The draft card was already filled out. TCU wide receiver Jalen Reagor, 21st overall pick, Philadelphia Eagles. In his home during the COVID-19 pandemic, Howie Roseman probably felt that familiar flutter of confidence that comes with making what you believe is the right choice. One pick later, the Minnesota Vikings would select Justin Jefferson from LSU and everything would change for both teams.
That April evening in 2020 would come to define the lowest point of Roseman's career as Eagles general manager. This week, when Bleacher Report's Matt Holder named Reagor the NFL's "Worst First Round Pick" of the last five years, it served as a stark reminder of just how bad that decision looked. Yet four years later, as confetti fell at Super Bowl LIX and the Eagles celebrated their 40-22 victory over the Kansas City Chiefs, that same mistake had somehow become the foundation of Roseman's greatest success.
The pain wasn't just in what Philadelphia got, but in what they missed. While Reagor struggled to stay healthy, managing just 31 catches for 396 yards as a rookie, Jefferson was breaking records with 88 catches for 1,400 yards and earning All-Pro honors. The gap only got worse. Reagor's entire two-year Eagles career produced 64 catches for 695 yards. Jefferson's worst season still had 68 catches for 1,074 yards in just 10 games.
But hidden in that same draft was a decision that would save Roseman's career. Just 32 picks after the Reagor selection, with the 53rd overall choice, Roseman took a chance on Oklahoma quarterback Jalen Hurts. It seemed odd at the time, drafting a quarterback when Carson Wentz was supposed to be the franchise player. Critics questioned why they needed the pick. But sometimes the best decisions don't make sense to anyone else.
The 2020 season became a disaster that proved every critic right. The Eagles stumbled to a 4-11-1 record, their worst finish since 2016. Wentz played so poorly that by December, Hurts was getting his first NFL starts. What looked like desperation was actually the first glimpse of Roseman's salvation. When the Eagles finally traded Reagor to Minnesota for a fifth-round pick in 2022, it stung. They were giving their first-round bust to the very team that showed them what the right choice looked like. But by then, Hurts had the keys to the franchise and everything was changing.
Rather than hiding from his failure, Roseman got aggressive. The 2021 season marked the real start of his comeback, as Hurts became the full-time starter and began showing flashes of greatness. The Eagles made the playoffs for the first time since 2018. The 2021 draft became another statement when Roseman selected Alabama's DeVonta Smith with the 10th overall pick. This wasn't playing it safe after the Reagor disaster. This was betting big on another receiver, knowing another miss might cost him his job, while building around the quarterback he'd quietly found in that same 2020 class.
Smith played well right away, but Roseman wasn't done. In April 2022, he made the trade that defined his career, getting A.J. Brown from the Tennessee Titans for the 18th and 101st picks. The move was risky, giving up valuable draft picks for a player who would need a huge contract right away. The Eagles gave Brown a three-year, $96 million deal before he played a single snap in Philadelphia.
The 2022 season proved Roseman right. The Eagles started 8-0 for the first time ever, with Hurts and the new offense clicking immediately. They finished 14-3, then destroyed the Giants and 49ers by a combined 69-14 to reach Super Bowl LVII. Though they lost to Kansas City 38-35, the foundation was clearly strong.
Then came 2023 and Roseman's biggest test yet. After losing both coordinators to head coaching jobs, the Eagles started 10-1 and looked unbeatable. But then everything fell apart. They lost five of their last six regular season games and got embarrassed 32-9 by Tampa Bay in the playoffs. Critics started questioning everything again. Had Roseman just gotten lucky? Was the Super Bowl run a fluke?
Here's what made Roseman different from other GMs facing similar problems: he didn't panic. Instead, he made smart changes, hiring defensive coordinator Vic Fangio and offensive coordinator Kellen Moore. More importantly, he figured out what the team really needed—a dynamic running back who could take pressure off Hurts and help the passing game.
Enter the 2024 masterstroke: signing Saquon Barkley away from the division rival New York Giants. The move shocked everyone and paid off immediately. Barkley didn't just succeed; he made history, rushing for over 2,000 yards and becoming just the ninth player ever to reach that milestone. With Brown continuing his All-Pro play and Smith staying consistent, Roseman had built the most explosive offense in team history.
The 2024 season became complete vindication. The Eagles finished with 18 total wins, tying the NFL record. They scored a playoff-record 145 points on their way to the championship, finishing with a dominant 40-22 victory over Kansas City in Super Bowl LIX. This wasn't just redemption; it was a masterclass in building a team.
What makes Roseman's story so impressive isn't just that he fixed his mistakes—it's how he handled each challenge. Not every move worked perfectly. Some coaching hires struggled and several free agent signings didn't pan out. But his success rate on big decisions has been remarkable. Beyond the headline moves, he's consistently found value in later draft rounds and smart veteran signings. The Barkley signing was brilliant not just for what it accomplished, but for when he did it—taking advantage of a rival's mistake while filling a crucial need.
The man who once faced potential firing after a disastrous draft pick now sits at the top of the NFL, his methods proven by the ultimate prize. It's a turnaround that shows the power of learning from failure, of responding to embarrassment with determination and of never letting one mistake define an entire career.
The draft card that once represented rock bottom somehow became the first chapter in a redemption story that ended with the Lombardi Trophy. In a league where careers can end with a single bad decision, Howie Roseman turned his worst moment into his greatest triumph.