Chris Archer 6yr/$25.5M (2014)
When it comes to lopsided trades, the Chris Archer deal to Pittsburgh might be the most famous one. In 2018, Archer was traded to the Pirates for ace Tyler Glasnow, Austin Meadows who has been an above average outfielder and Shane Baz who made his major league debut in 2021 and looks to be a main part of the Rays rotation in 2022. However, before this trade was made, Chris Archer was one of the most dominant pitchers in all of baseball.
In a 4 year span from 2014-2017, Archer started 129 games throwing 790.1 innings (leading the league in starts twice), striking out 888 batters and finishing with a 3.63 ERA. Some more stats that show just how dominant Archer was include a 10.11 K/9, 2.94 BB/9 and a 0.98 HR/9. Chris Archer is the textbook definition of buy low and sell high (and then buy low again). Archer signed a 1yr/$6.5 million contract in 2021 with the Rays and currently is a free agent looking for a new team.