Jon Lester was selected by the Red Sox in the second round of the 2002 June Amateur Draft out of Bellarmine High School in Tacoma, Washington and reached the majors in June 2006.
He suffered a potentially career-altering setback in September 2006 when he was diagnosed with non-Hodgkin’s lymphoma.
Lester recovered in time to make 12 appearances and 11 starts for the Red Sox during the second half of the 2007 season and started the World Series-clinching Game 4 against the Colorado Rockies in October.
From there, Lester emerged as one of the top left-handed starters in baseball, earning three All-Star bids with the Red Sox, finishing fourth in the Cy Young voting in 2010 and throwing a no-hitter at Fenway Park in May 2008.
He was traded to the Oakland Athletics at the non-waiver deadline in July 2014 and signed as a free agent with the Chicago Cubs that December.
In parts of nine seasons with Boston, Lester was 110-63 with a 3.64 ERA and 1.287 WHIP in 1,519.1 innings, an ERA+ of 120 and 1,386 strikeouts. He appeared in 242 games, all but one as a starter, and led the American League in strikeouts per nine innings in 2010.
Lester was part of two World Series winners, 2007 and 2013, and in four postseasons for the Red Sox was 6-4 with a 2.13 ERA and 1.050 WHIP in 76.2 innings, striking out 68. He started 11 games and worked in relief twice against the Cleveland Indians in the 2007 ALCS.
Lester is under contract with the Cubs through 2020, with a team option/buyout for 2021 that becomes guaranteed based on innings pitched in 2020 or 2019-20.