Roger Clemens – No. 21
This one may be the most controversial selection on this list. The Rocket always had a prickly personality and didn’t win himself any more fans in Boston after he left the Red Sox. Factor in that his connection to the PED scandal has thus far kept him out of Cooperstown and you can see why the team would be hesitant to retire his number
They shouldn’t be. Clemens is tied for first in franchise history with 192 wins and produced a 76.8 WAR during his time in Boston, which leads the all-time Red Sox leaders for pitchers by a mile. He collected three Cy Young awards in Boston and won an MVP in 1986. He had seven straight seasons in which he pitched well over 200 innings, including five where he topped 250 innings.
Among his impressive accomplishments is a 20 strikeout performance in a dominant outing against the Seattle Mariners in 1986 to set a major league record. He would later tie his own record in 1996 against the Detroit Tigers. To this day Clemens is still the only pitcher to have done that twice.
The Texas native became one of the team’s most hated rivals when he joined the Yankees, but we can’t really fault him for that considering it was then-general manager Dan Duquette that let Clemens get away after the 1996 season, deeming him to be in the “twilight of his career.” Back-to-back Cy Young awards that Clemens won with the Toronto Blue Jays immediately after he moved on proved that assessment wrong, while he would have many more productive years in a career that spanned 24 seasons. While he accomplished a great deal after leaving Boston, that doesn’t erase what he did in the 13 years here with the Red Sox.
Clemens may not be everyone’s favorite person, but he is certainly the most productive pitcher this franchise has ever seen. The Red Sox buried the hatchet by inducting Clemens into the franchise Hall of Fame in 2014. The next step needs to be retiring No. 21.
Next: David Ortiz