Boston Red Sox: Ten Greatest Starting Pitchers of All-Time

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#2: Roger Clemens

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With a blazing fastball that reached triple-digits at times, Roger Clemens made his big league debut with the Red Sox in May of 1984. While he immediately showed his elite stuff, Clemens’ first two big league seasons were up-and-down. However, it only took until 1986 when Clemens exploded onto the scene to begin a dominant MLB career.

Early in his incredible 1986 season, Clemens became the first MLB pitcher to record 20 strikeouts in a nine inning game, in an April match-up at Fenway Park against the Seattle Mariners. That was just the beginning of one of the most dominant pitching seasons of all-time.

At only 23-years-old, Clemens became the best pitcher in baseball in 1986, going 24-4 with a 2.48 ERA and 238 strikeouts for the World Series appearing Boston Red Sox. Clemens led the league in wins, winning percentage and ERA that season, and was not only named the Cy Young award winner, but was also the first pitcher to win the MVP award since 1971.

Clemens continued his domination in 1987, leading the league with 20 wins and taking home another Cy Young award.

Possibly one of the best pitching talents the game had ever seen before, Clemens continued to have a ton of success. He led the league in ERA for three consecutive seasons from 1990-1992, with his 21-6, 1.93 ERA performance in 1990 allowed for a second place Cy Young finish and third place in MVP voting.

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Clemens won his third Cy Young award with the Red Sox in 1991, when he led the league in ERA (2.62), innings pitched (271.1) and strikeouts (241). After another dominant 1992 season, Clemens had an up-and-down few years with the Red Sox. However, late in the 1996 season, Clemens put up another 20 strikeout performance, and is still the only player in MLB history to have accomplished that feat twice.

That 20 strikeout game ended up being the third to last start in Clemens’ career with the Red Sox, as he left the team via free agency in the off season. The Red Sox tried hard to resign Clemens, but he signed with the Toronto Blue Jays instead.

Clemens only spent two years with the Blue Jays, but he forced the Red Sox to have a close look at what they were missing. In arguably the best two-year run for a pitcher of all-time, Clemens won the pitching Triple Crown (league leader in wins, ERA and strikeouts) in back-to-back seasons with the Blue Jays. Obviously taking home his fourth and fifth Cy Young awards as well.

Clemens went on to have a dominant career with the New York Yankees and Houston Astros after his two years in Toronto, pitching well into his 40s and picking up two more Cy Young awards.

Clemens is commonly looked at as the one who got away from the Red Sox, and while he was incredible, it is not like he lead them to any success. The Red Sox only reached the post season four times in Clemens’ 13 years with the team, reaching the World Series only once. Clemens was obviously incredible, but does keeping him around really change the course of Red Sox history?

His 13 years with Boston were among the greatest of his career, and he left the organization tied as the team leader with 192 wins, and the lone all-time strikeout leader with 2,590. If you only consider statistics (obviously, I do not), Clemens is probably the best pitcher in the history of the Red Sox. His longevity of domination is unmatched, but his lack of post season success, and later controversy certainly comes into play.

Controversy clouded the later stages of Clemens’ career, and despite being arguably the best pitcher of his generation, he has yet to receive the Hall of Fame nod. It may be unlikely that he ever reaches the Hall, but if he does, based on body of work, Clemens should go in as a member of the Red Sox.

Next: The GOAT