1. Having Tony La Russa as their manager
It’s not a secret that Hall of Fame manager Tony La Russa was far from being the manager that he used to be.
La Russa hadn’t managed in a decade but White Sox owner Jerry Reinsdorf made a rookie mistake that a businessman of two years (let alone of Reinsdorf’s experience of 60 years and 40+ years in sports) would never make: mixing business and personal ventures.
Reinsdorf has said that his biggest regret as White Sox owner was firing La Russa during the 1986 season. Instead, he hired La Russa who hadn’t managed in a decade, was behind the times in nearly every aspect of the game, and didn’t relate to the players in much of anything (if anything at all, which partially lead to their lack of motivation this season as mentioned in no. 2), made numerous managerial gaffes including intentionally walking batters when they had two strikes against them, and, now, La Russa’s health was put at risk or at least exacerbated by managing again.
Now, Reinsdorf may have a regret bigger than firing La Russa more than 35 years ago: rehiring him.