Howie Roseman's four costly decisions are haunting Eagles in 2025

It's Halloween in Philadelphia. But the treats from last season’s Super Bowl have soured. The afterglow of a Super Bowl championship is replaced by the cold, hard light of a new NFL season. Let’s be real. Howie Roseman has been a wizard for years. He’s pulled rabbits out of helmets. His spells have turned late-round picks into Pro Bowlers. But those very spells are now revealing a few cracks in the foundation.

The Eagles hold a respectable 6-2 record. They've made a significant comeback after a two-game losing streak. But is everything clearly alright? Many of the wins have felt more like struggles than statements. But a series of Howie's calculated risks and tough financial decisions is now casting long shadows. The ghosts of departed playmakers are beginning to haunt the halls of the NovaCare Complex. And here are 4 decisions from 2025 that are starting to look like tricks instead of treats.

1. The One That Got Away

Why it hurts: Let’s start with the big man. The Eagles knew keeping Milton Williams would be tough after his Super Bowl performance. However, watching him dominate for the New England Patriots on a $104 million deal is a special kind of sting. Williams immediately became an every-down lineman, setting a career-high with 49 snaps in his Patriots debut.

At the time, it felt like a “nice player, but replaceable” move. Williams was third on the depth chart behind Jalen Carter and Jordan Davis. But fast forward to Halloween, and Williams is playing 66% of snaps in New England, logging 3.5 sacks and six quarterback hits—while the Eagles’ interior depth has been tested weekly.

Position impact: His departure left the Eagles thinner at defensive tackle. Jordan Davis has been terrific. Moro Ojomo has stepped up, sure. But Williams’ explosiveness and stamina are exactly what Philly’s front is missing in late-game situations. The Eagles have had to scramble to replace his productive snaps, and the interior push has not been as disruptive.

2. The Edge That Left

Why it hurts: Josh Sweat was a core contributor to the Eagles' Super Bowl run. He led the Eagles with eight sacks in 2024 and torched Mahomes for 2.5 in the Super Bowl. His reunion with Jonathan Gannon in Arizona on a $76.4 million contract made strategic sense for the Cardinals. However, it cost the Eagles dearly. Sweat has been a primary edge option, racking up five sacks through seven games.

Position impact: Losing Sweat removed a proven, starting-level pass rusher from the equation. His veteran presence and sack production have not been replicated. This loss, combined with Williams' departure, exacerbated a growing depth problem on the defensive front. Meanwhile, Sweat has five sacks in seven games for the Cards.

3. The Trade That Backfired

Why it hurts: March 11, 2025: C.J. Gardner-Johnson, fresh off a six-interception season, was shipped to Houston. They got Kenyon Green in return... a former first-round guard who couldn’t stay healthy or win a job. This trade was a classic high-risk, high-reward move that yielded zero reward. The outcome was a disaster for both sides.

Gardner-Johnson was released by Houston after three games. And he blasted the Eagles on numerous occasions for apparently using him. "Just don’t do them young guys like yall Did me ," he wrote on Instagram. Now he’s in Chicago, still being blunt, still making plays.

Position impact: This created a double-loss. Philly voluntarily gave up a defensive sparkplug and leader in the secondary. In return, they gained an offensive lineman who failed to make the roster. The safety room lost its swagger, and the offensive line gained no meaningful help.

4. The Retirement That Stung

Why it hurts: Finally, Za’Darius Smith. Signed after Week 1 to be the veteran voice in a young edge room, he retired in Week 6. Just like that. No warning. No goodbye tour. Just an Instagram post and a locker full of questions. Smith had 1.5 sacks in five games—more than any current Eagles edge rusher. His retirement forced the Eagles into emergency mode.

Position impact: Smith’s departure created an immediate and obvious short-term need. It thrust younger, less experienced players into larger roles before they were ready. The situation became so dire that the team convinced the retired Brandon Graham to return, a move that screams desperation.

The Cost of Winning Eagles Are Paying

So here we are. The Eagles are 6-2, but the defensive front is held together by grit and BG’s quarter tank. The secondary is young and learning, but without a spark. And Howie Roseman is now watching his 2025 gambles haunt the margins.

Winning a Super Bowl is hard. Repeating? Even harder. And Howie Roseman, for all his genius, is learning that every decision has a shadow. Williams is anchoring a top-10 defense in Foxboro. Sweat is freedom-fighting in the desert. Gardner-Johnson is on his fourth team, still talking, still balling. And Smith? He’s ghosting from a beach somewhere, leaving behind a pass rush that’s running on fumes.

William Faulkner once said, “The past is never dead. It’s not even past.” And in Philly, it’s very much alive, wearing No. 93, 94, 22, and 55—just in different colors.