High school career

Lester attended Bellarmine Preparatory School in Tacoma, Washington. Playing for the school's baseball team, Lester was a three-time MVP and three-time All-Area selection. In addition, he was named Gatorade State Player of the Year for Washington in 2000.

Professional career

Boston Red Sox

The Red Sox drafted Lester in the second round (No. 57 overall) 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. 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.

2006

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. A few days later, doctors at Massachusetts General Hospital confirmed that Lester had a treatable form of anaplastic large cell lymphoma. Lester underwent off-season chemotherapy treatments at Seattle's Fred Hutchinson Cancer Research Center, named after Fred Hutchinson, who died of cancer at age 45 in 1964. In December 2006, ESPN.com reported that Lester's latest CT Scan showed no signs of the disease, which appeared to be in remission.

2007

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. In June, Lester was removed from the disabled list, and sent to Pawtucket for further rehab outings.

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. 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.

2008

On May 19, 2008, Lester threw a no-hitter in a 7-0 win against the Kansas City Royals. 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.

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.

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

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

2009

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

The season started poorly, with him allowing 11 runs and getting losses in his first two starts 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 61⁄₃ 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 was chosen to start game one of the ALDS, and also of the World Series. He had become Boston's ace.

2010

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 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.

2011

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.

2012

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.

2013

On May 10, 2013, Lester threw a complete game one-hitter, with 0 walks, against the Toronto Blue Jays, facing only 28 batters. Cy Young still remains as the last pitcher to throw a perfect game with the Red Sox, back in 1904.

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 Anibal Sanchez. 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 to 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.

2014

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.

Oakland Athletics

On July 31, 2014, Lester and Jonny Gomes were traded to the Oakland Athletics for Yoenis Cespedes and a competitive round 2015 draft pick. The move reunited Lester with former teammates Jed Lowrie, Coco Crisp, Brandon Moss and Josh Reddick. He won his debut start against the Kansas City Royals on August 2. 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 had a 16-11 record with a 2.46 ERA and finished 4th in the AL Cy Young voting.

Chicago Cubs

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.

2015

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. 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.

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. 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 a 11-13 record, logging 205 innings pitched with an ERA of 3.34 in his first year with the Chicago Cubs

On Oct. 9, 2015 he was the losing pitcher in Game One of the NLDS vs. the Cardinals. On Oct. 17, 2015 he took another loss in Game One of the NLCS vs. the New York Mets.

Personal life

In 2015, Forbes estimated that Lester's annual income was $34 million.

Lester grew up in Puyallup, Washington and attended All Saints School. He later attended Bellarmine Preparatory School where he was a three-time MVP and three-time All-Area selection. On January 9, 2009, Lester married Farrah Stone Johnson, whom he met in 2007, while making rehab starts in single-A Greenville. They have 2 sons together.

In March 2011, Jon Lester partnered with Charity Wines to release his own wine label under the Longball Cellars brand. Proceeds from sales of his CabernAce cabernet support the Hutchinson Cancer Research Center, the place where Lester himself was treated, to aid the development of targeted immunotherapies. Funds raised from this initiative will help researchers maximize the body’s own ability to strike out and eliminate disease so lymphoma patients can extend their life. He is partnering with former teammate Clay Buchholz who is also releasing a Charity Wine, called ChardonClay, to raise money for the Jimmy Fund.

Lester and his wife Farrah established NVRQT, short for "Never Quit", in 2011 to support children with cancer and researchers working towards a cure. Lester has written guest columns about his cause on Boston.com and CNN.com.

In his free time, Lester is an avid hunter and a wine aficionado. During the 2015 offseason, in an attempt to woo him, the Chicago Cubs sent Lester fine wines and camouflage Cubs shirts.

[ Source: Wikipedia ]