No. 15: Melky Cabrera and cash traded to the Kansas City Royals for A.J. Puckett and Andre Davis - July 2017
By the time Melky Cabrera came over to the White Sox, he had already wrapped up his prime years in Major League Baseball.
A switch-hitter who saw some extreme highs and lows throughout his career, he signed a three-year, $42M contract heading into the 2015 season and gave the Sox a veteran presence to help guide the team through some rebuilding years.
He was actually still a pretty great hitter when he was with the Sox, as he hit 39 home runs in 407 games with a .287 average and 108 OPS+, so he did exactly what the club wanted him to do.
However, it's the package the White Sox got in return for the longtime veteran that warrants a spot on this list.
Chicago sent Cabrera packing to the division rival Kansas City Royals, even including $2.5M in cash to help the Royals with the financial part of the deal. Neither of the two pieces heading from the Royals to the Sox ever even made the major leagues.
A.J. Puckett, now 27, played in a total of five games at the White Sox's High-A affiliate before going M.I.A. for two years thanks to Tommy John surgery.
He was selected by the Atlanta Braves in the minor league Rule 5 Draft in December of 2020 and wrapped up his White Sox tenure with 27 innings to his name.
Andre Davis, the other pitcher moving from Kansas City to Chicago, made just four appearances for the A-ball Kannapolis Intimidators, posting a 2.84 ERA over 12.2 innings before never playing another inning in professional ball, making this trade a total dud.