No. 10: Nick Madrigal and Codi Heuer to the Chicago Cubs for Craig Kimbrel - July 2021
It's hard to blame Rick Hahn for making the attempt here. After all, Kimbrel is one of the best relief pitchers in the history of the game.
The only thing questionable about this is the fact that he wasn't acquired a few years sooner. Kimbrel had been in the midst of a rough two-year stretch before re-emerging as a dominant closer on the Cubs prior to the trade.
The then-33-year-old had allowed just two earned runs in 36+ innings of work for the Cubs, good for an ERA of 0.49 and ERA+ of 865. Yes, he was 765 percent above league average to start the year.
With the White Sox, he made 24 appearances and stumbled to the finish line with a 5.09 ERA and 87 ERA+ across 23 innings of work. He looked much more like the 2019 and 2020 versions of himself than he did in his Braves days.
Madrigal was the big piece going from Chicago to Chicago here, as he was the No. 3 prospect in the White Sox system in 2021 per MLB.com. He had performed well with the Sox in 83 games prior to the trade, posting a .317 average and 109 OPS+ while sitting around average on defense.
With the Cubs, he doesn't seem to have a spot on the active roster, so his potential is very much being wasted. Instead, Heuer is going to end up being the piece the White Sox will miss the most.
He had shown some flashes of brilliance before the trade and he did struggle to start his Cubs tenure, but he looked like the real deal last year.
In 25 appearances last year, Heuer posted a 3.14 ERA and 136 ERA+ across 28+ innings of work. He was supposed to be a key contributor out of the Cubs' bullpen in 2023 but he is recovering from Tommy John surgery and is likely going to miss (at the very least) half of the upcoming season.