The first player on this list is the legendary Carlton Fisk, one of the greatest catchers in the history of the game and one of the biggest “should have spent his entire career in Boston” guys in Red Sox history. He was a local kid, born in Vermont and raised in New Hampshire, and after being drafted by the Red Sox in 1967, he made his debut in 1969 before sticking for good in the big leagues in 1971.
His list of achievements during his time in Boston between 1969 and 1980 are many. He was American League Rookie of the Year in 1972, also winning a Gold Glove that year. During his time as a Red Sox, he was a seven-time All Star who hit .284 with 161 home runs and 568 RBI. His totals would have been even higher but for the fact that he battled injuries in three of those seasons.
Fisk was a hard-nosed catcher who has some memorable moments in a Red Sox uniform, perhaps none more so than his dramatic walk-off home run in Game Six of the 1975 World Series. It’s one of the most iconic moments in baseball history and eventually led to the Red Sox naming the left field foul pole after him.
Fisk was a core member of those great Red Sox teams of the mid- to late-1970s that could never seem to quite get over the hump (or past the Yankees). He had a lot of memorable fights with Yankees players during that decade, especially with Lou Piniella and Thurman Munson. However, Fisk and several other Red Sox players were unhappy by the late 1970s with how little they thought they were being paid.
Then-Red Sox General Manager Haywood Sullivan held off on mailing Fisk a new contract after the 1980 season, missing the deadline and allowing Fisk to become a free agent. He signed with the Chicago White Sox and spent twelve seasons playing for them, continuing to put up fantastic numbers and cementing his eventual place in Cooperstown. When he retired he held the record for most home runs by a catcher (which was since broken by Mike Piazza) and most seasons played by a catcher (which still stands).
What makes Fisk’s departure hurt is that it was entirely self-inflicted by the Red Sox and their inept front office management. While Fisk ended up wearing a Red Sox hat on his Cooperstown plaque and had his number retired by the team, he’s always been No. 1 on my list of players who should’ve been on the team for his entire career.