The Boston Red Sox have been out of playoff contention these past couple of seasons. Their front office has recently worked to address pressing needs, signing and adding proven, capable starting pitchers with All-Star potential. The additions of Garrett Crochet, Walker Bueler, and Patrick Sandoval to a promising and capable rotation from 2024 will significantly improve the team’s overall outlook heading into spring training.
Add to this the signing of Aroldis Chapman at the back end of the bullpen, and Red Sox fans should feel relatively secure during high-leverage situations in the later innings. The lineup continues to boast young sluggers Jaren Durran and Tristan Casas, who are still short of the 6-year service requirement for possible free agency. Boston has a very talented core of players to build a contender. Now that any concerns with the starting rotation have been addressed, fans will have plenty to be excited about in 2025 and beyond.
The Red Sox have had strong rotations at various times over the years. This raises the question and fun debate of who are, or were, the best Boston Red Sox pitchers over their proud history in America’s greatest sports town. Here is a subjective list with some omissions, especially from the Dead Ball era. Let the debate begin.
“El Tiante” was a Cuban ace for the Red Sox during their successful 1975 run when they came within one game of taking down the Big Red Machine in the World Series. The heartbreaking loss was hardly Tiant’s fault as he was a perfect 3-0 for that postseason.
That included a dazzling complete-game shutout at Fenway over a Reds lineup that was stacked with future Hall of Famers. Overall, Tiant had 26 complete game shutouts as a Red Sox pitcher, a testament to his frequent dominance. Tiant brought a style to the mound that was unorthodox, deceptive, and highly effective.
The fireballing lefthander’s tenure in Boston was frustrating towards the end, but his 2017 season will rank quite simply as the greatest of any Red Sox lefthander. His 308 strikeouts and 214 innings pitched topped all American League pitchers that year. The following season, however, won the hearts of Fenway faithful.
“The Conductor” showed dominance in the playoffs and also came out of the bullpen at times to hold the lead. Sale showed stamina and versatility as Boston’s ace during the 2018 World Series.
Perhaps his greatest moment with the Red Sox was coming out of the ‘pen in game five and striking out Manny Machado (then of the Dodgers). That would seal the deal, get the save and final out, and win it all once again for Boston.
200 wins is a modern gold standard for success and longevity as a starting pitcher. The late Tim Wakefield achieved precisely that while wearing a Red Sox uniform. Wakefield personified grit, durability, and toughness over 17 years as a starting pitcher in Boston.
The Pirates initially drafted Wakefield as a power-hitting first baseman but reinvented himself as a crafty knuckleballer who could throw strikes. A 2016 inductee into the Boston Red Sox Hall of Fame, Wakefield remains the team’s all-time leader in innings and starts.
He was a two-time World Series champion with the club, helping the Red Sox postseason efforts as a starter and in high-leverage relief roles.
When the Red Sox acquired Martinez in 1998, he was just months removed from being declared the 1997 National League Cy Young Award winner. He had delivered a historic season of total dominance with the Montreal Expos in ‘97, and experts were left wondering how he could possibly duplicate that performance.
Upon arrival in Boston, Pedro’s stock kept climbing and climbing, with individual statistics, records, and accolades that began accumulating steadily. After a 19-win, 251 strikeout All-Star season in 1998, Pedro took back-to-back American League Cy Young awards in 1999 and 2000. He bounced back from injury in 2001 to win 20 games for the second time as a Red Sox ace in 2002. That initiated another run of four consecutive seasons with at least 14 wins and 200 k’s.
Pedro, like Wakefield, was a key member of the legendary 2004 Red Sox staff that came from behind 3-0 in the ALCS to eventually beat the rival Yankees and win the World Series, sweeping the Cardinals in four games. He was inducted into the Baseball Hall of Fame in Cooperstown on the first ballot for the class of 2015.
Before being drafted, Clemens showed flashes of brilliance at two storied Texas college programs, first at San Jacinto and then as the ace of the University of Texas Longhorns. He carried an almost immediate intimidating swagger that even Tiant or Jack Morris with the Tigers could not come close to.
After climbing in key stat departments during his first two seasons with the big club, Clemens rose to an elite level that had never been seen before at Fenway. A 24-win, 238-strikeout stat line that included an era title. He led the Red Sox, as the AL Cy Young and MVP in 1986, clear to the World Series. Of course, the World Series came out of reach heartbreakingly that season, but Clemens’s efforts and results were strong throughout the postseason.
While in Boston, Clemens won three of his seven career Cy Young awards. His 186 wins as a pitcher with the Red Sox are tied with Wakefield for second all-time, behind Cy Young himself. For many, Roger Clemens will always represent the face of the Boston Red Sox, a true warrior on the mound.
It is a shame that his reputation was later tarnished, but it should be noted that no erroneous accusations or attempts to smear his legacy have ever been made about his tenure as a Boston Red Sox pitcher. Using his time in Boston as a reference, “Rocket” Roger Clemens remains the greatest there ever was.
Of course, adding the great Cy Young among the top five greatest Red Sox pitchers would only seem right if one were to include the Deadball era. We will leave that debate to the historians. Among others who deserve honorable mention are Lefty Grove, Mel Parnell, Bruce Hurst, Curt Schilling, Rick Porcello, and David Price.
With the recent additions to the Boston Red Sox starting rotation, there could be some movement on this list as soon as this coming season. It will be challenging, though, to break any sense of loyalty that Fenway faithful will always have for these remarkable and incredibly accomplished pitchers.
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