They Laughed at Him Five Years Ago, Now He Runs the NFL
They doubted him, mocked him, even called him the worst. Now he’s proving every critic wrong.
If you’ve been following Sports Square for a while now, you know what emphasis I put on General Managers. I personally think that if a team doesn’t have a good GM, the team sucks. They won’t bloom. That’s kind of been my motto from day one.
Since we’re in 2026 and the NFL landscape has changed a lot since the last time I did this, I thought, why don’t we rank the General Managers again?
So I’m beginning this series by talking about who the best GMs really are. We’re starting with the NFL, then we’ll make our way to the NBA next week, and the MLB the week after that. In the middle or at the end of it all, we’ll finish it up with a roundup where the people speak.
Let’s begin.
Howie Roseman is the best GM in the NFL right now, if not the best GM of all time.
He’s Already Got Championships
First, let’s get this out of the way: the Eagles just won Super Bowl LIX, beating the Chiefs 40‑22 in a game where Philly imposed its will early and never let Kansas City back in it. Cooper DeJean had a pick-six on his birthday, Jalen Hurts was named Super Bowl MVP, and the defense dominated throughout the game.
That alone changes the narrative. Winning a Super Bowl is the only thing that actually matters in this league. You can talk contracts and drafts all you want — but when your roster actually hoists the Lombardi Trophy, you’re not just guessing anymore.
Roseman now has two Super Bowl titles with the Eagles, and he’s one of only a handful of GMs to win multiple championships with different head coaches and quarterbacks since the salary cap era began.
QB Contracts Aren’t His Strength, But They Work
I don’t think Roseman should get credit for finding quarterbacks or their contracts. That’s always been a weak spot for him. One of the biggest examples of this was Carson Wentz. Finding Wentz wasn’t a big deal, but extending him to that four‑year, $128 million contract with over $107 million guaranteed was pretty bad. In fact, it would have kept him in Philly through the 2024 season and almost sank the organization.
Many thought the Jalen Hurts deal would be the same story. A huge contract with tons of guarantees made people think it was another repeat of the Wentz situation.
Instead, Hurts delivered. A Super Bowl MVP and the face of a championship team. That changes the narrative on Howie’s quarterback record in a big way.
Drafting and Player Development
What makes Howie the best isn’t just one part of the job; it’s doing everything at a high level.
Yes, he’s had a lot of draft busts. Jalen Reagor, Derek Barnett, Sidney Jones, JJ Arcega‑Whiteside, and Davion Taylor are names people still remember.
But we aren’t talking about Howie from 5 years ago. We’re talking about the Howie Roseman of the last few years, who drafted guys like:
Cooper DeJean: All‑Pro rookie, Super Bowl interception for a touchdown on his birthday.
Quinyon Mitchell: Defensive starter and impact cornerback.
Jalen Carter: Pro Bowl interior DL and game changer.
DeVonta Smith: Big-play receiver who consistently makes defenses pay.
Landon Dickerson: All‑Pro lineman signed long-term.
Those are foundation pieces right there.
And here’s a big piece people overlook: even the guys he didn’t hit on in Philly often stick in the league and succeed somewhere else. That tells you the evaluations aren’t random. They just don’t always fit in Philly.
Trades and Additions
If drafting is Howie’s hammer, then trades are his chisel.
Roseman moved up for DeVonta Smith. He stole A.J. Brown and made it work. He brought in big playmakers like Saquon Barkley, who went on to set a franchise single‑season rushing record and then signed a historic extension, making him the highest‑paid running back in NFL history.
And let’s not forget Haason Reddick, Bradberry, and guys who have brought real value on both sides of the ball over the last few years.
How does he keep getting away with this?
Cap Management and Strategy
Another one of Howie Roseman’s biggest assets is his salary cap technique.
He’s aggressive with extensions and restructures, keeps costs down early in player careers, and creates flexibility that most GMs dream of. This is the reason Philly could build one of the most expensive offenses in football and still field a title contender.
We’re talking big money at quarterback, running back, two elite wide receivers, tight end, and three starting offensive linemen, and it still worked on both sides of the ball. That’s scheming, not luck.
Long Tenure and Influence
According to multiple sources, a GM job only lasts about three years in the NFL. Howie Roseman’s already been running the Eagles’ roster for over a decade, building multiple contenders and two champions along the way.
The Eagles aren’t the most successful franchise in history, but they have a GM who can:
Draft young studs
Pick up big free agents
Swing trades whenever he wants
Work the cap better than most people realize
That’s the point of this series. GMs should be valued a lot more than they are, because they are the masterminds behind who actually plays on the field.
If We’re Ranking the Top 3 NFL Executives
Howie Roseman (Eagles)
Les Snead (Rams)
John Lynch (49ers)
Les Snead somehow puts together a complete team every year and brings the Rams to the playoffs every single time. The Rams once again have a very good chance to make it to the Super Bowl this year.
John Lynch hasn’t won a Super Bowl yet, but he’s gone to multiple big games, always pushes the market in free agency, and has kept the 49ers competitive year after year. He’s pretty good at finding backups, I’ll say that.
As you can probably tell, the change from last year is at #2. It was Brett Veach last year. This year, it’s Les Snead. The 49ers couldn’t even make the playoffs last year, which is why Snead was able to get up to 2.
Thanks for reading this one, everyone!
Well written. A top 10 and a bottom 5 would be cool reading as well.
We'll see them next week.