Greatest Red Sox players who should have stayed in Boston

With all of the great players the Red Sox have produced over their long and storied history, here are the greatest who started their careers in Boston but didn’t get a chance to finish them there.

In the wake of the Red Sox trading Mookie Betts earlier this month, the team has taken a very public beating from large segments of the fanbase as well as the media at both the local and national level. While Betts’ departure is sure to be felt as the years go on, especially if he continues to produce at an MVP level, he’s not even close to being the only “what if?” in Red Sox history.

There have been several excellent homegrown players who seemed destined to spend their entire careers in a Red Sox uniform only to end up somewhere else. All these players have been among the best the team has produced, with two of them being enshrined in the Baseball Hall of Fame, one of them who should be in there if not for extenuating circumstances, and two others who were on track for Cooperstown-worthy careers before injuries derailed them.

The following players were all drafted and developed by the Red Sox and enjoyed success in Boston before leaving the team for various reasons and ending their careers elsewhere. These are my picks for the greatest players who should have been Red Sox for life. Let’s a look at them in chronological order from earliest to most recent.

(And before anyone asks me why Dwight Evans isn’t on this list, he played nineteen of his twenty seasons with the Red Sox and while we can lament that he didn’t finish his career with the team, they’d already gotten the very most from him before that final season in Baltimore).