Howie Roseman, Eagles gamble on team chemistry could cost them this offseason

Howie Roseman is nothing if not calculated. The Eagles’ GM always seems to be playing three moves ahead, but this offseason, he’s walking a very fine line.

The Eagles didn’t extend any of their impending free agents during the 2024 season—not because they couldn’t, but because they chose not to.

It’s the same approach they took in 2022, when they made a Super Bowl run, and Roseman made it clear at Super Bowl Opening Night that it was by design:

“Once you start doing that, it’s almost like, are you picking favorites?” Roseman said. “And the other guys start saying, ‘What about me?’ And they start playing for themselves as opposed to the team.”

Howie Roseman’s logic is pretty clear.

The idea is to keep the locker room together and avoid any contract drama so the team and staff can focus on the bigger picture. Obviously, “keeping the main thing, the main thing” worked with the team completely locked in and ready to play the Kansas City Chiefs in Super Bowl LIX on Sunday.

There is a certain level of risk with the strategy as well, but Howie Roseman is very self-aware that his stance on in-season contract extensions and/or negotiating could cost the Eagles this offseason.

Zack Baun, Mekhi Becton, Milton Williams & Others Set To Test Free Agency:

The Eagles have some serious decisions to make in March when free agency opens. Several key contributors are set to hit the open market, including:

Zack Baun – From special teams signing to All-Pro linebacker. The Eagles brought him in on a one-year, $3.5 million deal with no expectations beyond depth and special teams work. Instead? He became the best linebacker in the league. The Eagles need to keep him, but they could’ve extended him for a fraction of what he’ll now command.

Mekhi Becton – Once a draft bust, now a legit starting lineman. The Eagles took a low-risk flyer on him post-draft, hoping he could be a swing tackle at best. Instead, he locked down right guard and played his way into a multi-year deal. His value is way up—and that means Philadelphia might not be able to afford him.

Milton Williams – A quiet but vital piece of the defensive line. The Eagles love their defensive line depth, and Williams proved to be one of the most versatile linemen in their rotation. But young, productive pass rushers always get paid, and Williams is now in line for a payday elsewhere.

Other free agents like Josh Sweat, Kenny Gainwell, and Isaiah Rodgers could also get offers, making this an offseason where Howie Roseman has to thread the needle carefully.

Did the Eagles Cost Themselves Money?

The front office gamble is definitely still in-play. It’s not hard to see that by locking in Baun, Becton, or Williams to new contracts earlier this season could have saved them millions. Now, it looks like all three likely played themselves into bigger contracts and will now have a very busy free agency period fielding offers.

Howie Roseman acknowledged that risk last night in New Orleans:

“I’ll do anything for a championship,” Roseman said. “So if that’s the trade-off and maybe we lose a player, I won’t like that, but I’ll take it.”

Of course, that’s much more easier to say when you’re preparing to play in the Super Bowl, but when free agency opens, reality will hit hard.

What’s Next?

Howie Roseman isn’t afraid to make aggressive moves, but the reality of the situation is that the Eagles can’t keep everyone.

Priority #1: Zack Baun. He transformed their defense, and losing him would be a disaster.
Priority #2: Milton Williams. D-line depth is always an important piece to any defense.
Priority #3: Mekhi Becton. Roseman values versatility on the O-line, but with other needs, he may have to let Becton walk.

Right now, nothing else matters outside winning a Super Bowl and parading down Broad Street with the Lombardi Trophy next week.

We can worry about the contract negotiations this Spring, but it’s definitely something to keep an eye on as Howie Roseman and the Eagles attempt to keep a solid core intact.

The decision-making will definitely come back to bite them. How badly, is up for debate.

All Things Philadelphia Eagles Here >>

Join The Chase