Jon Lester

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Jonathan Tyler Lester

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Biographical Information[edit]

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. He finished the season at 11-12, 3.34 in 32 starts, logging 205 innings and striking out 207 batters. He lost both of his starts in the postseason, however, one against the Los Angeles Dodgers in the Division Series and one against the New York Mets in the NLCS.

Lester was the National League Pitcher of the Month in June of 2016 when he went 4-0, 1.41 in six starts. On July 31st, he won a game with his bat, when he laid down a perfect squeeze bunt after being called on as a pinch-hitter with Jason Heyward on third base in the 12th inning of a game against the Seattle Mariners. Facing Cody Martin, he managed to lay down the ball just in front of home plate, which was enough to allow Heyward to score the winning run. He repeated as Pitcher of the Month in September, when he was 5-1, 1.48 in 6 starts. For the year, his record was a sparkling 19-5, 2.44. He led the league in winning percentage at .792, again pitched over 200 innings and struck out 197 opponents. He finished second in the voting for the 2016 National League Cy Young Award, behind Max Scherzer and ahead of teammate Kyle Hendricks. he was a key contributor to the Cubs first World Series title in 108 years as set the tone by winning Game 1 of the Division Series with 8 shutout innings against the San Francisco Giants on October 7th. After a no-decision in spite of an excellent start in Game 1 of the NLCS against the Los Angeles Dodgers, he won Game 5, 8-4. In the World Series against the Cleveland Indians, he lost Game 1 but came back to win Game 5, 3-2, on October 30th, with the Cubs facing elimination, and then came back to pitch 3 strong innings in relief in the decisive Game 7 on November 2nd. He left with two outs and a runner on second in the the bottom of the 8th, with the Cubs nursing a 6-3 lead, but Aroldis Chapman had a rare failure, giving up a run-scoring double to Brandon Guyer and a game-tying two-run homer to Rajai Davis. The Cubs eventually won the game in extra innings to end their record championship drought.

He had a tough first half in 2017, as he went only 5-6 for a Cubs team that was below .500 at the All-Star break. He was in good health, making a National League-leading 19 starts before the break, but the results left something to be desired as his ERA was 4.25. His start against the Pittsburgh Pirates on July 9th was particularly horrific, as he retired only two batters but gave up 10 runs on 6 hits and 3 walks. The highlight for the Pirates was a grand slam hit off him by Francisco Cervelli, although for the good of his annual stats, only 4 of the runs were earned. The Bucs went on to defeat the Cubs, 14-3, and Jon was charged with the loss. On August 1st, te one godawful hitter stunned everyone by homering off Patrick Corbin of the Arizona Diamondbacks. He also struck out 9 batters, including the 2,000th of his career, in what turned out to be a 16-4 Cubs win, but he did not pick up the victory as he was removed from the game after allowing the first three batters he faced in the 5th to reach base. He went 13-8, 4.33 on the year, pitching 180 2/3 innings. He also made three appearances in the postseason, and while he did not have a decision, he gave up just 3 earned runs in 14 1/3 innings. One of his appearances came in a rare relief outing, when he relieved Jake Arrieta after 4 innings in Game 4 of the NLDS on October 11th and held the Washington Nationals to one run on one hit in 3 2/3 innings. The score was still just 1-0 in favor of the Nats when he left the game, but the runner who was on base came in to score as Washington added four runs against three different pitchers before the final out of the inning could be recorded, and the Cubs lost, 5-0. Earlier in that inning, he had picked Ryan Zimmerman off first base after a walk, a sign that while baserunners could take unusual liberties with their lead given his reluctance to throw to first base, he could still catch those who went way too far.

He got off to a good start in 2018 as at the end of May, he was 5-2, 2.71 in 11 starts. He then kicked it up a gear in June as he did not give up a run in his first two starts of the month, both wins, totaling 14 inning. In the second of these, on June 9th, he gave up just one hit over 7 innings against the Pirates, on his way to combining with two relievers on a one-hitter in a 2-0 victory. He was the NL Pitcher of the Month in June when he went 5-0, 1.13; it was already his sixth time winning the award. He finished that season at 18-6, 3.32, leading the league in wins and finishing 9th in the voting for the Cy Young Award. However, the season ended in disappointment for him and the Cubs: he was the starter in the Wild Card Game against the Colorado Rockies on October 2nd, one day after Chicago had lost a one-game playoff against the Milwaukee Brewers that could have given them the best record in the NL, an honor which instead went to Milwaukee. He pitched well against Colorado, giving up just 1 run in 6 innings while striking out 9, but the Cubs lost the game in extra innings, 2-1, and their season ended then and there.

In 2019, Lester fell to 13-10, 4.46 as his ERA rose by more than a full run compared to the previous season. He continued to take his turn in the rotation every fifth day, making 31 starts, but he logged only 171 2/3 innings, as his inability to pitch deep into games cost him. He also gave up a league-leading 205 hits, a very high total given he was far from the league leaders in innings pitched. The shortened 2020 season was not any better, as his ERA continued to rise, to 5.16, and he ended up with a record of 3-3 in 12 starts. The Cubs finished on top of their division, but he was not given a start in the postseason, when they were upset by the Miami Marlins in two games in the Wild Card Series.

Lester became a free agent following the 2020 season and signed with the Washington Nationals on January 27, 2021 after finding out that there was only limited demand for his services, most teams having decided that he had reached the end of the line. He made 16 starts for the Nats in the first half of the season, and the results were in line with his most recent work, with an ERA of 5.02 and a record of 3-5. On July 30th, he was traded to the St. Louis Cardinals as part of the Nationals' mid-season fire sale that saw just about every veteran on the team be sent to another team. In his case, the trade netted Washington marginal OF Lane Thomas. He pitched a lot better with his new team, however, going 4-1 in his first 10 starts, with an ERA of 4.02, just as the Cardinals were climbing their way back into the wild card race after having been left for dead at the All-Star break. On September 20th, in the 10th of these starts, he recorded the 200th win of his career in a 5-2 win over Milwaukee that was also the 9th straight for St. Louis, consolidating the team's position as the second wild card. He finished the season with a combined mark of 7-6, 4.71 in 28 starts. On January 12, 2022, he announced his retirement after 16 major league seasons.

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 does not like to issue an intentional walk; he has the lowest rate of IBB of any modern starting pitcher by a wide margin. At the end of the 2016 season, he had issued a total of 4 intentional walks in his career, or one per 79 starts; next stingiest was Brad Radke, with one every 31 starts. He was also known for a time 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. But once he got the first hit out of the way, it seemed to break a mental barrier and he had a total of 4 in in 2015 and 6 in 2016, nothing great but not extraordinarily bad either. He was also used as pinch-hitter for his bunting ability, as noted above, having picked up a respectable total of 16 sacrifice hits over the two seasons.

Lester named his daughter, born a few weeks after the Cubs' historic World Series win in 2016, Cy Elizabeth, although he was quick to point out that the name had nothing to do with Cy Young.

Sources include 2003-2006 Baseball Almanacs

Notable Achievements[edit]

  • 2005 Pitcher of the Year Eastern League Portland Sea Dogs
  • 5-time All-Star (2010, 2011, 2014, 2016 & 2018)
  • 2016 NLCS MVP
  • NL Wins Leader (2018)
  • NL Winning Percentage Leader (2016)
  • AL Shutouts Leader (2008)
  • 15 Wins Seasons: 8 (2008-2011, 2013, 2014, 2016 & 2018)
  • 200 Innings Pitched Seasons: 8 (2008-2010 & 2012-2016)
  • 200 Strikeouts Seasons: 4 (2009, 2010, 2014 & 2015)
  • Won three World Series with the Boston Red Sox (2007 & 2013) and the Chicago Cubs (2016)

Further Reading[edit]

  • Jay Cohen (Associated Press): "Cubs LHP Jon Lester working on unusual bounce throw to bases", USA Today Sports, March 5, 2018. [1]
  • Mark Feinsand et al.: "Roundtable: Is Jon Lester a Hall of Famer?",, January 12, 2022. [2]
  • Bob Nightengale: "Years after divorce with Red Sox, Jon Lester has 'meant everything' to Cubs", USA Today, March 27, 2019. [3]

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