June 05, 2026
Mitch Stringer/Imagn Images
Number 5 will always love you – even after the Eagles traded him to Washington after the 2009 season.
The Philadelphia Eagles made a blockbuster trade on Monday when they dealt A.J. Brown to the New England Patriots. They have made their share of big trades over the years, so I thought it would be fun to round up their biggest deals this century.
(Note: To make the cut, the trade had to involve at least one established player, not just draft picks.)
OK, so this wasn't a "blockbuster" deal, and Feeley is the least recognizable name of any of the players mentioned in this article, but the Eagles did somehow get a second-round pick for him, and an early two at that, at 35th overall. With that pick, the Eagles selected Reggie Brown, who had a disappointing career.
Some of my younger readers probably don't know how this all went down more than 20 years ago, but Owens was scheduled to be a free agent in 2004, except his agent missed a deadline to file papers that would have voided the final years of his contract. Oops!
Owens wanted to sign with the Eagles (and actually came to an agreement on pay with them), but because of his agent's mistake he was still under the Niners' control. The Niners then traded Owens to the Ravens for a second-round pick, and Owens refused to show up for his physical.
Anyway, yada yada yada, the Eagles, Ravens, and Niners all worked out a settlement that ended up with the Eagles giving a fifth-round pick to the Ravens and Whiting going to the 49ers.
Owens had the best single season by a wide receiver in Eagles history in 2004. In 2005, he got kicked off the team.
Peters was an undrafted tight end who moved to tackle in the pros. He had a couple of All-Pro seasons for the Bills, but a contract dispute sparked trade talks, and the Eagles pounced. The cost for Peters wasn't cheap, but the Eagles' trade for him paid off big-time. Peters started 154 games for the Eagles, and during his prime was one of the best offensive linemen in the NFL, earning six All-Pro nods and nine trips to the Pro Bowl. He'll likely be in the Hall of Fame.
McNabb was traded to Washington for a second-round pick in 2010 and a fourth-round pick in 2011. He played one year in Washington, posting a QB rating of 77.1. He was demoted to the third string by Mike Shanahan before Washington shipped him off to the Vikings for a sixth-round pick the following offseason.
The Eagles didn't parlay the return for McNabb into much. They selected Nate Allen with the second-round pick. The fourth-round pick turned into LB Casey Matthews and a 2012 fourth-round pick, which was used along with another draft pick to acquire LB DeMeco Ryans in a trade with the Texans.
After Kolb was concussed in Week 1 of the 2010 season, Michael Vick had a crazy season in relief. The Eagles then dealt Kolb the following offseason to the Cardinals for a pick and DRC, who was miscast as a slot corner.
After a trade back, that second-round pick became DE Vinny Curry and CB Brandon Boykin.
I can remember when this trade first went down, at the start of the new league year in 2015. It was originally reported that the Eagles got the second-round pick along with Bradford, not the other way around (the second-round pick going to the Rams).
Foles had a 14-4 record the previous two seasons in Chip Kelly's offense, and he was just one year removed from his incredible 27 TD, 2 INT season in 2013. Meanwhile, Bradford had a career 18-30-1 record and had just missed the entire 2014 season with a torn ACL that he had actually already torn once before.
The trade for Bradford, at all, was bad enough. The idea of the team hitching its wagon to this fragile quarterback who hadn't done anything special when healthy was nuts. But when it was revealed that the Eagles had given up the second-round pick along with Foles to make it happen, it became quickly clear that Jeffrey Lurie had made a major mistake giving Chip Kelly full power over the organization.
Kelly's reign of terror continued that offseason, when he just started getting rid of players he didn't like on a personal level. He cut DeSean Jackson and Evan Mathis for no good reason, and he traded McCoy — who had 3,620 yards from scrimmage in two seasons in Kelly's offense — for an average linebacker in Alonso.
McCoy had a few good years in Buffalo; Alonso had one crappy season in Philly.
With Kelly gone, Roseman cooked during the 2016 offseason, and his trade of Maxwell and Alonso accomplished two things:
This was obviously a great trade for the Eagles, but also an absolutely idiotic trade from the Dolphins' perspective.
With Wentz having looked the part in training camp and Vikings QB1 Teddy Bridgewater being lost for the season with a devastating knee injury, Roseman traded Bradford to Minnesota for a couple of picks. The first-round pick (Derek Barnett) didn't pan out like the team would have hoped, but the fourth-round pick (Josh Sweat) has been one of the best Day 3 finds of the Roseman era.
The 2017 Eagles appeared primed for a leap in 2017, but they had one massive hole at cornerback, so they traded Matthews and a third-round pick for Darby, who had 15 pass breakups and 3 INTs in 11 games during the Eagles' first Super Bowl season. (Darby was kind of a sneaky unheralded player on that team, by the way.)
The Eagles traded a third-round pick for Tate at the 2018 trade deadline. He was an eight-game rental (it ended up being a 10-game rental because the Eagles won an atrocious NFC East), and his production (37-342-2 in 10 games) fell short of already tempered expectations. The Eagles' staff admitted that it failed to find an optimal way to utilize Tate's skill set, and he signed with the Giants in free agency the following offseason.
After playing his way into a benching during the 2020 season, Wentz wanted out of Philly, and he got his wish. Roseman did well to salvage good compensation in return, landing a couple of high picks from the Colts, which went a long way toward helping the Eagles get back to the Super Bowl.
Wentz only lasted one season in Indy before he was traded to the Commanders.
Once again finding themselves with a glaring hole at cornerback, the Eagles traded a couple of picks to the then-awful Lions. Slay's tenure in Philadelphia lasted five seasons, three of which resulted in Pro Bowl nods. During his time with the Eagles, he had nine regular season INTs, two of which he returned for TDs, as well as a pair of fumble returns for TDs. He saved some of his best play for the Eagles' Super Bowl playoff run following the 2024 season, when he had 14 tackles, a league-leading 5 pass breakups, and an INT in the Wild Card round against the Packers.
Like Darby above, Slay is a sneaky unheralded player from the Eagles' 2024 championship team.
In four seasons with the Eagles, Brown had 339 catches for 5,034 yards and 32 TDs. During Brown's tenure in Philly, the Eagles went to two Super Bowls, and won one. He made a big impact in a relatively short amount of time and there are many who believe he is the best Eagles receiver of all-time. Meanwhile, everyone involved in Tennessee was fired soon after.
Reddick was a legitimately great player for the Eagles, especially in 2022. Including the playoffs that season, Reddick notched 19.5 sacks and 6 forced fumbles, both of which led the NFL. He was named to the All-Pro team and finished fourth in Defensive Player of the Year voting.
But he wanted out of Philly after he couldn't agree to a contract extension with the Eagles, so he was traded to the Jets for a conditional third round pick that could become a second-round pick if Reddick played at least 67.5 percent of the Jets' defensive snaps and he had 10 or more sacks in 2024. He didn't make it.
That seemed like meager compensation at the time, but ultimately that trade ended up being a disaster for the Jets, as Reddick couldn't agree on a contract there either, so he held out the first seven games of the season. After he did finally start playing again, Reddick had a grand total of 14 tackles and 1 sack in his 10-game career with the Jets.
The Eagles traded a 2026 third-round pick for Phillips at the trade deadline in 2025, and he was a nine-game rental. He was a better rental than Tate above, and the Eagles will get a third-round compensatory pick in 2027 for losing him in free agency this offseason.
We'll see soon enough how the Greenard trade pans out, but the Eagles paid a decent enough price for it to make the cut here.
As noted above, the Eagles traded first- and third-round picks for Brown's best years, and then flipped him on the downside of his career for first- and fifth-round picks. Not including the money paid to Brown, they essentially got four years of Brown's prime years for a third/fifth round pick swap.
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