Best Red Sox Players Of All Time: Top 5 Legendary Boston Athletes, According To Fans

Boston is a city known for its rich history, thriving downtown, delicious baked beans, and the amazing Fenway Park, which is home to the Boston Red Sox. Undoubtedly, there have been some historically great baseball players to come through Boston over the years, but who qualifies as the best Red Sox players of all time? 

Baseball fans are a passionate group willing to dedicate several hours of their days to watching baseball. However, according to a recent study, fans are also willing to travel, and spend big money, to watch their favorite sports teams play live. Whether it’s baseball, football, basketball, or another popular sport, American sports fans are a dedicated group. A survey of 2,000 self-identified sports fans found that the average sports fan is willing to travel nearly six hours and spend $762 just to see their favorite team play in person. Of course, not every fan can make the pilgrimage to Boston and Fenway Park just to watch the Red Sox play in person, and that’s okay, it’s still fun to watch the games on TV

Speaking of watching sports on TV and in person, another survey of American sports fans found that nearly two-thirds of sports fans are superstitious about watching their team play. A survey of 2,400 American sports fans found that the majority of them are superstitious about gameday to the point where 62 percent of them have blamed themselves for their favorite team losing a game. Much of this blame is superstitious in nature as respondents claim that behaviors such as wearing the wrong shirt or moving from their usual spot on the couch are to blame for their team’s loss. These superstitions also go beyond personal routines and behaviors as a whopping 38 percent of respondents claim that a family member is ‘bad luck’ to the point where 84 percent of those respondents have even asked that person to leave the room while the game is going on. That’s one way to keep the Red Sox in the pennant race. 

So, who are the greats that have run the bases at Fenway? StudyFinds did the research, consulting 10 sports and baseball-oriented websites in an effort to bring you the best Red Sox players ever. Our list comprises the five most frequently listed players from across these sites. As always, feel free to share your thoughts with us in the comments section below! 

Fenway Park
Fenway Park (Photo by Maxence Bouniort on Unsplash)

The List: Best Red Sox Players of All Time, According to Sports Experts

1. Ted Williams (1939-1942 & 1946-1960)

Topping the list of the best Red Sox players of all time is none other than the iconic and legendary Ted Williams. Of course, you’ll notice a gap in Ted Williams’ career because he enlisted in the military to help fight two wars – World War II and Korea. Still, Ted Williams is considered one of the best MLB players of all time as well as one of the game’s purest hitters

“Is there really any question here? A 19-time All-Star and a Red Sox lifer, Williams won two AL MVPs and finished in the top-10, 10 other times. He won six AL batting titles and four home run crowns. The scariest part about Ted Williams’ numbers is that he lost a full three seasons due to World War II and most of another two seasons due to the Korean War. ‘The Splendid Splinter’ was elected to the Hall of Fame in 1966 and his number, nine, was retired by the Red Sox in 1984,” explains Bleacher Report

Ted Williams ranks first in Red Sox history across several major statistical categories including batting average and slugging percentage. Williams is clearly considered one of the best hitters in the history of baseball, and a lot of experts will argue that he’s one of the best left fielders of all time as well. 

“Williams won six American League batting titles, including when he hit .406 in 1941, a single-season mark that seemingly won’t ever be approached again. ‘Teddy Ballgame’ also led the AL in on-base percentage in 12 different seasons, and his .482 career on-base percentage is best in MLB history. While there’s a debate to be had about whether Williams or Barry Bonds is the greatest left fielder of all time, it’s pretty clear that the 1966 Hall of Fame inductee is the best player to ever suit up for the Red Sox,” adds Audacy.  

It’s fun to speculate on how great Ted Williams’s career could have been had he not fought in two wars. As some experts will tell you, Williams’s statistics could have been untouchable by today’s standards.  “How long could Ted Williams have played if the DH was around in 1960? He batted .316/.451/.645 in that last season. If he didn’t have to worry about playing the field and could entirely focus on hitting, I imagine he’d have played longer than Julio Franco who retired when he was 48. If Williams could have done that and not have fought in two wars (WWII and Korea), how many hits could he have gotten? 4000? He basically missed five seasons because of the wars alone. It’s incredible to think that as great as Ted Williams’ career was, it could have been even greater,” writes Barstool Sports

2. Carl Yastrzemski (1961-1983)

Yastrzemski took over for Williams in left field after Williams retired from MLB, and Yastrzemski never looked back. With all of the pressure on him to follow in the footsteps of the great Ted Williams, Carl Yastrzemski stepped up and filled the gap left by Williams in 1960. 

“Yaz is perhaps best known for his 1967 season. He won the AL MVP behind a Triple Crown performance… The Red Sox won their first pennant in 21 years behind Yaz’s torrid hitting in the season’s final two weeks… Yaz had a prolific career. He was selected to 18 All-Star teams. He won three AL batting titles, finished top-10 for the AL MVP four times and won six Gold Gloves…. He is the only Red Sox in the 3,000-hit club. His number, eight, was retired by the Red Sox in 1989. Yaz was also elected to the Hall of Fame that year,” writes Bleacher Report

Between Yastrzemski and Williams, the Red Sox had two of the best left fielders of all time playing in Fenway Park for nearly 40 years straight. Yastrzemski carved out a name for himself rather quickly, too. Carl Yastrzemski won a Triple Crown by leading the American League in batting average, home runs, and RBIs, and he’s one of only two players to accomplish this feat over the last 50 years. 

“Sox fans were rather spoiled in that their team essentially went from one all-time great to another with no in-between time. Left-handed slugger Carl Yastrzemski debuted in 1961, and it didn’t take long for him to morph into one of the most dangerous hitters in the game. In the 23 years that followed, Yaz would win MVP and the Triple Crown, take home seven Gold Gloves and three batting titles, and participate in 18 all-star games. He’s Boston’s all-time leader in hits, runs, RBI, and doubles and was selected to the Hall of Fame in ’89,” explains Yardbarker

“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,” furthers The Champ Lair

3. Pedro Martinez (1998-2004)

Scowling his way into the third spot on the list is a true Boston fan favorite, Pedro Martinez. He was as fierce a competitor as the game has ever seen, and as a pitcher for the Red Sox for more than a decade, Pedro was an intimidating force on the mound for Boston. 

“Pedro ranks highest among the Boston pitching triumvirate because of when he pitched—in the heart of the Steroid Era, Pedro put together two of the finest full seasons of pitching in 1999 and 2000. A six-time All-Star in Boston, Martinez won two Cy Young awards and finished top-5 in another three. He also had two top-5 finishes in AL MVP voting, infamously finishing second for the award in 1999. A future Hall of Famer, Martinez has to be considered one of the most electrifying players ever to wear the Red Sox uniform. He’s also a Red Sox World Series champion,” writes Bleacher Report

For the record, Pedro Martinez was eventually inducted into the Hall of Fame in 2015. Pedro helped the Red Sox win the 2004 World Series, which was the team’s first MLB championship in nearly a century. In 1920, after winning three World Series, the Red Sox traded, or sold, Babe Ruth to the New York Yankees for $125K. This sparked the ‘Curse of the Bambino,’ and it plagued the Boston Red Sox franchise for decades after the sale. Boston suffered for over 80 long years without a World Series victory, but Pedro Martinez helped change that narrative and he became a Red Sox legend in the process. 

“All that Martínez would do in his seven seasons in Boston was put together one of the greatest peaks in MLB history, finishing in the top four in American League Cy Young voting on six occasions, winning the award in 1999 and 2000. Mind you, Martínez was putting together these all-time seasons at the same time that many hitters are believed to have been using performance-enhancing drugs. While others spent longer in Boston, Martínez was so dominant in his time there that his No. 45 was retired by the Red Sox in July of 2015, a month before he was inducted into the Hall of Fame with their hat on his plaque,” explains Audacy

Just say the name ‘Pedro’ in Boston and everyone knows exactly who you’re talking about. “Boston has had a lot of great players, pitchers, and personalities, but I think it’s fair to say they haven’t ever had another guy like Pedro Martinez. The righty had just won the ERA title in Montreal in ’97 when the Expos traded him to the Red Sox, and he instantly became a New England favorite. Over the next seven seasons, Martinez would win 117 games and post a 2.52 ERA in 201 starts. He won four more ERA titles in Boston, took home back-to-back Cy Young awards, made four all-star teams, and led the league in strikeouts three times. Pedro is one of just a handful of baseball royalty that is identifiable by just their first name,” furthers Yardbarker

4. Roger Clemens (1984-1996)

Roger Clemens, The Rocket, litters the top of Boston’s all-time pitching statistics and he brought home a lot of individual awards during his time in a Red Sox uniform. “The Rocket had a terrific 13-year run in Boston, distinguishing himself with three AL Cy Young Awards and six top-10 AL Cy Young seasons. A five-time All-Star, Clemens won the AL MVP in 1986 and finished third in voting in 1990. With Pedro Martinez’s greatness following immediately on the heels of Clemens’ infamous departure to Toronto, it can be easy to undervalue Clemens’ own contributions and brilliance in the Boston uniform,” writes Bleacher Report

Obviously, the days of players spending their entire career with one team are long gone, but Clemens was the face of Boston’s franchise for well over a decade. “The Rocket won the American League Cy Young Award in 1986, 1987 and 1991 as a member of the Red Sox, and also added the AL MVP in 1986. As a Red Sox, Clemens won the junior circuit’s ERA title on four occasions (1986, 1990, 1991 & 1992). Clemens also had two 20-strikeout games during his time with Boston, making him the only pitcher in MLB history to accomplish the feat multiple times. Connections to performance-enhancing drugs have kept Clemens out of the Hall of Fame to this point, but he’s unquestionably one of the greatest right-handed pitchers ever,” adds Audacy

Similar to some of the other all-time great baseball players of his era, Clemens has connections to steroids. However, unlike some of his contemporaries, Clemens was dominant from the start of his career, when steroids were not considered all that prevalent in baseball.

Regardless of the allegations, “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,” furthers The Champ Lair

5. David Ortiz (2003-2016)

The living legend, ‘Big Papi,’ David Ortiz was one of the best power hitters in MLB during his time in a Red Sox uniform. Ortiz is celebrated for helping Boston win three World Series championships in 2004, 2007, and especially 2013. 

David Ortiz 2008
David Ortiz (“David Ortiz 2008” by Keith Allison is licensed under CC BY-SA 2.0.)

“To fans of today’s generation, there is not a single player more identifiable with the Red Sox than David ‘Big Papi’ Ortiz. Ortiz arrived in Boston in ’03 after several lackluster campaigns as a Minnesota Twin and, simply put, developed into the most dangerous hitter in the American League. With the Red Sox, Ortiz made it to ten all-star teams, won seven Silver Slugger awards, and was a home run derby winner. But most importantly, he led Boston to three World Series championships and was the MVP of the 2013 Fall Classic. Ortiz is probably the greatest designated hitter in baseball history and was rightfully inducted into the Hall of Fame in 2022,” explains Yardbarker

Ortiz helped power the Red Sox back from a 3-0 series deficit in the 2004 American League Championship Series (ALCS) against the Yankees. His performance in that series is legendary, and Ortiz earned ALCS MVP honors for his efforts. It was the first time in history that a team came back when trailing three games to zero in the ALCS and it came against Boston’s bitter rival, the New York Yankees. The performance catapulted Ortiz into the conversation for one of the best Red Sox players of all time, to say the least. Still, Ortiz isn’t without his fair share of controversy. 

“It was leaked that Ortiz failed what was supposed to be an anonymous drug test in 2003 that was to determine if testing would be implemented in 2004. He claims it was an over the counter supplement and to his credit, he never failed a formal drug test despite being tested for over a decade after that. He has to make a list like this. You can make a case that he is the most important player in Red Sox history,” adds Barstool Sports

Again, ‘Big Papi’ is a legend in Boston and across the New England area. And as the experts explain, Ortiz was primarily used as a designated hitter (DH). Ortiz thrived in the DH role for the Boston Red Sox, and he made huge contributions to those three championship teams. David Ortiz also accumulated a plethora of individual awards and accolades to go with his three championships.

“Perhaps the most popular player in franchise history, Ortiz was a 10-time All-Star and seven-time Silver Slugger Award winner during his 14 years with the Red Sox. ‘Big Papi’ hit 483 of his 541 career home runs as a Red Sox, putting him second in franchise history in the category. Like his long-time teammate Ramírez, Ortiz was one of the greatest postseason hitters of all-time, as he homered 17 times in the postseason with the Red Sox. Ortiz was the ALCS MVP in 2004, the World Series MVP in 2013 and helped the Red Sox to win three World Series titles (2004, 2007 & 2013) during his decorated career. He was elected as a first-ballot Hall of Famer in 2022, and will go into Cooperstown with a Red Sox cap on his plaque,” furthers Audacy.

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