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. He was named the Cubs opening day starter on April 5, 2015, but lost to the Cardinals, 3-0, as he gave up 3 runs on 8 hits in 4 1/3 innings. The concerns grew as after three starts, his record stood at 0-2, 6.89, after he had complained of a "dead arm" in spring training, far from what the Cubs were expecting from a putative ace. The poor results also highlighted another issue, which was that Lester had seemingly lost the ability to throw to first base at some point, not having made a single pick-off attempt since 2013. He made a couple of attempts during his second start with the Cubs, but both were awful, and there was concern that now that this was known, it was an open invitation for baserunners to take liberties against him. The problem extended to throwing to any base after fielding a batted ball as well, but on April 19th, he made nice play when such a ball hit by Clint Barmes of the San Diego Padres got stuck in the webbing of his glove, and he just tossed the whole thing to 1B Anthony Rizzo to record the out. He recorded his first win for the Cubs on May 1st thanks to a brilliant performance that saw him shut down the Milwaukee Brewers for 7 innings before handing the ball to the bullpen, who completed the 1-0 win. He was 4-2 after a 4-1 win over the Pittsburgh Pirates on May 16th, his fourth straight winning start, but was then winless until the All-Star break, a total of 10 starts during which he went 0-6, the longest such streak of his career. He recovered in his first start after the break, on July 18th, as he did not give up a hit to the Atlanta Braves until an 8th-inning single by A.J. Pierzynski and he ended up a 4-0 winner. Two starts earlier, he had taken a no-hit bid into the 7th inning against the St. Louis Cardinals on July 6th, but had ended up losing that game. On August 24th, he came within one out of pitching his first complete game and shutout for the Cubs, but he gave up a game-tying single to Carlos Santana of the Indians with two outs in the 9th; Hector Rondon then came on to register the final out of the inning and vultured a win when Kris Bryant homered in the bottom of the frame. On September 15th, he did pitch his first complete game as a Cub in a key match-up against the Pirates, ending up a 2-1 winner as Chicago salvaged a doubleheader split. He set a new Cubs record for strikeouts by a lefthanded pitcher when he recorded number 203 on September 30th; Ken Holtzman had set the previous record in 1970.
Lester's repertoire includes a 94-97 mph fastball, 88-92 mph cutter, mid 70's curveball, occasional slider or changeup. In addition to his woes on pick-off attempts, he is known as one of the weakest hitters in major league history. On May 27, 2015, he set a new record for futility when he extended his hitless streak from the start of his career to 59 at-bats; the previous record holder was Joey Hamilton, with 57. He finally managed to get his first hit on July 6th, an infield single off John Lackey of the St. Louis Cardinals, after having pushed his streak of hitless at-bats to 66.
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: 7 (2008-2010 & 2012-2015)
- 200 Strikeouts Seasons: 4 (2009, 2010, 2014 & 2015)
- Won two World Series with the Boston Red Sox in 2007 and 2013