Howie Roseman didn’t leave the deadline empty-handed, not by a long shot. Philadelphia wound up turning Cam Jurgens and Jordan Davis into a first-round pick and two second-round picks, a haul that gives the Eagles real ammunition for 2027 and beyond.
But even with that kind of return, there were still a few moves that would have made a lot of sense for Philly. The Eagles had pieces to move, teams around the league had needs, and a few deals could have fit neatly for both sides. Here are four trades that would have had Eagles fans buzzing if they had actually gone through.
One of the cleaner ideas would have sent Arnold Ebiketie to Cincinnati for a 2027 sixth-round pick. Philadelphia has started to get solid edge production from Jonathan Greenard, Nolan Smith Jr., and Jalyx Hunt, which makes Ebiketie feel like a piece they could spare. Moving him would also open the door for rookie seventh-round pick Keyshawn James-Newby to get more snaps late in the season, especially with the Eagles pretty much out of the playoff hunt.
The Bengals, meanwhile, would have gotten a useful rotational pass rusher. Ebiketie has put up 25 tackles, 10 pressures, eight hurries, and two quarterback hits in nine games this year in Philly.
He also would have had a clearer path to more playing time and a chance to compete for a Super Bowl. Of course, the source material also notes that a smart organization would have known the trade could cost Cincinnati a third-round compensatory pick after losing Trey Hendrickson in free agency.
Another move that fits the deadline theme: Riq Woolen to Chicago for a 2027 fifth-round pick. Woolen’s season has been uneven. He has flashed the kind of coverage ability that made him look like the shutdown CB2 tied to his $12 million contract, but the penalties and the big plays allowed have dragged down the overall picture.
For the Bears, the fit is obvious. With Jaylon Johnson and Tyrique Stevenson starting at corner, Chicago still needed someone who could help right away and stabilize the pass defense. Philadelphia would have picked up a Day 3 selection and saved money, while Chicago would have landed a starting corner in a deal that would have helped both teams.
Hollywood Brown is another name that could have been on the move. In this version, the Eagles would send him to Kansas City for a 2027 sixth-round pick. Brown simply hasn’t been involved much in Philadelphia’s offense, logging just five catches for 63 yards and two carries for 12 yards in four games.
The Chiefs have had their own wide receiver issues to deal with. Tyquan Thornton has been on IR, while Xavier Worthy and Rashee Rice have dealt with injuries on and off the field this season. Brown would give Patrick Mahomes a familiar target with plenty of speed, and the Eagles would get a pick they don’t currently have in the 2027 sixth round.
The last hypothetical deal would have moved Landon Dickerson to New England for a 2027 sixth-round pick. Dickerson’s season has been rough by the numbers, with 15 pressures, four sacks, and one quarterback hit allowed in 169 pass-blocking snaps at left guard.
The Patriots have had interior offensive line issues all year, and injuries have only made that worse with Alijah Vera-Tucker and Greg Van Roten on IR. Philadelphia could use the move to clear out a struggling starter and give Willie Lampkin more work at left guard, while New England would get more depth and a chance to plug Dickerson into the starting lineup.
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