Jon Lester (2002, 2nd round)
The Red Sox have drafted premium talent over the years but their track record developing pitchers leaves a lot to be desired. Spoiler alert, there aren’t many pitchers on this list and none whom the Red Sox have drafted since Jon Lester in 2002 appear to be close to entering the conversation.
Lester made his major league debut in 2006 and was a vital part of a championship team the following season, tossing 5 2/3 shutout innings to earn the win in the decisive Game 4 of the 2007 World Series.
Over parts of nine seasons in Boston, Lester went 110-63 with a 3.64 ERA, 1.28 WHIP, and 8.3 K/9. He made a pair of All-Star appearances and finished as high as fourth on the Cy Young ballot.
The postseason is where Lester shined the brightest and where he developed his reputation as a big game pitcher. He pitched brilliantly during Boston’s run to a World Series championship in 2013, going 4-1 with a 1.55 ERA in five postseason starts.
Boston’s brass misplayed their hand in contract negotiations prior to the 2014 season, leading to a mid-season trade that sent Lester to the Oakland A’s once the Red Sox fell out of contention and it was clear an extension couldn’t be reached. They tried to bring him back in free agency but couldn’t match the steep price the Chicago Cubs were willing to pay.
Lester went on to bring a championship to Chicago and is still going strong in a Cubs uniform but we’ll never forget what he did for us in Boston.