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).

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.

The next guy on the list was a teammate of Carlton Fisk’s and one of the greatest phenoms the Red Sox have ever drafted and developed. Fred Lynn made his major league debut partway through the 1974 season before coming up for good as a rookie in 1975 and he announced his arrival in a big way. Lynn hit .331 with 21 home runs and 105 RBI in 1975, becoming the first and to date only player to win his league’s Rookie of the Year and MVP awards in the same season.

Lynn continued to hit at a torrid pace in his seven seasons in Boston, compiling a .308 average with 124 home runs and 521 RBI. Lynn was also a wizard in center field, winning four Gold Gloves during his Red Sox career to go along with a batting title in 1979 when he led the American League with a .333 average. Lynn was, along with teammate Jim Rice, one of the Gold Dust Twins as the pair of highly touted rookies were called.

Along with Dwight Evans, they made up one of the greatest outfields in Red Sox history, only being challenged for that distinction by the Mookie Betts/Jackie Bradley/Andrew Benintendi triumvirate of 2017-2019. Lynn was fearless in the field, diving and crashing into the wall to get to every ball he could. Unfortunately, that took a toll on his body as he started to suffer from knee injuries by 1980.

The Red Sox inexplicably traded Lynn to the California Angels before the start of the 1981 season and while he continued to enjoy some success over the remainder of his career, he never again hit the heights he did in Boston as the injuries limited him to the day he retired. Lynn is one of the biggest “what could have been” stories in Red Sox history, not only in terms of ending his career in a different uniform, but also regarding the heights he could have reached had he stayed healthy.

This one is probably going to be the most polarizing on the list because with Roger Clemens, you either love him or you hate him. Growing up in the 1980s and early 1990s, he was my favorite pitcher and one of my favorite Red Sox players. We all know about the PED accusations that have followed him around since the end of his career, so for the sake of this article let’s look solely at what he did in a Red Sox uniform.

Clemens spent twelve seasons pitching for the Red Sox and during that time was the premiere power pitcher of his era. In his Red Sox career, he won 192 games (a franchise record) with 2,590 strikeouts (also a franchise record) and an ERA of 3.17. He won both the American League Cy Young and MVP awards in 1986 and has a list of accomplishments in Boston too long to list here (plus, I already covered them in a previous article on his Hall of Fame candidacy).

Clemens was coming off a relatively poor stretch in his last four seasons in Boston, only going 40-39, when he became a free agent after the 1996 season. Then-General Manager Dan Duquette offered Clemens the largest contract to that point in the history of the Red Sox and said, in a widely misquoted statement, that the team “hoped to keep him in Boston in the twilight of his career.” Citing a wish to pitch closer to his Texas home, Clemens ended up signing with…the Toronto Blue Jays?

After Toronto, Clemens went on to pitch for the New York Yankees and Houston Astros and, upon winning two World Series with the Yankees, became a villain to Red Sox Nation. Fans have softened a bit on Clemens in his retirement, but he’s still a polarizing figure. What can’t be denied is that even after leaving in 1996, he was one of the greatest pitchers in franchise history (and in league history when the totality of his career is taken into account). It’s a shame he wasn’t able to do all of what he did in a Red Sox uniform (and without the taint of PEDs).

Another favorite of mine growing up, Wade Boggs was the Red Sox third basemen for the majority of the 1980s into the early 1990s. He spent eleven seasons with the Sox and was one of the greatest hitters of the decade, hitting over .300 for the first ten seasons of his career before dipping to .259 in 1992, his last with the Red Sox.

Boggs won six Silver Slugger awards and five American League batting titles as a member of the Red Sox and holds the career record for batting average at Fenway Park with a .369 mark. In his Red Sox career, he hit .337, albeit with only 85 home runs and 690 RBI. He had seven consecutive seasons of 200 or more hits, a record that stood until it was broken by Ichiro Suzuki decades later.

Boggs was a free agent after the 1992 season and signed with the hated New York Yankees, with whom he played for five seasons (and won a World Series in 1996) before finishing his career with two seasons playing for the expansion Tampa Bay (Devil) Rays. Boggs ended up collecting his 3,000th hit in a Devil Rays uniform to go along with his career .328 average, marks that helped him easily get into Cooperstown.

While his number was retired by the Red Sox and he wears a Red Sox cap on his Hall of Fame plaque, it’s always been a shame that Boggs wasn’t able to continue his exquisite hitting and fielding (he won two Gold Gloves after leaving the Red Sox) in Boston and spend his entire career with the team.

You knew he had to be on this list, right? I’m not trying to beat a dead horse…Mookie Betts is a Dodger now, the trade is done, and it’s time for us to all move on. And perhaps it’s recency bias, but I think it’s safe to say that when he career finished, Red Sox fans will still look back at Mookie Betts and wonder how and why he didn’t spend his entire career in Boston.

In just six full seasons with the Red Sox, Betts hit .301 with 139 home runs and 470 RBI. He won four consecutive Gold Gloves, three Silver Sluggers, an American League MVP award, an American League batting title, and a World Series. A true five-tool player, his dazzling combination of speed, power, and grace, especially for a player of his relatively small stature, made him the most complete player the Red Sox had developed since Carl Yastrzemski.

Betts also looks to be well on his way to Cooperstown if he can continue this pace of production for another ~5-7 years. And of course, now he’s gone. I’m not going to belabor the point as I’m sure by now every Red Sox fan understands why the team felt they had to trade away the face of their franchise. Whether or not they agree with those reasons is still up for debate and probably will be for many, many years.

One thing I think we can all agree on, though, is that if the Red Sox had planned better four or five years ago, Mookie would have been a Red Sox for life instead of only six years.