Chicago White Sox
Win decline: -34
The 1921 White Sox put an interesting twist on the whole lose-your-players-because-you-won't-pay-them bit. The players decided to make a little freelance money fixing the 1919 World Series, which, of course, resulted in the famous Black Sox Scandal, which first affected the team in the final week of the 1920 season and really hit hard in 1921. Key players got banned from baseball and 62-92 happened.
(The Bears are on the NFL list and the Bulls on the NBA list. Volatility, thy name is Chicago sports.)