From BR Bullpen
Jonathan Tyler Lester
- Bats Left, Throws Left
- Height 6' 2", Weight 190 lbs.
- High School Bellarmine Preparatory School
- Debut June 10, 2006
 Biographical Information
Pitcher Jon Lester was selected by the Boston Red Sox in the second round of the 2002 amateur draft. He had gone 4-2 with a 1.50 ERA his senior year of high school, striking out 86, walking 12 and allowing 19 hits in 42 innings. He was signed by scout Gary Rajsich for a $1 million bonus and made his pro debut later that summer with the GCL Red Sox, allowing five hits and six runs in 2/3 of an inning.
Lester went 6-9 with a 3.65 ERA for the 2003 Augusta GreenJackets. The next year, the southpaw had a 7-6, 4.28 line for the Sarasota Red Sox. At age 21, the Washingtonian hurler established himself as a prospect by going 11-6 with a 2.61 ERA and 9.89 K/9 for the Portland Sea Dogs. Baseball America named him the Red Sox minor league player of the year and the #4 prospect in the Eastern League, between Hanley Ramirez and Ryan Zimmerman. Lester led the EL in ERA by .30, struck out the most hitters in the league and tied for the lead with three complete games. He made the EL All-Star team, as the lefty pitcher and was named the league's Pitcher of the Year.
After a 3-4, 2.70 start to 2006 with the Pawtucket Red Sox, he made his big league debut as a member of the Boston rotation in June 2006. He went 7-2 with a 4.76 ERA in 15 starts with the club but was sidelined late in the season when he was diagnosed as having lymphoma.
After successful chemotherapy treatment, Lester was ready to return for the 2007 season, but with Boston's rotation adding Daisuke Matsuzaka and Jonathan Papelbon, Lester was presumed to be out of the running for a starting spot. He started the year in the low minors to regain his strength, then was promoted to AAA Pawtucket after three starts in A ball and one in AA. He went 4-5 with a 3.89 ERA in 14 starts for the PawSox before heading back to Boston, where he started another 11 games, with a 4-0 record and a 4.57 ERA. He made the postseason roster as a long reliever, pitching in two games against the Cleveland Indians in the ALCS. Starter Tim Wakefield was injured during that series, and Lester took his place in the rotation in the 2007 World Series. He started Game 4 in Coors Field, with the Red Sox leading the Colorado Rockies by three games to none. He pitched 5 2/3 scoreless innings, allowing only three hits, and was credited with the win as the Sox completed the sweep.
After spending the off-season hearing his name tossed about in a rumored trade which never materialized with the Minnesota Twins for ace left-hander Johan Santana, Lester made the Red Sox 2008 starting rotation out of spring training. In his 11th start, he threw a no-hitter against the Kansas City Royals on May 19, which was both the first complete game and shutout of his major league career.
Lester got off to a great start for Boston in 2013, going 4-0 in April while teammate Clay Buchholz went 5-0, a combined one-two punch that put the Red Sox in a surprising first place at the end of the month. On May 10th, he was outstanding in shutting out the Toronto Blue Jays on a one-hitter, the first of his career. He retired the first 17 batters before Maicer Izturis doubled in the 6th inning; he was the only batter to reach base, as Lester walked none. The Sox won the game, 5-0, and Lester improved to 5-0, 2.73 on the year. He was 15-8 for the season with a 3.75 ERA as the Red Sox went from last to first in the AL East. In the postseason, he recorded at least one win on all three rounds of the playoffs as the Red Sox defeated the St. Louis Cardinals in the 2013 World Series. He won both of his starts in the Fall Classic, with a sparkling 0.59 ERA, giving up only one run in 15 1/3 innings.
On May 3, 2014, he pitched one of the best games of his career, allowing only one hit while striking out a career-high 15 over 8 innings in a 6-3 Boston win over the Oakland Athletics. He was one of the few members of the Red Sox not to see his production go down significantly that season, and was named to the All-Star team for the third time. His record stood at 10-7, 2.52 after 21 starts, an even more impressive figure in light of the fact the Sox were in last place and well below .500. As he was about to hit the free agent market after the season, the Red Sox decided to cash in on his value by trading him to the Oakland Athletics along with OF Jonny Gomes on July 31st, obtaining another All-Star, OF Yoenis Cespedes, in return. He was a winner in his debut for the A's on August 2nd, benefiting from an eight-run 5th inning to defeat the Royals, 8-3. he did even better in his next start, on August 7th, pitching a three-hit shutout as he defeated the Minnesota Twins, 3-0. He was 6-4, 2.35 in 11 starts for Oakland, to end the season with a combined record of 16-11, 2.46, with 220 strikeouts in 219 2/3 innings. Manager Bob Melvin chose him to start the Wild Card Game against the Kansas City Royals on September 30. He was cruising along with a 7-3 lead entering the 8th inning, but he lost it quickly, allowing three of the first four hitters he faced that inning to reach base. All three eventually scored, and the Royals were able to tie the game in the 9th and win the wild contest in the 12th inning, 9-8.
Lester became a free agent after the 2014 season and was perhaps the most sought-after player on the market. The Red Sox made no secret that they wanted to bring him back to the fold, but he was also courted by a number of other teams. On December 9th, the Chicago Cubs were announced as the winners of the sweepstakes for his services, offering him a six-year contract worth $155 million.
Sources include 2003-2006 Baseball Almanacs
 Notable Achievements
- 2005 Pitcher of the Year Eastern League Portland Sea Dogs
- 3-time AL All-Star (2010, 2011 & 2014)
- AL Shutouts Leader (2008)
- 15 Wins Seasons: 6 (2008-2011, 2013 & 2014)
- 200 Innings Pitched Seasons: 6 (2008-2010 & 2012-2014)
- 200 Strikeouts Seasons: 3 (2009, 2010 & 2014)
- Won two World Series with the Boston Red Sox in 2007 and 2013