5 Greatest Boston Red Sox Pitchers of All Time

The Boston Red Sox are American League originals. They entered Major League Baseball in the AL in 1901 alongside the Chicago White Sox, Minnesota Twins, Detroit Tigers and now-Cleveland Guardians. As such, their history is deep and impressive, even counting the long World Series drought.

Three of the most famous pitchers to ever play the game played for the Red Sox and you’ll find them here as the top three pitchers in franchise history. But when it comes to picking the other two of the greatest five, pickings were tougher. Not because there weren’t options, but because there were almost too many.

With that in mind, here’s our list of the five greatest Red Sox pitchers of all-time.

5. Smoky Joe Wood

It’s been a few decades now that the word “smoke” has come into the vernacular as a consensus word for “fast” or “hard.” It’s been around a lot longer. In fact, Wood, whose name is just “Joe Wood,” may have created it.

Walter Johnson, who many consider the greatest pitcher in the history of the game, once said, “Listen, mister, no man alive can throw harder than Smoky Joe Wood.” 

Wood came up with the Sox for two starts in 1908 before establishing himself the following season as a regular and played eight seasons with Boston before a contract dispute saw him out of the 1916 season and sold to Cleveland ahead of 1917. But by that time, his arm, with all that smoke, was, well, toast.

But in those years with the Sox, Wood was brilliant, especially in 1912. That year, he finished 34-5 with a 1.91 earned-run average and recorded a Major League-high 35 complete games with 10 shutouts en route to a fifth-place finish in Most Valuable Player voting. And although he never quite put up those kinds of totals again, Wood’s tenure will remain legendary for its short sweetness.

4. Lefty Grove

When Grove arrived in Boston in 1934, he looked finished. He was 34 years old and while he was glamorous with Philadelphia Athletics in his first nine years, even winning an MVP award in 1931, that first season with the Red Sox was miserable. Grove started just 12 of his 22 games and recorded a 6.50 ERA while giving up more than 12 hits per nine innings.

Something happened that offseason. Grove made the next five All-Star Games and led all of baseball in WAR each year from 1935 to 1937, putting up ERAs of 2.70, 2.81 and 3.02. Those first two totals led the American League, as did his WHIP totals of 1.223 and 1.192 in those seasons.

Grove kept things at a high quality through 1940, though by that point he was starting just over 20 games a season. And while he never quite managed to reach the highs with the Sox as he did with the As, Grove remains the franchise’s No. 4 pitcher in career WAR.

3. Cy Young

Like Grove, Young joined the Red Sox for the second half of his career, landing in Boston in 1901 as a 34-year-old. He had already established himself as a great after nine seasons with the Cleveland Spiders and two with the St. Louis Cardinals. But he wasn’t done in Boston.

In fact, Young’s first season with the Red Sox was the best of his career. He went 33-10 with a 1.62 ERA and 185 strikeouts and a 0.972 WHIP. All of those totals led the American League and his 12.4 WAR led all of baseball. 

There were no All-Star Games at the time, but Young retired after the 1911 season with two ERA titles, a triple crown win and the 1903 World Series. Most famously, the award given to the best pitcher in each league every season is now named the Cy Young Award.

2. Pedro Martinez