Landon Dickerson had the world at his fingertips two years ago with a landmark contract extension that made him the highest-paid guard in NFL history. But only two years after becoming the NFL’s highest-paid guard, the season took a toll on his body, forcing him to choose between his health, his wallet, and his future in Philadelphia.

“The Eagles and three-time Pro Bowl OG Landon Dickerson have agreed to a revised two-year contract at around $36M, per sources,” ESPN senior NFL reporter Jeremy Fowler reported on March 12.

With the restructuring now official, Dickerson will earn $36 million over the next two seasons. That figure is roughly $3 million less than the $39 million he was originally owed for the 2026 and 2027 seasons combined.

That previous deal came in March 2024, when Dickerson signed a four-year, $84 million extension with the Eagles. At $21 million per year, the contract made him the highest-paid guard in league history at the time, surpassing Chris Lindstrom’s $20.5 million per year. It was a reward for three years of anchor-level play on one of the most dominant offensive lines in the league.

That extension was set to run through the 2028 season. But with the revision, that timeline no longer holds. Dickerson’s contract will now expire after 2027, meaning his ties to Philadelphia beyond that year have been voided, per Fowler. For the 2026 season specifically, Dickerson is set to earn $15.7 million.

This extension comes after what Dickerson went through physically in the last season. During the Eagles’ August 10 public practice, Dickerson went down clutching his right knee and was carted off to the locker room. The sight of that shook the entire locker room.

“It was kind of scary when he got hurt,” Eagles right guard Tyler Steen said back then. “Just seeing him the next few days after that, seeing that he was in good spirits, and knowing that he was eventually going to come back, and seeing him back out there, was pretty encouraging.”

However, Dickerson underwent surgery for a meniscus tear and rehabbed at a remarkable pace, returning in time for the Eagles’ regular-season opener against the Cowboys. It looked like the worst was behind him. But the season had other plans.

In Week 5 against the Broncos, Dickerson suffered a left ankle injury that forced him out of the following week’s game against the Giants. Between the meniscus surgery, the ankle, and a back issue that surfaced mid-season, Dickerson wrapped up 2025 with a career-low 836 snaps across 15 games. 

For a player of his caliber, that number underscored just how much the season had cost him physically. And that’s why, by February, retirement speculation had become a genuine conversation around the league.

That speculation is now firmly in the rearview mirror. But Dickerson’s restructure wasn’t the only financial move the Eagles made heading into this offseason. 

Landon Dickerson’s deal is just one piece of the Eagles’ cap puzzle

When the league announced the 2026 salary cap would exceed $301.2 million, the Eagles were already in a decent position. Philadelphia entered the offseason with approximately $13.76 million in cap space. But general manager Howie Roseman, known for engineering cap relief in creative ways, wasn’t done. He moved quickly to create additional flexibility before the league year opened.

A major move involved Jordan Davis. The DT agreed to a three-year, $78 million extension with $65 million guaranteed. At $26 million per year, he became the second-highest paid interior defensive lineman in the league behind Chris Jones. But beyond the headline number, the deal served a direct cap purpose for Philly.

“Before this deal, Davis was set to count $12.94 million against the salary cap while playing on his fifth-year option. With the extension, the Eagles can now spread the salary cap hit over a longer period and reduce Davis’ charge against the cap,” The Athletic’s Zach Berman noted.

In plain terms, the Eagles converted what would have been a large, single-year charge into a more manageable number spread across multiple seasons. Another move involved Michael Carter II. 

Carter arrived via trade from the Jets in October 2025. But struggled to find his footing with the Eagles, finishing with just 10 tackles in eight games. He was still tied to the three-year, $30.75 million contract he had signed with New York. And that carried a projected $10.12 million cap hit for this year. 

Rather than cutting Carter loose, the Eagles renegotiated his deal. That lowers his cap number and keeps a serviceable back on the roster at a more manageable price. Together, these restructures are giving Roseman the financial flexibility to pursue upgrades on both sides of the ball, whether through free agency signings, trades, or the draft.