1. Adam LaRoche - 2015
White Sox fans won't soon forget Adam LaRoche's tenure in Chicago.
Adam LaRoche actually had a really nice Major League career. He was a Gold Glove-caliber first baseman in his career in addition to making an impact with his bat pretty much everywhere he went.
The only team he was terrible with was the Chicago White Sox. He signed with them and made 12 million dollars to have a 0.8 WAR. He was literally a terrible player during the 2015 season.
Following that, he cause a locker room stir that caused a debate league-wide. Even the national sports media scene got in on this debate. He ended up retiring early, less than a month before the 2016 season started because some White Sox players didn't love that he had his kid there every day.
Some of these contracts are worth laughing at and some of them are enough to make any White Sox fan incredibly mad. There will be more over time but we can only hope they are fewer and farther between.