No. 6: Three-team trade between the White Sox, Dodgers, and Reds - December 2015
This deal had so many moving parts that it needed its own trade graph.
Yes, you are reading that right. The White Sox traded away Frankie Montas, an eventual top-of-the-rotation talent, for Todd Frazier.
To be clear, the loss of Montas is the sole reason why this deal is so high up on this ranking. Johnson is now out of the league after being worth -0.9 bWAR in parts of three big league seasons.
Thompson, now 32, is still active and is projected to make the Dodgers' Opening Day roster. He has been around the league for six years now, bouncing around between multiple different clubs, but has never had as big of a shot at everyday playing time as he does in 2023.
The White Sox moved on from him after he hit five home runs with a .295 average and 147 OPS+ in 2015.
Montas, now a member of the New York Yankees, made just seven appearances for the Sox before he was sent packing in favor of Frazier. Of course, after the deal went down he emerged as an ace-level pitcher for the A's.
He went on to play six years in Oakland, posting a 3.70 ERA in 114 appearances with a 111 ERA+. He's one of a few future star pitchers that the Sox let go of too early.
To Frazier's credit, he waited until he joined the White Sox to start displaying the best power numbers of his career. He hit 40 home runs in 2016 and drove in 98, both career highs, but he was a part of such terrible White Sox teams that his production did nothing to help the club succeed.