People sometimes wonder how great Dawson might have been if it wasn't for his bad knees. He had 11 knee surgeries and two knee replacements. For years, he played in constant pain.
Dawson believed that getting away from the articifical turf in Montreal would prolong his career. He always had a desire to play for the Chicago Cubs. After the 1986 season, Dawson became a free agent and expressed his desire to play for the Cubs. Dallas Green, the Cubs' General Manager, did not wish to spend the money on Dawson--thinking that it was going to take a lot more than an expensive free agent signing to turn the Cubs around (the team had lost 91 games in 1986).
So, Dawson did something very unusual to make his wish to play for the Cubs come true. He handed the Cubs a blank contract--and asked the Cubs to fill in the amount! Eventually, the Cubs decided to pay Dawson $500k--an amount far below market value for the future Hall of Famer. Dawson went on to win a MVP with the Cubs--but the team still finished last that season.
Dawson declared that he loved the game so much that a major league team would have to "tear the uniform from his body" before he would quit. But, increasing pain from his knees forced him to reconsider while he was with the Boston Red Sox. Dawson said, "It's best that I walk away from the game while I can still walk myself."