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The top four starters in Red Sox history are clear: Roger Clemens, Cy Young, "Smoky" Joe Wood and Pedro Martinez.
Some Sox fans may want to deduct points from the Rocket because of his time in pinstripes, but he and Young belong at the top of the all-time Red Sox rotation. In fact, a strong case can be made that either Young or Clemens is the best pitcher in baseball history.
Young and Clemens put up strikingly similar numbers in several respects as members of the Red Sox. Young's 511 career wins are the most in baseball history by a wide margin, but he (192-112) and Clemens (192-111) have nearly identical win-loss records as members of the Red Sox franchise. Each also threw 38 shutouts while pitching approximately 2,700 innings for Boston.
There are of course some differences as well. Young bests Clemens by more than a full run in ERA (2.00 to 3.06), but Clemens pitched in a much more hitter-friendly era and nearly doubled Young's strikeout total (2,590 to 1,341) in less than 50 more innings. Clemens, you may recall, twice set the record for strikeouts in a game with 20.
While Young and Clemens mixed dominance with longevity, Wood and Martinez had several seasons in a Boston uniform that were every bit as dominant, if not more so.
Wood made all but one of his 158 career starts for the Red Sox, and ended up with 117 wins, 56 losses and a team record 1.99 ERA. Just as Tris Speaker's best year was Fenway Park's first, so it was for Wood. His 1912 season was one for the record books, as he finished with a 34-5 record to go along with a 1.91 ERA.
Like Clemens, Martinez played in a much more hitter-friendly (and pitch-count friendly) era, but he also had some special seasons in Boston. Martinez was utterly dominant in 1999, going 23-4 with a 2.07 ERA and 313 strikeouts in just 213.1 innings. He followed that up with another incredible year, going 18-6 with a 1.74 ERA and 284 Ks. Then, after missing much of 2001 with a rotator cuff injury, Martinez bounced back with a 20-4 record, 2.26 ERA and 239 Ks in 2002.
During his seven seasons in Boston, Martinez put up a 2.52 ERA and matched Wood's 117 wins, while losing just 37 games.
The fifth spot in the Red Sox all-time rotation is a difficult choice between several truly outstanding pitchers.
Dutch Leonard, Carl Mays and some guy named Ruth each pitched over 1,000 innings for the Red Sox in the late 1910's with ERAs at or below 2.21. With those three guys anchoring the rotation, it's no surprise the Red Sox won the World Series in 1915, 1916 and 1918.
Lefty Grove also had several dominant seasons in Boston, but most of his absolute best years were as a member of the Philadelphia Athletics. Mel Parnell does not get full due for his excellent pitching in the late '40's and early '50's. Parnell, who played his entire career in Boston, won 18 or more games four times in a five year stretch from 1949-1953, and finished with a very solid 3.50 ERA in a fairly strong hitters era.
But the fifth spot ultimately must go to El Tiante, Luis Tiant. After suffering injuries in consecutive years with the Indians and Twins that many believed would end his career, Tiant returned with a bang for the Red Sox, putting up a 15-6 record and 1.91 ERA to win the AL Comeback Player of the Year award in 1972. Tiant would go on to win 20 or more games three times over the next four years. All told, during his eight seasons in Boston, Tiant won 122 games with a 3.36 ERA.