris Kuper to fill in the role moving forward.