12. Jerry Reuss - 1988
Jerry Reuss was someone that the White Sox should have avoided.
Jerry Reuss was a very good pitcher in his Major League career. However, at the end of his career, the White Sox made the mistake of bringing him in. After a terrible season in 1987 where he was a part of three different teams, the White Sox decided to bring him in.
He was making $200K coming off a horrid year. The White Sox didn't need to bring in a starting pitcher like that but they were always that team that brought in people that used to be good.
He wasn't as horrible in 1988 as he was the year prior but the White Sox ended up trading him to the Milwaukee Brewers halfway through the year. It isn't a free-agent contract that the White Sox should be proud of.