Carlton Fisk
The bungling of Carlton Fisk’s contract is one of Boston’s greatest mistakes.
At the end of the 1980 season, Fisk became a free agent by accident. Sox GM Haywood Sullivan had put his contract in the mail one day after the deadline, accidentally rendering their star catcher a free agent.
In March 1981, the New Hampshire native signed a five-year deal with the White Sox. He and the team achieved a lot during his tenure. They won their first division title in 1983, he hit for the cycle in 1984, and won all three of his Silver Sluggers with Chicago.
But in June 1993, right after Fisk broke Bob Boone’s record for all-time games caught, the White Sox abruptly released him from the team while they were on a road trip. And when they made the postseason that fall, he went to the clubhouse to wish his former teammates good luck and was thrown out.
The horrible treatment and insult Fisk endured at the end of his time with the White Sox played a part in the catcher choosing to wear a Red Sox cap on his bronze Hall of Fame plaque, instead. Both teams retired Fisk’s number, and he’s in the Red Sox Hall of Fame as well as Cooperstown. Fenway’s left-field foul pole is named the Fisk Foul Pole in honor of his iconic “If it stays fair!” home run in the 1975 World Series.
But he should’ve switched Sox again before hanging it up.