1. 1985 - Jerry Rice
Merely looking at the numerics, the Patriots' trade with the 49ers during the 1985 NFL Draft was fairly even. New England gave up the 16th overall pick in exchange for the 49ers' 28th and 56th overall picks (the teams also swapped third-round picks). It appears a fair deal for both sides, until you look at whom the 49ers traded up to select - Jerry Rice.
Then-49ers coach Bill Walsh was captivated by the Mississippi Valley State wide receiver and traded up to obtain the 16th pick in the draft for fear that the Cowboys were going to select Rice with the 17th pick. With Rice the 49ers landed the greatest receiver in the history of the game. By the time Rice retired he owned the career records for receptions, receiving yards and touchdowns - and no one is going to come close to any of those records anytime soon.
What did the Patriots do with the picks they got in exchange? They drafted Trevor Matich and Ben Thomas. In comparison to one of the greatest to ever play the game, that’s not much of a consolation prize.