Howie Roseman got his revenge in 2018. The Eagles GM—who was effectively demoted in 2015 in favor of head coach Chip Kelly—hoisted the Lombardi Trophy two years after Kelly was fired by Philadelphia.
But as the Eagles prepare for their third Super Bowl appearance in the last eight years (including their second in the last three), Roseman’s resurgence is not simply a reclamation story. He has built a juggernaut in Philadelphia, one that has the NFL’s second-best regular-season record over the last three years, behind only the Chiefs, and that should remain competitive for years to come.
Roseman is a salary cap magician who used every possible loophole to ensure sustained success for the Eagles. His favorite trick was the use of void years—which stretch a player’s cap hit past the seasons included in his contract—to ensure additional cap space in the short term.
Void years can be found in the contracts of many of the team’s stars, including MVP candidate Saquon Barkley, who was signed this offseason. Barkley inked a three-year, $37.75 million deal with void years from 2027 to 2030, which leaves a potential $19.3 million cap hit for the Eagles in 2027 if he doesn’t re-sign. However, his cap hit this season was just $3.8 million, which allowed them to sign other major free agents, including Defensive Player of the Year nominee Zack Baun.
Roseman also restructured several contracts with veteran players, including cornerback Darius Slay two offseasons ago. The Eagles nearly released the six-time Pro Bowler, but instead gave him a $6 million raise in guaranteed money and added void years to his deal.
Philadelphia has also hit on its draft picks in recent years, including Jalen Carter (No. 9 in 2023), Quinyon Mitchell (No. 22 in 2024), and Cooper DeJean (a second-round pick—40th overall—in 2024). The latter two are nominated for this season’s Defensive Rookie of the Year award. Hitting on draft picks gives teams competent players on rookie-scale deals, and allows for flexibility down the line when some stars age out (i.e., Mitchell and DeJean taking over for 34-year-old Slay).
Future Regret?
The risk of stretching out contracts and adding void years is limiting future flexibility. The Eagles were just 19th in the league in cap allocation this year, but already have the largest number every season from 2027 to 2030, per Spotrac.
While this could come back to bite Philadelphia down the line, many of the players it has locked up for multiple years are in their prime. This means their competitive window will likely last beyond this recent three-year stretch. Roseman also has proved he can be shrewd with his roster moves, which may need to include moving on from some stars in the coming years to make space. Lastly, the NFL salary cap has increased by between 7.7% and 14% in each of the last four years. Future years are expected to have additional space.
Ultimately, a Super Bowl win this season may be worth any future pain for the Eagles front office, and give them some leeway against potential criticism from one of the country’s most infamous fan bases.
