As a Red Sox fan, I'll never get over the signing of Matt Young in 1991. Going into the '91 season, he had the worst won loss percentage of any pitcher in history with as many decisions as he had. Every team that had previously signed him paid him a few hundred thousand a year. The Red Sox decided to pay him $2.3 Million per year for I don't remember how many years. They may still be paying him. He rewarded them with a typical performance -- 3 wins and 11 losses and an era of about 5 over two years. The guy sucked before they signed him, they gave him a huge raise, and he sucked just as bad after they signed him. Just a horrible, horrible move.
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