Jon Lester

The Red Sox selected Lester in the second round, with the 57th overall selection, of the 2002 Major League Baseball draft and gave him the highest signing bonus of any second-rounder that year, $1 million.

Lester quickly moved through the Red Sox organization, posting an 11–7 win–loss record, a league-leading 2.61 earned run average (ERA) and a league-best 163 strikeouts for the Portland Sea Dogs of the Class AA Eastern League in 2005. He was named the Eastern League Pitcher of the Year and Red Sox Minor League Pitcher of the Year and was selected as the left-handed pitcher on the Eastern League's year-end All-Star team and on the year-end Topps Class AA All-Star squad.

Lester was one of the Red Sox' top-rated prospects while in the minors, and other major league teams made efforts to acquire him. The Texas Rangers had demanded Lester be part of the proposed but ultimately rejected deal before the 2004 season for Alex Rodriguez.[2] The Florida Marlins insisted he be included in the trade for Josh Beckett before the 2006 season, but again, the Sox were able to keep Lester.[3]

With a rash of injuries and general ineffectiveness of several Red Sox starters, the team recalled Lester on June 10 to make his major league debut against the Texas Rangers. He put up a 7–2 record and a 4.76 ERA in ​81 ¹⁄₃ innings pitched in his rookie year.

On August 27, 2006, Lester was scratched from his scheduled start against the Oakland Athletics due to a sore back. The following day he was placed on the 15-day disabled list, and was sent back to Boston for testing. At the time, Lester's back problems were thought to be the result of a car crash he was involved in earlier in the month. On August 31 it was reported that Lester had been diagnosed with enlarged lymph nodes and was being tested for a variety of ailments, including forms of cancer.[4] A few days later, doctors at Massachusetts General Hospital confirmed that Lester had a treatable form of anaplastic large cell lymphoma.[5] Lester underwent off-season chemotherapy treatments at Seattle's Fred Hutchinson Cancer Research Center. In December 2006, ESPN.com reported that Lester's latest CT Scan showed no signs of the disease, which appeared to be in remission.

Lester before Game 4 2007 World Series

Following the successful treatment of his lymphoma, Lester was able to return to the Red Sox midway through the 2007 season. Lester attended spring training in 2007, and started the season for the class A Greenville Drive. Lester then started for Triple-A Pawtucket Red Sox in late April 2007.[6] In June, Lester was removed from the disabled list, and sent to Pawtucket for further rehab outings.[7]

Lester made his first 2007 start for the Boston Red Sox on July 23 against the Cleveland Indians at Jacobs Field in Cleveland, pitching 6 innings, allowing 2 runs on 5 hits and struck out 6, picking up the win. On September 26 against the Oakland Athletics at Fenway Park, Lester gave up what would turn out to be the final career home run by Hall of Fame catcher Mike Piazza. In the 2007 World Series against the Colorado Rockies, Lester won the series-clinching Game Four for the Red Sox, pitching 5⅔ shutout innings, giving up three hits and three walks while collecting three strikeouts. Lester became the third pitcher in World Series history to win a series clinching game in his first post-season start.

To honor Lester's comeback from lymphoma, the Boston Baseball Writers' Association of America voted him the 2007 Tony Conigliaro Award.[8]

On May 19, 2008, Lester threw a no-hitter in a 7–0 win against the Kansas City Royals.[9] It was the 18th no-hitter in Red Sox history. Lester threw 130 pitches in the game, allowing only two walks and striking out nine batters, and was charged with a throwing error on a pickoff attempt in the second inning. It was the first no-hitter thrown by a Red Sox left-handed pitcher since Mel Parnell in 1956, the first in MLB since teammate Clay Buchholz in September 2007, and the MLB-record fourth no-hitter caught by Jason Varitek. It was also only the second no-hitter ever pitched against the Royals; Nolan Ryan pitched the other in 1973.[10][11]

In 2008, Lester went 16–6 with a 3.21 ERA. Along with his no-hitter, he pitched a five-hit shutout in his first start at Yankee Stadium. He was named the AL Pitcher of the Month in July and September. Lester was also a key figure in the Red Sox' victory over the Angels in the American League Divisional Series, pitching 14 innings without allowing an earned run. Lester had the second highest winning percentage of all starting pitchers over the last three years (27–8, .771), and led the Red Sox in innings pitched in 2008 with 210.3.[12][13]

Lester's losses in Games 3 and 7 of the 2008 ALCS were the first losses he had ever had in consecutive starts.[14]

Lester also received the 2008 Hutch Award, given to the Major League player who "best exemplifies the fighting spirit and competitive desire" of Hutchinson.[15][16]

On March 8, Lester agreed to a five-year, $30 million contract extension with a $14 million team option in 2014.[17]

The season started poorly, with him allowing 11 runs and getting losses in his first two starts.[18] This was the first time he lost in consecutive regular season starts. He began to pitch very well in late May, going 12–3 with a 2.31 ERA in his final 22 starts. On June 6, Lester made his bid for a second no-hitter against the AL West-leading Texas Rangers at Fenway. He pitched 6​¹⁄₃ perfect innings, striking out 10 batters, on 61 pitches through the first six innings. Michael Young hit a one-out double to left center field in the seventh inning to break up the no-hitter, but Lester pitched a complete game, striking out a total of 11 batters, giving him 23 Ks in two starts (he had a career-best 12 Ks his previous start). On August 14, Lester struck out ten batters for the sixth time in the 2009 season, the most times ever by a Red Sox left-handed pitcher. He had never done it before that season. Lester started 32 games in 2009, going 15–8 with a 3.41 ERA.

Lester started Game One of the 2009 ALDS against the Los Angeles Angels of Anaheim, but the Red Sox lost the game 5–0 and would eventually be swept in the series.[19]

In 2010 Lester won his final start in April, then won five of the six games he started in May. Lester went 5–0 with a 1.84 ERA and 45 strikeouts and was named the American League Pitcher of the Month, winning the award for the third time.

On June 16 he got his 50th career win, against the Arizona Diamondbacks. Lester was selected to the American League All-Star team on July 1, this was his first selection. At the time of the break he was 11–3 with a 2.78 ERA and 124 strikeouts. He pitched the sixth inning for the AL allowing no baserunners.

On July 25 he took a perfect game into the sixth inning against the Seattle Mariners but lost it in that inning due to an error made by Eric Patterson. A home run by Michael Saunders broke up the no hit bid. The Red Sox eventually lost the game. The loss was the second of four losses in a row Lester took after the All-Star break. He would eventually turn it around throwing 6 shutout innings against the Yankees and then 8 shutout innings, despite feeling sick, against the Rangers. Lester finished the season strong, developed an excellent pickoff move, but fell just short of 20 wins.

Lester finished the season T-4th in wins (19) and in 4th place in strikeouts (225) in the Majors (AL and NL combined) in 2010. He finished 25th in the Major Leagues with a 3.25 ERA in an above average year for pitchers. Lester finished fourth in voting for the 2010 AL Cy Young Award as well.

In 2011, Lester was the opening day starter for the Red Sox, on the road against Texas. He had a solid season, leading Boston's rotation in wins for the second year in a row and strikeouts for the third year in a row. He was named to the American League All-Star team, replacing Felix Hernandez, but did not pitch due to a lat injury.

Lester struggled along with the rest of the team, losing his last three decisions, including giving up eight runs in a start against the New York Yankees. He pitched the season finale against the Baltimore Orioles, pitching six innings and giving up just two runs. The bullpen was unable to hold onto the lead, and the Red Sox were eliminated. Lester finished the season 15–9 with a 3.41 ERA. He finished in the top 20 in strikeouts (11th), wins (10th) and ERA (17th).

In the end of the 2011 season, Lester and two more starting pitchers were in a center of a controversy that told that the three (and sometimes more) drank alcohol during games. Many people hypothesized that this was part of the reason why the Red Sox went 7–20 in September and were eliminated on the last day of the season. Lester was the first to tell what really happened, and stressed that they would only drink when they weren't pitching for that day. Lester was the first of the three starting pitchers to admit to his drinking.[20]

The line score inside Fenway Park following Jon Lester's no-hitter, May 19, 2008

In 2012, Lester was again the opening day starter for the Red Sox. Lester's season was very disappointing, posting a 9–14 record, a sub-par 4.82 ERA, and a .273 batting average against.

On May 10, 2013, Lester threw a complete game one-hitter, with no walks, against the Toronto Blue Jays, facing just 28 batters.

On October 3, 2013, Lester was named as the starting pitcher for the 2013 ALDS against the Tampa Bay Rays in the Red Sox first return to the postseason since 2009. The following day, Game 1 of the ALDS took place at Fenway Park with Lester pitching ​7 ²⁄₃ innings with three walks and striking out seven and the Red Sox winning 12–2 (and winning the series 3–1). Lester also tied Josh Beckett's Red Sox Postseason record of 4K's of the first four batters to begin the game. Lester started Game 1 of the 2013 ALCS against the Detroit Tigers on October 12, 2013. He pitched ​6 ¹⁄₃ innings with four strikeouts and allowed one run, but was outmatched by a one-hit game put together by the Tigers' pitching staff led by starter Aníbal Sánchez. At Comerica Park on October 17, 2013, Lester again faced Sanchez in Game 5. The Red Sox won 4–3 with Lester pitching 5 innings and showing spectacular defensive skills in the 5th inning throwing out former teammate Jose Iglesias with a glove flip to first base on a bunt attempt.

After the Red Sox victory in the ALCS, Lester was selected to start Game 1 of the 2013 World Series against the St. Louis Cardinals. Lester pitched to an 8–1 victory over St. Louis starter Adam Wainwright. Lester then went on to a Game 5 win again over Wainwright giving the Red Sox a series lead of 3–2. The Red Sox won the series in six games.

On May 3, 2014, Jon Lester pitched 8 one-hit innings against the Oakland Athletics, where he had a career-high 15 strikeouts. It was the most by a Red Sox pitcher since Josh Beckett in 2010.

He was elected to his third all-star game in July 2014 after posting a 2.73 ERA over his first 18 starts of the season.[21]

On July 31, 2014, Lester and Jonny Gomes were traded to the Oakland Athletics for Yoenis Céspedes and a competitive round 2015 draft pick. The move reunited Lester with former teammates Jed Lowrie, Coco Crisp, Brandon Moss and Josh Reddick.[22] He won his debut start against the Kansas City Royals on August 2.[23] He had a 6–4 record and a 2.35 ERA, while pitching for the A's.

In July, Lester made a cameo in the Air Jordan Re2pect Commercial honoring Derek Jeter. Lester is shown tipping his hat to the Yankees' captain, the first to do so in the commercial.

Lester was the starting pitcher for the A's in the Wild Card game, against the Kansas City Royals. He left the game after pitched ​7 ¹⁄₃ innings with the Athletics leading 7-4. Lester, however, received no decision, as the bullpen blew the lead and Kansas City Royals made a dramatic comeback to win the game in 12 innings.

Lester had a 16–11 record with a 2.46 ERA and finished 4th in the AL Cy Young voting.

In December 2014, Lester agreed to a six-year, $155 million deal with the Chicago Cubs with a vesting option for a seventh year at $15 million.[24][25]

Lester made his first start for the Cubs during opening night on April 5, 2015 against the St. Louis Cardinals. He pitched 4.1 innings allowing 3 runs as the Cubs were shut out by the Cardinals 3–0.[26] He finished the month of April with a record of 0–2 and an ERA of 6.23 in 21.2 innings pitched with 24 strikeouts and 5 base-on balls.[27]

On May 27, 2015, matchup with the Washington Nationals, Lester hit a fly ball to deep center field that nearly eluded Denard Span. Span caught the fly ball to end the inning, bringing Lester to a record-setting 0-for-58 to start his career.[28] On July 6, 2015, Lester recorded his first career major league hit against John Lackey of the St. Louis Cardinals after starting his career 0-for-66 as a hitter.

Lester posted an 11–13 record, logging 205 innings pitched with an ERA of 3.34 in his first year with the Chicago Cubs. He led the major leagues in stolen bases allowed, with 44.[29]

On October 9, he was the losing pitcher in Game One of the NLDS versus the St. Louis Cardinals. On October 17, he took another loss in Game One of the NLCS versus the New York Mets.

On July 31, 2016, against the Seattle Mariners, Lester came off the bench in the 12th inning and laid a bunt down to score the winning run. On a 2-2 pitch with one out and Jason Heyward and 3rd, Lester capped off a wild comeback for the Cubs, who were down 6-0 in the 3rd inning and going into the 7th.

In 2016, Lester finished second in the NL with 19 wins, matching his career high. He was also second in ERA (2.44). He led all major league pitchers in left on base percentage, stranding 84.9% of base runners.[30]

Lester started Game 1 of the 2016 NLDS against the San Francisco Giants. He earned the win after tossing eight scoreless innings, the Cubs would go on and win the series 3 games to 1.

Lester pitching in 2016 World Series

Lester also started Game 1 of the 2016 National League Championship Series against the Los Angeles Dodgers, he pitched six innings and allowed just one run and had a no-decision. He also started Game 5 of the series and pitched 7 innings of one run ball, earning his third win of the postseason. The Cubs would go on and win the series 4 games to 2. Lester was named Co-MVP of the 2016 NLCS along with Javier Báez. Lester's performance helped propel the Cubs to the World Series for the first time since 1945.

Lester was named the Game 1 starter of the 2016 World Series against the Cleveland Indians, where he took the loss after throwing 5.2 innings and allowing 3 runs. Lester also started Game 5, allowing just 2 runs in 6 innings, leading to a 3–2 Cubs victory to extend the series. Lester pitched in relief in game 7, which the Cubs won to win their first championship in 108 years.[31]

On August 1, Lester recorded his 2,000th career strikeout, and also hit his first career home run.[32] On August 18, Lester was placed on the 10-day disabled list due to left shoulder fatigue.[33]

Lester at the 2018 Major League Baseball Home Run Derby

During spring training, Lester was announced as the Opening Day starter for the Cubs.[34] On July 1, 2018, Lester hit his 2nd career home run, a three-run shot, off of Lance Lynn in an 11-10 win over the Minnesota Twins.

Owning an 11-2 record with a 2.25 ERA, Lester was named to the 2018 MLB All-Star Game, although he was not able to participate and was replaced by Zack Greinke due to the fact that he had pitched on the Sunday before the game.[35] For the season he was 18-6 with a 3.32 ERA.

Lester was named the Opening Day starter for the third consecutive year and the eighth time in his career. He earned the win in a 12-4 Cubs victory against the Texas Rangers. On August 6, 2019, he called himself the “Weakest Link” in the Cubs rotation by giving up a career high, 11 runs in a 11-4 loss to the Oakland Athletics.[36]

Lester has had well-documented problems throwing the ball to first base, normally a routine task for a professional pitcher. This is a phenomenon known as the yips. In 2015, it was noted that Lester had not attempted a pickoff for more than one year, before creating wild throws in his latest attempts.[37] In 2018, it was reported that Lester tried to get around his problems by bouncing his throws to first base.[38]