Perhaps the biggest swing and miss in the Manny Machado sweepstakes came from the windiest of cities, a franchise whiffing on a myriad of things the last decade and a half: the Chicago White Sox.
Machado’s record 10-year, $300 million deal with San Diego on Tuesday left the Sox and its fanbase in a sour mood, and with good reason. Since winning the World Series in 2005, seemingly nothing has gone right for the South Side of Chicago.
The White Sox have been to the playoffs just once in the last 13 seasons. They haven’t finished over .500 since 2012. The closest they’ve come to winning the AL Central in the last six season was 2016 when they finished 16.5 games back of Cleveland. The rival on the north side of town has been to has straight playoffs and is trending towards a fifth.
Chicago South even went the creative route in recruiting Machado, trading for his brother-in-law Yonder Alonso and best friend Jon Jay.