Number Seven: Jon Lester
Failing to re-sign Jon Lester may be the greatest mistake in Red Sox history. During his nine years in Boston, Lester garnered the love and respect of Red Sox fans, and rightly so. The left-hander earned a reputation as one of the best pitchers in baseball, recording a record of 110-63, an ERA of 3.58, and 1386 strikeouts.
Lester also played a key role in two World Series victories. During Game 4 of the 2007 World Series, Lester made his first playoff start. He allowed only three hits, leading the Red Sox to victory, and becoming the third pitcher in World Series to clinch a series on his first playoff start.
Then, in 2013, as the team’s ace, Lester led the Red Sox to the World Series, and a victory in Game One.
With two World Series rings, three All-Star selections, and phenomenal stats, Lester easily makes it onto our list.
Next: Curt Schilling