No. 9: Todd Frazier, David Robertson and Tommy Kahnle to the New York Yankees for Blake Rutherford, Tito Polo, Tyler Clippard and Ian Clarkin - July 2017
Yet another massive trade involving multiple longtime veterans and a whole lot of prospects. Just like the White Flag Trade, this one did not work out for the Sox.
Frazier, Robertson, and Kahnle all had established themselves as stars prior to joining the White Sox and each of them was expendable once the awful 2017 season began to unfold. This is another one that's hard to blame Rick Hahn for trying, but the return was just atrocious for the club.
As a matter of fact, only one player acquired by the White Sox in this trade played a single inning in the big leagues for them. Clippard, one of the more durable and respected relievers in the game, posted a 1.80 ERA in 11 games before being flipped to the Astros less than a month later.
Clarkin was supposed to be a solid left-handed starting pitcher but he struggled to stay consistent while in the Sox system and never made it past Double-A for the club.
Polo, a speedy outfielder, also struggled to find consistency in the organization. His only full year for the Sox was in 2018 when he made 53 appearances, registering 47 hits but just 13 extra-base hits. His average that year was .254 and he was cut loose at the end of that year.
Rutherford actually stayed in the system until the end of the 2022 season. He displayed occasional promise in his rise through the organizational ladder but he had a hard time with strikeouts and spent two seasons in Triple-A before becoming a minor league free agent at the end of the year.
He recently signed a minor league deal with the Washington Nationals, officially putting an end to this trade tree and cementing its place as one of the worst ever by the Sox.