Back in 2019, the Eagles needed to add a speedy receiver that could take the top off of a defense. Howie Roseman decided to reunite with DeSean Jackson, as he traded a 2019 sixth-round compensatory pick in order to acquire Jackson (and a 2020 seventh-round pick) from the Tampa Bay Buccaneers.
The Buccaneers were just trying to dump Jackson's salary and create some cap space, but this trade ended up becoming a big success for the Bucs. They used the sixth-round pick they acquired to select wide receiver Scotty Miller, and Miller has essentially doubled the production Jackson put up since 2019.
After a few subsequent trades, the seventh-round pick the Eagles acquired in this trade was eventually turned into Marquise Goodwin, who opted-out of the 2020 season.
Not only did the Eagles lose the initial trade, but thanks to the trade of Jackson, the Buccaneers were able to allow Chris Godwin to develop into a star receiver, and with the addition of Tom Brady in free agency, he was able to gain chemistry with Godwin and Miller (and Mike Evans) to help Tampa Bay win their first Super Bowl in nearly 20 years. This will go down as a trade that Howie Roseman wishes he could rescind.
