No. 1: Fernando Tatis Jr. and Erik Johnson to the San Diego Padres for James Shields - June 2016
As if there could possibly be another entrant to top this list.
Shields, the longtime ace of the Tampa Bay Rays and Kansas City Royals, was in the middle of his second season as a San Diego Padre before this beast of a trade went down. He had been struggling to start the 2016 season, so the White Sox's interest here was curious from the start.
In a White Sox uniform, the player formally known as "Big Game James" made 77 appearances with a 16-35 record and a combined 5.31 ERA. His 79 ERA+ was well below average and he saw his strikeouts go down, home runs go up, and walks go up as well. He was awful in every way for a team that was just as awful.
Johnson, a starting pitcher himself, never amounted to much at the major league level. He made appearances for both the White Sox and Padres in parts of four years with a combined 5.28 ERA and 76 ERA+.
Then there's Tatis, one of the top young players in the league. Unfortunately for all fans of the game, he has struggled with injuries (that were his own doing off the field) and he's missed significant time in each of the past four years, including the entirety of the 2022 campaign.
When he's on, Tatis is at or near the top of the league in overall production. In 2021, his only full season, he hit a league-leading 42 home runs with 97 RBI, 25 stolen bases, a .282 average, and an OPS+ of 166. He finished third in the NL MVP voting that year but he will surely earn multiple trophies down the line.
While some may say that Tatis' 14-year contract extension is already an albatross for the Padres, it feels too early to slap that label on it. If he can get healthy and stop getting into accidents off the field, he has a very real shot at a Hall of Fame career. Even if he never played another game at the big league level, his production would outmatch Shields' in a White Sox uniform.