Top 25 Greatest Players in Boston Red Sox History

Table of Contents

The Boston Red Sox.

One of the most iconic franchises across the sporting globe, the mere mention of the 21st century’s most successful World Series team will have fans of all generations conjuring up images of the glory days.

Whether it’s the ‘Impossible Dream’ as autumnal shades grew from the Summer of Love in 1967 or that Carlton Fisk home run in 1975 to break the Cincinnati Reds, the Red Sox have provided some of America’s most heart-stopping sporting moments.

Still, as we close in on a half-decade without the Crimson Hose sitting atop the baseballing ladder, now seems like an apt time to reflect on some of the best players in their long, illustrious history.

Thousands have donned one of the most instantly recognizable uniforms on Planet Earth, so, as you can imagine, it’s far from an easy task to whittle down any all-time list, no matter the size.

However, these guys are worthy of a mention.

Indeed, they hold a special place in the hearts of many. The Red Sox Nation owes so much to these few exalted individuals; it only seems fair to compile a list celebrating their incredible greatness.

After all, these are the ones who’ve reached the top—the ones who inspire youngsters to pick up a bat and dare to dream.

Writing about them is as much joy as it was watching them; I can tell you that much. Let’s relive the moments together and spend some time thinking about the inductees to this mini-Hall of Fame.

They deserve that much!

So, grab a coffee (or a Sam Adams if you really want to have a good time), and let’s countdown the top 25 greatest players in Boston Red Sox history.

25. Tim Wakefield

Ranking sixth in the WAR standings for the Red Sox is no mean feat, and Tim Wakefield’s 17-year stretch with that trademark knuckleball style is one of the most impressive feats of endurance in modern baseball history.

25. Tim Wakefield

I know what you’re thinking, Mo Vaughn’s name was infamously included in the Mitchell Report back in 2007 as Senator George Mitchell exposed the use of performance-enhancing drugs rife in the sport.

Of course, that is worthy of discussion, but – the fact is – the 1995 American League MVP was a freak of nature even before the distasteful events later in his career.

With the Red Sox, the fact he’s fifth in the OPS rankings should not be forgotten.

23. Rico Petrocelli

A stalwart at shortstop, Rico Petrocelli has been part of two of the Red Sox’s most memorable nights in history, winning the World Series in both 1967 and 1975.

Modern statistical metrics would probably give the Brooklyn-native a much higher ranking here, but, as a lifelong and loyal servant, this 1997 Hall of Fame inductee will go down fondly in the baseballing annals.

22. Reggie Smith

Probably more famous for his time with the Cardinals and the Dodgers, let’s try not to forget what an impact Reggie Smith made during his early days with the Red Sox.

Making two All-Star games between 1966 and 1973, he twice led the American League for doubles while based in Boston, a feat he never managed after he’d move back west.

21. Manny Ramirez

While we’d love to sit back and remember Manny Ramirez’s partnership with David Ortiz, taking the Dominican native’s career in its own right is the least an all-time great deserves. 

Every single season he played with the Red Sox saw him included in the All-Star team, and only two occasions saw him miss out on a coveted Silver Slugger. 

The 2004 World Series MVP, not even a relatively sour end to his time with the franchise, can tarnish his legacy. 

20. Dom Dimaggio

The fact Dom Dimaggio is on this list shows just how good he was.

Even though players such as Bobby Doerr, Johnny Pesky, and Ted Williams stole most of the limelight during the famed 1940s era, the obvious problems being THAT guy’s brother brings in comparison, the younger of the Dimaggio clan earned his place in history.

A seven-time All-Star, his career average of 2.98 chances per game is a record amongst American League outfielders.

19. Luis Tiant

One of the most inspiring stories on this list, Tiant’s rise to the Red Sox Hall of Fame, didn’t start until he was brought into the big leagues at the age of 30.

A pillar of their pitching in the 1970s, this two-time All-Star threw two complete games (including a shutout) in the World Series, famously getting a no-decision in the much-talked-about Game 6.

A big-play guy.

18. Jimmie Fox

During the 1938 season, Jimmie Fox hit 50 home runs and batted at .349.

Throw in the fact he won a third MVP award and set an American League record by walking six times, and you start to get a feeling for how talented one of the sport’s early stars really was.

We can only imagine how high up he’d be if this slugger had played for the Red Sox longer.

17. David Ortiz

To be as dominant a figure as David Ortiz and get away with it takes a certain level of talent. Sadly, most of us who walk the earth will simply never have that.

Luckily, ‘Big Papi’ did. And does, really.

His iconic 34 jersey has been retired as a mark of respect from the Red Sox nation to a seven-time All-Star who hit 483 home runs and boasted a .956 OPS during his successful spell between 2003 and 2016.

16. Lefty Grove

Lefty Grove definitely has a case to be considered one of the greatest pitchers in baseball history.

Times may have moved on from Lefty’s heyday between 1925 and 1941 (joining the Red Sox in 1935), but the Maryland-native will be a celebrated name for as long as the game is played.

5th in CG and 10th in IP, Grove was an All-Star in five out of eight seasons with the franchise.

15. Carlton Fisk

‘The Commander’ (as he became known) was the first man ever to be voted the American League Rookie of the Year in a unanimous decision back in 1972.

While that’d have been a career highlight for many, FIsk’s iconic home run in the 1975 World Series changed how baseball was broadcast forever. Just watch it below. We know you’ve seen it a thousand times or more but, come on, isn’t it amazing?

14. Jason Varitek

No one has ever caught more no-hitters in the history of Major League Baseball than Jason Varitek.

You might hear that often for two reasons. One, it’s absolutely mind-blowing. Two, it’s otherwise difficult to measure just how important he was to the World Series victories of 2004 and 2007.

A leader in every sense of the word, the three-time All-Star ranks first in games caught (1,546) in franchise history.

13. Bobby Doerr

A Red Sox lifer, Bobby Doerr batted .300 three times between 1937 and 1951 (losing out on a year due to military service) and drove more than 100 runs on six different occasions.

Another to have his jersey number retired (1) Doerr made nine All-Star teams as a major factor in the legendary Teammates faction we mentioned earlier.

A bridge between the pre-war baseball era and beyond, Doerr is an all-time great.

12. Dustin Pedroia

A four-time Golden Glove winner and a hitter with the kind of power one may not expect, he remains the last of the 2007 World Series team to be at the club.

One of few men to have followed up winning Rookie of the Year with an MVP award the season after, Pedroia’s peak period will be remembered even more fondly when he does finally leave Fenway Park.

11. Nomar Garciaparra

It’s hard to argue that anyone set the league on fire from their debut as much as Nomar Garciaparra did back in 1997.

The All-Star shortstop set the record for a rookie making their way in the major leagues, batting at a .306 average across a 30-game hitting streak to go alongside his 30 home runs.

Things may have slowed down towards the end, but his 2004 departure saw him leave with 178 home runs and a .323 average across nine seasons for the Red Sox.

Got to be one for the Hall of Fame in the future.

10. Joe Wood

Ok, the chances of anyone on this planet being alive when ‘Smokey Joe’ Wood was pitching for the Red Sox are about as remote as it gets.

Still, the legend is what our grandfathers’ grandfathers would have told future generations about, and, hey, what are we if not romantics?

The 1912 World Series saw the then 22-year-old pitcher become the first pitcher to hit over nine strikeouts in a competition game as he battled Walter Johnson and came out on top.

9. Jim Rice

Finally, a bonafide Hall of Famer, Jim Rice’s 16-year career with the Red Sox was full of the sort of highs many of us mere mortals can only dream about.

Making eight All-Star teams, the team captain from 1985 until his retirement is still the only player to sit top of the HR, RBI, and triples rankings in the same year.

21 assists as a left-fielder across the 1983 season were the most anyone had managed in just under forty years, and he finished with 137 to his name overall.

The number 14 jersey was retired in his honor, and, looking at those numbers, you have to say it was the right decision.

8. Wade Boggs

One of the elite contact hitters of all time, Wade Boggs, will need little introduction to the Red Sox Nation.

Still, who gets tired of talking about how great the mustached master was?

Ranking second in AVG and 3rd in OBP in Red Sox history, Boggs was an eight-time All-Star and recorded 2.1 innings of pitching at Major League level.

So good, even a move to the Yankees doesn’t matter. Well, too much, anyway.

7. Dwight Evans

During an almost two-decade career in Boston, Dwight Evans batted at a .272 average, recording 379 home runs, and won eight Golden Gloves to go alongside his two Silver Sluggers.

Quite the crowded mantlepiece then.

His frankly underrated batting skills see him boast a 66.5 WAR, amongst the best in history.

6. Tris Speaker

A two-time World Series champion between 1907 and 1915, the efforts of Tris Speaker helped build the platform for the Red Sox to build on going forward.

Before the advent of home run fencing, the powerful hitter would regularly hit doubles and more, winning MVP in 1912 with an OBP of 4.64.

Granted, we’re talking about a different era for the sport, but those are some ridiculous numbers.

5. Cy Young

The first man to ever pitch a perfect American League game, Cy Young is another who cannot be ignored simply because he played well over 100 years ago.

We owe him that much.

Despite joining the Red Sox at the ripe old age of 34, the Ohio-native is tied first in all-time shutouts (38), he boasted a 2.00 ERA while in the final stages of his career in Boston.

In many ways, it was a more challenging game then, given the lack of quality equipment and modern-day training methods.

With that in mind, he deserves the utmost respect.

4. Pedro Martinez

It’s hard to think of a more thrilling player in Red Sox history.

One of the greatest power pitchers in baseball history, his 1999 and 2000 seasons are arguably the greatest in Major League history.

Seven shutout innings in the 1999 AL Championship Series gave the Yankees their only loss of that postseason, while the turn of the millennium saw him post a mind-bendingly good 1.174 ERA.

An electrifying personality, it’s just a shame his career in Beantown wasn’t longer.

3. Roger Clemens

‘Rocket’ boasts an all-time record SEVEN Cy Young awards and matched that very man with 38 shutouts between 1984 and 1996.

Using WAR, Clemens is the greatest pitcher in Red Sox history with a daunting record of 81.0.

Yes, you read that right. Eighty-one.

The move to the Yankees shouldn’t sour everything Clemens did at Fenway Park. A five-time All-Star, no one will wear the number 21 jersey as a result of his performances.

Given those numbers, it’s hard to blame them!

2. Carl Yastrzemski

A 23-year career with the Red Sox, Carl Yastrzemski can indeed consider himself the greatest Red Sox player currently walking the face of God’s green earth.

The franchise’s leader in RBIs, hits, runs, and games played (amongst others) literally the only disappointment in his career is that we never saw him line-up alongside Clemens.

An 18-time All-Star and the Red Sox player in the 3,000-hit club, he set a record in 1967 that has never been broken.

Indeed, he won the AL MVP alongside a Triple Crown performance. It still boggles the mind today.

1. Ted Williams

Can you imagine a world in which ‘The Splendid Sprinter’ didn’t lose three years of his career due to military service?

The greatest hitter in franchise history, Ted Williams was a nineteen-time All-Star, a six-time batting champion in the AL, and a two-time Triple Crown winner.

First in AVG, OBP, SLG, OPS, HR, and BB, not even those statistics can do his greatness justice.

From the Red Sox Nation: thank you, Ted.

Michael Specter
Michael Specter
Mike holds a Degree in Sports Coaching from the University of Minnesota and has held managerial and baseball head coaching roles at the college level.