Eagles' Biggest Offseason Regret Becoming Clear as Losing Streak Continues

Philly's GM is among the best at what he does, but even top executives can make a mistake or two.

There's a good chance that Eagles GM Howie Roseman would like a do-over on this offseason decision. | IMAGN IMAGES via Reuters Connect

Even in a down year, Howie Roseman remains one of the best general managers in football. His Eagles may be 2-3, but the architect of two Super Bowl championships isn't going anywhere.

That doesn't mean he can't make mistakes, of course.

Sustaining a Super Bowl-contending roster for years is never an exact science. The fact that the Eagles have been to three Super Bowls in the last 10 years shows how good Roseman has been, though. Now, as the roster begins to crumble under the weight of injuries and inflated contracts, Philly fans have begun to wonder where the exact tipping point began.

All GMs eventually have some mistakes they'd like to walk back, and for Roseman, the repeated blunder he made this offseason is likely filling him with a ton of regret right now.

Eagles' failure to bolster O-line was a huge offseason mistake

If you ask most Eagles fans, their biggest regret would be the team moving on from offensive line coach and run-game coordinator Jeff Stoutland. The all-time great position coach parted ways with the team after being demoted last season, and the offensive line hasn't really recovered.

Stoutland's genius is well celebrated, but he isn't the biggest regret for the team.

The biggest regret comes from the team's lack of answers along the offensive line from a player perspective.

Since Cam Jurgens was drafted in 2022, the team has not spent a first- or second-round pick on an offensive lineman. That's four draft cycles without a top investment in Philadelphia's most important group. There have been third-round selections, sure: Tyler Steen and current rookie Markell Bell are the beneficiaries there, but the team's divestment at the position has been stark.

Of course, there's a good reason for that. Philadelphia's core of Lane Johnson, Landon Dickerson, Jordan Mailata and Jurgens was supposed to be around for another year or so. Roseman may have thought that would be enough time to get the most out of the championship core.

But the brilliance of Roseman has always been to be one step ahead. Jordan Mailata was brought in years before All-Pro Jason Peters left the team. Landon Dickerson and Jurgens were expected to be picks for the future behind Isaac Suemalo and Jason Kelce.

By staying ahead of the game, Philadelphia's offensive line has managed to stay elite for the better part of two decades. Now, after four years of ignoring the position highly in drafts, the chickens have come home to roost.

There is no set replacement for Jurgens, who has been traded to the Ravens. Philadelphia can hope Bell replaces the now-retired Johnson, but that remains to be seen. Injuries to Dickerson and Steen have also opened up major holes across the line.

The Eagles were absolutely correct in trying to make the most of their championship window. It worked, after all. But in doing so, they ignored investing in the one group that made all their winning possible.

If Roseman regrets anything over the last few years, it's that chief problem the team is currently dealing with.

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