MLB Top 5: Boston Red Sox Pitchers

This is the fifth and final article in a series that looks at the five best players at each position for the Boston Red Sox. In this installment, right- and left-handed starters, plus relief pitchers. 

The Red Sox outfielders might get a lot of credit for the team’s success, but Boston’s pitchers are no slouches. Included on these lists are a handful of Hall of Famers (including the all-time Major League leader in victories), along with one player who is having a little trouble with off-the-field issues and two top-notch closers.

The Best Pitchers in Boston Red Sox History

Right-Handed Starters

Honorable Mentions – Josh Beckett was a three-time All-Star during his seven seasons with Boston (2006-12). He reached double-digit wins five times, including a league-leading 20-7 mark in 2007, when he finished second in the Cy Young voting to CC Sabathia. Beckett was the MVP of the 2003 World Series with the Marlins and he added ALCS MVP honors to his resume with two wins against the Indians in 2007. He was 5-1 in eight postseason starts and went 89-58 in the regular season with 1,108 strikeouts (sixth-most in team history).

Bill Monbouquette was a four-time All-Star who went 96-91 in eight seasons with the Red Sox (1958-65). His best season was in 1963 when he set career highs with a 20-10 record, 174 strikeouts and 13 complete games. “Monbo” ranks seventh in franchise history in innings (1,622) and games started (228), and he sits tenth in strikeouts with 969.

Joe Dobson went 106-72 in nine seasons with the Red Sox, and he would have been better had he not missed two years of service in World War II. Dobson was an All-Star in 1948, but he had his best season the year before, going 18-8 with a 2.95 ERA. He ranks ninth in innings (1,544) and tenth in wins, games started (202), and tied for tenth with 17 shutouts.

The Red Sox have too many good righties, so sadly, Tim Wakefield lands just off the top five. The knuckleballer played 17 years in Boston (1995-2011) and was a part of two championship teams. Wakefield won 15 or more games three times, but his lone All-Star appearance came in 2009 when he went 11-5. In the postseason, he made 16 appearances, posting a 3-1 record against the Yankees and an 0-6 mark against everybody else. Wakefield is Boston’s all-time franchise leader in games started (430) and innings (3,006), and he ranks second in games pitched (590) and strikeouts (2,046) and third in wins (186-168).

5. Luis Tiant – He struggled in his first season after signing with Red Sox but bounced back to go 15-6 with a league-leading 1.91 earned run average in 1972. Over the next four years, he reached the 20-win mark three times and had two All-Star selections. “El Tiante” went 18-14 in 1975 and then added three more wins in the playoffs, but the Red Sox fell to the Reds in the World Series. Known for his unique delivery, Tiant fooled plenty of batters over his eight seasons in Boston. He sits fourth on the all-time franchise list in innings (1,774 2/3) and shutouts (26), fifth in wins (122-81) and games started (238), tied for sixth in complete games (113) and seventh in strikeouts (1,075).

4. Smoky” Joe Wood – Nicknamed for his blazing fastball, Wood used two fantastic seasons to make his legacy. After three average seasons to start his career, he found success in 1911, winning 23 games and striking out 231 batters. The following year, Wood was even better, winning 16 straight games en route to a 34-5 mark (a single-season team record for victories) with 258 strikeouts and league-leading totals in wins and shutouts (10, which is tied for the team record).

In the 1912 World Series, he went 3-1 to help the Red Sox beat the Giants. In July 1913, Wood slipped and broke his right thumb while fielding a ground ball and was not as dominant after he returned, although he went 15-5 with a league-best 1.49 ERA in 1915. Wood holds the all-time team record with a 1.99 career ERA, and he ranks third in shutouts (28), fourth in complete games (121), sixth in wins (117-56) and ninth in strikeouts (986).

3. Pedro Martinez – Every team has that one move that changes the course of history. For the Red Sox, that could very well be a late 1997 trade with the Expos. Martinez was the key piece, coming off a 17-8 record and a Cy Young award. He went right to work, winning at least 16 games in five of his seven seasons with Boston. After finishing second in the 1998 Cy Young voting (to Roger Clemens, more on him in a minute) with a 19-7 record and 251 strikeouts, he won the next two.

Martinez won pitching’s Triple Crown in 1999, going 23-4 with a 2.07 ERA and a team-record 313 strikeouts. He nearly repeated the feat the following year, leading the league with a 1.74 ERA and 284 strikeouts while posting an 18-6 record and winning the Cy Young award unanimously. Martinez went 6-2 in 13 postseason appearances and won a game in the 2004 World Series to help the Red Sox win their first title in 86 years. He went to four All-Star Games and was the MVP of the 1999 contest. Martinez ranks third in franchise history in strikeouts (1,683), tied for sixth in wins (117-37), and tenth in earned run average (2.52). He was inducted into the Baseball Hall of Fame in 2015.

2. Cy Young – Denton True Young earned his nickname due to his fastball resembling the speed and damage of a cyclone. He spent 11 seasons in the National League before the turn of the 20th century, amassing 286 victories with the Cardinals and Cleveland Spiders. Young joined the Americans in 1901 and immediately showed the upstart American League how dominant he was by winning the pitching Triple Crown with a 33-10 record, a 1.62 earned run average and 158 strikeouts.

Young went 93-30 in his first three seasons in Boston and added two more victories in the 1903 World Series. He won 26 games with a 1.97 ERA for the pennant-winners in 1904 but did not get to pitch in the World Series because the Giants refused to recognize the “junior” league. Young threw two no-hitters with Boston, including the American League’s first perfect game in 1904.

With Boston, Young is tied at the top of the leaderboard in wins (192-112) and shutouts (38, including 10 in 1904 which is tied for the best single-season mark in team history), and he holds the top spot by himself in complete games (275, which includes 30 or more in a season five times and a team-record 41 in 1902). He also ranks second in ERA (2.00, including a 1.26 mark in 1908), third in games started (297) and innings (2,728 1/3, including a team-record 384 2/3 in 1902), and fifth in strikeouts (1,341).

Young retired after the 1911 season with Major League records in wins (511), losses (315), games started (815), complete games (749), and innings pitched (7,356), none of which will probably ever be approached. He was inducted into the Baseball Hall of Fame in 1937 and passed away in 1955. Major League Baseball named the award for best pitcher after him the following year.

1. Roger Clemens – How do you top the guy who had the best pitcher award named after him? You find someone who won it seven times, including four with the Red Sox. Clemens had two decent seasons before breaking out with an incredible 1986 campaign that saw him win both the MVP and Cy Young awards after posting league bests with a 24-4 record and a 2.48 ERA along with 238 strikeouts (including a record 20 in a game). He made five starts in the postseason, helping the Red Sox reach the World Series before falling to the Mets.

The following year, Clemens won the Cy Young award again after leading the league in wins (20-9), complete games (18), and shutouts (7) to go along with 256 strikeouts. He led the league in complete games and shutouts once again in 1988 and also posted an American League-high 291 strikeouts. From 1986-92, Clemens made five All-Star teams and won at least 17 games in all seven seasons. He won his third Cy Young award in 1991 with an 18-10 record and a league-best 241 strikeouts.

Clemens finished his Red Sox tenure tied with Young for first on the all-time list in wins (192-111) and shutouts (38) and in first by himself with 2,590 strikeouts. He sits second in games started (382) and innings (2,776) and ninth in complete games (100). After four down seasons from 1993-96, Clemens left Boston. He went on to win two Cy Young awards with the Blue Jays (1997-98) and one each with the Yankees (2001) and Astros (2004). However, despite all the accolades, Clemens may never get into the Hall of Fame due to his temper and his ties to performance-enhancing drugs.

Left-Handed Starters

Honorable Mentions – Bill Lee went 94-68 in 10 seasons with the Red Sox, and he won 17 games in three straight years (1973-75). The best of these seasons was the first, when he earned his only All-Star selection after going 17-11 with a 2.95 earned run average and a career-high 120 strikeouts. Nicknamed “Spaceman” for his antics and crazy quotes, Lee made two starts in the 1975 World Series but did not get a decision.

Bruce Hurst had an 88-73 record in nine seasons with Boston (1980-88). He won two games against the Mets during the 1986 World Series and was an All-Star the following season when he went 15-13 with a career-high 190 strikeouts. However, Hurst’s best season with the Red Sox was arguably 1988, when he went 18-6 and fanned 166 batters. He ranks eighth in team history in strikeouts (1,043) and is tied for eighth in games started (217).

When Chris Sale has been on the mound for the Red Sox, he has had moments where he is dominant. However, he has spent more time off the field than in the past four seasons. Sale’s first season in Boston was in 2018 when he finished second in the Cy Young voting after going 17-8 with a 2.90 ERA and a league-leading 308 strikeouts (a total that is the second-best in a single season in franchise history). The following year, he went 12-4 with a 2.11 ERA and 237 strikeouts and was a part of Boston’s championship team. Sale dropped to 6-11 in 2019 and has had a litany of injuries since. He currently has a 45-27 record in six seasons with Boston.

5. Jon Lester – He was a three-time All-Star who won 15 or more games five times during his nine-year Boston tenure (2006-14). Lester’s best season was 2010 when he went 19-9 with a 3.25 ERA and 225 strikeouts. He went 3-0 in Boston’s two World Series victories (2007 and 2013) and had a 6-4 record in 13 postseason games with the Red Sox. Lester ranks fourth in team history in both strikeouts (1,386) and games started (241), and he is ninth in wins (110-63). The Red Sox traded Lester away during the 2014 season and after stints with four other teams, he retired before the 2022 season.

4. Babe Ruth – With the popularity of Shohei Ohtani, many people are looking at Ruth’s career as a comparison. Before he was the “Sultan of Swat,” George Herman Ruth was a top-notch pitcher, going 89-46 in six seasons with the Red Sox. From 1915-17, Ruth went 65-33 and led the league with a 1.75 ERA in 1916. Ruth ranks fifth on the franchise list in ERA (2.19), eighth in complete games (105) and tied for tenth in shutouts (17). He went 3-0 during Boston’s run of three championships in four years before converting to full-time outfielder.

Ruth led the league with 11 home runs in 1918 then shattered the single-season mark with 29 homers along with 113 RBIs the following year. Ruth had so much potential as a batter that owner Harry Frazee sold him to the Yankees to help get out of debt from his theater. After the move, the Red Sox didn’t win another title until 2004.

3. Dutch Leonard – A teammate of Ruth’s on two Boston championship teams, Hubert “Dutch” Leonard went 90-64 in six seasons with the Red Sox (1913-18). His best season was 1914 when he went 19-5 with 176 strikeouts and an otherworldly 0.96 ERA, a mark that set team and league records. Leonard reached the 15-win mark in four straight seasons, and he ranks fourth on the franchise list in ERA (2,13) and fifth in shutouts (25).

2. Lefty Grove – He began his career with the Athletics and won 195 games in nine seasons before Philadelphia traded him to Boston in 1933. Although he never matched his success with the A’s (he led the league in strikeouts seven times, ERA five times and wins four times), Robert “Lefty” Grove was still able to compete. After a down year in his first season with the Red Sox, Grove rattled off five straight All-Star seasons. During that stretch, he went 20-12 in 1935 and led the league in strikeouts and ERA four times apiece.

Grove did all this despite losing his fastball (the pitch that brought him success in Philadelphia), which allowed him to develop the “curve and control” he was known for in Boston. Despite losing effectiveness as he aged, Grove held on for two more years in Boston, gaining his 300th win on July 25, 1941. Lefty finished 105-62 with a 3.34 ERA and 743 strikeouts in his Boston career. He ranks fifth on the franchise list in complete games (119) and tenth in innings (1,539 2/3). Grove was inducted into the Baseball Hall of Fame in 1947.

1. Mel Parnell – He used a plus curveball and slider to win 15 or more games five times in a six-year span (1948-53). Parnell earned his first All-Star selection in 1949 when he led the league with a 25-7 record, a 2.77 earned run average, and 27 complete games. He won 18 games each of the next two seasons, including an 18-11 mark in 1951 that got him his second and final All-Star honor. In 1953, he went 21-8 with a career-high 136 strikeouts.

However, the following year, Parnell was hit by a pitch that broke the ulna bone in his arm. Although he was never the same pitcher again, he had one final big moment when he pitched a no-hitter against the White Sox on July 14, 1956. He retired at the end of the season and ranks fourth in wins (123-75), fifth in innings (1,752 2/3), sixth in games started (232) and shutouts (20 and tied for sixth in complete games (113).

Relief Pitchers

Honorable Mentions – Jeff Reardon did not pitch even three full seasons with the Red Sox, but he went 8-9 with a 3.41 earned run average and 88 saves, including 40 in his All-Star 1991 season.

Derek Lowe converted to a starter midway through his 17-year career, but before that, he was a reliever with Boston, amassing 85 saves, with a career-best and league-leading 42 in his All-Star season in 2000. Lowe earned his other All-Star selection as a starter two years later when he went 21-8 with a 2.58 ERA. He went 70-55 overall in eight seasons with the Red Sox.

Tom Gordon went the opposite of Lowe, beginning his career as a starter and converting to a closer with Boston. After two seasons as a starter, “Flash” was brilliant at the back end of the bullpen, posting a team-record 46 saves to earn an All-Star selection and win the Rolaids Relief Award in 1998. Gordon missed the 2000 season after undergoing Tommy John surgery and he signed with the Cubs in 2001. He finished his four-year Red Sox tenure with a 25-25 record and 68 saves.

5. Ellis Kinder – He was around at a time before there were specialized bullpen roles. Kinder began his career as a starter (he went 23-6 in 1949) and long reliever before moving to the back of the bullpen in the early 1950s. He led the league in saves with 16 in 1951 and topped the American League again two years later with a career-high 27. Kinder went 86-52 with a 3.28 ERA and 93 saves in 365 games (eighth-most in team history) over eight seasons (1948-55).

4. Dick Radatz – He was the first true closer in team history, and he earned two All-Star selections during his five-year run in Boston (1962-66). Radatz had four straight seasons with 120 innings, 120 strikeouts, and 20 saves, and he led the league in saves twice. Nicknamed “the Monster,” Radatz finished his Red Sox tenure with a 49-34 record, a 2.65 ERA, 627 strikeouts in 557 1/3 innings, and 102 saves, which ranks fourth in team history. He was traded to Cleveland in 1966 and bounced around a bit before ending his career with the expansion Expos in 1969.

3. Bob Stanley – No matter what role the Red Sox needed him to play, he was ready. Stanley was a starter 80 times during his 13-year career, and he also excelled as a long reliever (he ranks sixth on the franchise list with 1,707 innings), a middle reliever (377 games finished), and a closer (his 132 saves rank second in team history). Stanley went 15-2 as a long reliever in 1978 and had his first All-Star selection after posting a 16-12 mark as a starter the following year. Throughout the 1980s, he spent most of his time as a short reliever, and he made his only other All-Star team after saving a career-high 33 games in 1983.

Although Stanley is Boston’s all-time leader in games pitched (637) and ranks eighth in wins (115-97), he is best remembered for throwing a wild pitch that brought home the tying run in Game 6 of the 1986 World Series against the Mets. On the next pitch, Mookie Wilson hit the ground ball that went through the legs of Bill Buckner, allowing New York to improbably win the game and finish off the series victory the next night.

2. Craig Kimbrel – We already looked at his time in Atlanta, and while he wasn’t quite so dominant for quite so long in Boston, Kimbrel was still a top-notch closer. He was an All-Star in all three of his seasons with the Red Sox, but his 2017 season was the best (although not strictly in terms of saves). That year, Kimbrel went 5-0 with an Atlanta-like 1.43 earned run average and 126 strikeouts in just 69 innings (an incredible 16.4 K/9 rate). In 2018, he “dropped” to a 2.74 ERA and 96 strikeouts, but had 42 saves, which is tied with Lowe for second-most in team history.

Overall, Kimbrel went 12-7 with a 2.44 ERA, 305 strikeouts in 184 1/3 innings, and 108 saves. He added six more saves in the playoffs and had one in Boston’s 2018 World Series victory. Kimbrel signed with the Cubs the following year.

1. Jonathan Papelbon – He was a four-time All-Star who topped the 30-save mark in six of his seven seasons with Boston (2005-11). He went 4-2 with a nearly unhittable 0.92 ERA and 35 saves to finish second in the Rookie of the Year voting to Justin Verlander in 2006. Papelbon was just as dominant in the playoffs, going 2-1 with seven saves and a 1.00 ERA in 18 postseason games, including three saves during Boston’s 2007 World Series win.

Overall, he went 23-19 with a 2.33 ERA and a team-record 219 saves, and he also ranks fourth in franchise history with 396 games pitched. Papelbon signed with the Phillies in 2011 and continued to be one of baseball’s best closers for the next four years. He was sent to the Nationals during the 2016 season and was released the following year after a declining performance and an intercostal (rib muscle) strain.

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Previous Series

A look back at the Boston Red Sox

Boston Red Sox Catchers and Managers
Boston Red Sox First and Third Basemen
Boston Red Sox Second Basemen and Shortstops
Boston Red Sox Outfielders and Designated Hitters

A look back at the Baltimore Orioles

Baltimore Orioles Catchers and Managers
Baltimore Orioles First and Third Basemen
Baltimore Orioles Second Basemen and Shortstops
Baltimore Orioles Outfielders and Designated Hitters
Baltimore Orioles Pitchers

A look back at the Atlanta Braves

Catchers and Managers
First and Third Basemen
Second Basemen and Shortstops

A look back at the Arizona Diamondbacks

Catchers and Managers
First and Third Basemen
Second Basemen and Shortstops

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