Home... Transactions... Team Rosters... 40-Man Roster... 2025 Projected Rosters... Podcast
News.... Lineups.... Stats.... Draft History.... International Signings.... Scouting Log.... Forum

SoxProspects News

December 11, 2014 at 7:30 AM

Jon Lester: The rise of the $155 million man

When SoxProspects.com got its start back in 2003, left-hander Jon Lester was a tantalizing but raw talent in Single-A. The site has followed him as he rose from a projectable arm to legitimate phenom prospect to recognized ace, and now, one of the highest paid players in baseball after signing a six-year, $155 million deal with the Chicago Cubs.

Lester's time with Boston was eventful. On the field, he played key roles on two World Champions and made three All-Star teams. Off the field, he famously beat a rare form of non-Hodgkin's lymphoma. Twice the Washington native was almost traded in deals that would have brought superstar players to Boston, only to have those deals fall through.

When the 30-year old was dealt to Oakland at the trade deadline, there was some belief that the departure could be temporary. However, it was not to be. With his time with the club officially coming to a close, we at SoxProspects.com decided to make Lester the subject of our latest Player Retrospective.

2002: Draft, signing, and pro debut
Without a first-round pick due to the signing of free agent outfielder Johnny Damon, the Red Sox did not select until the 57th overall pick, when they selected Lester, a raw, tall, hard-throwing left-hander out of Bellarmine Prep in Tacoma, Washington. At Bellarmine, Lester had been named Washington's Class 4A Co-Player of the Year, an award he shared with another future playoff hero, Travis Ishikawa. Perfect Game rated Lester the #11 high school prospect in the draft, noting that the "big, athletic lefty" was also considered a prospect as a first baseman. Additionally, Lester was a standout basketball player at Bellarmine. 

A $1 million bonus convinced Lester to forgo his commitment to join star shortstop Dustin Pedroia as a member of the Arizona State Sun Devils. The bonus was the highest given that season to any player taken after the first round. With the signing deadline later on the calendar in those days, Lester was not brought into the fold until August 13. He was assigned to the Red Sox Gulf Coast League affiliate, and took the mound for his first professional start on August 23. It was an inauspicious opening. The 6-foot-6 lefty retired only two of the nine batters he faced, giving up six runs (five of which were unearned) on five hits and a walk. Despite his lack of pro experience, Baseball America rated him the #8 prospect in the organization, citing his "projectable body and easy arm action."

2003-2004: Early promise, early inconsistency
With a full offseason to prepare and the contract negotiation stage behind him, Lester entered his first full pro season. Despite his being only 19 on opening day, the Red Sox and new general manager Theo Epstein challenged the lefty with a placement in Augusta of the Low A South Atlantic League. Unsurprisingly, it was a struggle at times. Starting 21 of his 24 appearances, Lester was able to reach 106 innings. While his 97-mph fastball was not yet translating into missed bats—he struck out only 71 in that first season—a solid 3.65 ERA and 1.38 WHIP against advanced competition showed off some of his potential. Following his solid debut, Baseball America ranked him the 15th-best prospect in the Florida State League.

Lester also gained the attention of the Texas Rangers. Had the MLBPA not intervened, Lester would have found himself going south, along with Manny Ramirez, in exchange for star shortstop Alex Rodriguez, while another deal would have shipped Nomar Garciaparra to Chicago for Magglio Ordonez. The deal had included a reworking of Rodriguez's contract that was subject to players association approval. Without that consent, the deal fell through. Rodriguez was, of course, dealt instead to the New York Yankees, while Lester, Ramirez, and Garciaparra remained members of the Red Sox.

Expectations were high entering 2004. Lester did not find himself on Baseball America's Top 100, but he went into the season with the top ranking on SoxProspects.com. He would find himself assigned to Sarasota, then Boston's affiliate in the High A Florida State League. Much like 2003, it was a mixed result, filled with both progress but reasons to be cautious. After striking out only 6.0 batters per nine innings in 2003, that mark jumped to an excellent 9.7. Perhaps most encouragingly, the improved strikeout rate did not come at the expense of his control, as his walks remained an identical 3.7 per nine innings. Unfortunately. Lester's ERA did not follow, rising to 4.28. He fell from first to sixth on the SoxProspects.com rankings, though much of that was due to strong seasons from several prospects during the 2004 season. All five players who jumped ahead of him went on to play in the major leagues, with four becoming All-Stars: Hanley RamirezBrandon Moss, Dustin Pedroia, and Jonathan Papelbon. Only Abe Alvarez, who experienced a meteoric rise through the system that year, did not see major league success. 

2005: A hot prospect emerges
Lester continued his steady climb up the ladder, getting the assignment to Double-A Portland to begin his age-21 campaign. It was there at Hadlock Field that Lester gained the baseball world's attention as a prospect to keep its eyes on. In 26 starts, he reached 148 1/3 innings, striking out an Eastern League-leading 163 while walking 57. He gave up only 114 hits, a paltry 6.9 per nine innings, on his way to a 2.61 ERA. The awards and recognition followed. Lester was named the Eastern League Pitcher of the Year, while the Red Sox tabbed him as their 2005 Minor League Pitcher of the Year. Baseball America noticed as well, as the previously unranked Lester made the publication's Top 100 prospect list at #22 overall. SoxProspects.com had him second in the system behind only Papelbon, whose major league success gave him the edge.

2006: Exciting debut, a more important fight
Expectations were soaring entering 2006, and Lester's performance continued to feed them. In 11 starts at Triple-A Pawtucket, the 22-year-old delivered a 2.70 ERA in 46 2/3 innings. He added 43 strikeouts, and the only blemish was his 25 walks, a higher rate than in previous seasons. The strong performance and the graduation of Papelbon elevated Lester back to the SoxProspects.com top ranking.

With the tall lefty pitching well and the major league rotation in turmoil, the Red Sox called Lester up to make his major league debut on June 10 at Fenway against the Texas Rangers. He gave up three runs on five hits in 4 1/3 innings, taking a no-decision in a game the team would eventually lose. He then reeled off seven straight strong starts, pitching at least five innings and allowing two or fewer runs in each. Through eight starts, Lester stood at 5-0 with a 2.38 ERA. While the league made some adjustments in his next seven starts, on August 23, he stood at 7-2 with a 4.76 ERA. 

Amid the excitement of his early success, baseball quickly turned into a secondary consideration. A routine test following a minor traffic collision uncovered an abnormality, which additional testing revealed as a rare form of anaplastic large cell (non-Hodgkin's) lymphoma. Lester was placed on the disabled list and began a treatment regimen that included chemotherapy.

2007: Conquering cancer, then the World Series
After a winter of treatment, Lester arrived to spring training cancer free. He was not yet, understandably, back to playing shape. The Red Sox worked their phenom back slowly, assigning him to Low A Greenville out of spring training to begin a long rebuilding process. He retook the mound on April 5, firing four shutout innings. Across three starts with Greenville and one at Portland, he allowed only four runs in 19 innings, striking out 19 and walking six. He joined Pawtucket in late April, where his only setback was unrelated to his cancer scare, leaving his May 2 start with forearm soreness. The issue proved to be minor, and Lester did not miss a start. In 14 starts with the PawSox, he compiled a 3.89 ERA, striking out 51 and walking 31 in 71 2/3 innings. While the statistics may not have been eye-popping, the team felt he was back to full strength (as did Lester, who SoxProspects.com Executive Editor Chris Hatfield remembers being quite clearly irked at still being in Pawtucket during interviews at the time), and he was recalled to the majors on July 23.

With the Red Sox in the thick of the pennant race, Lester arrived at Jacobs Field to take on the Central Division-leading Cleveland Indians. Before he even took the mound, an outburst in the top of the first staked him to a 4-0 lead that would be more than enough. Lester gave up two runs on five hits in six innings, earning his first win in 11 months. He would go on to win his next three decisions, finishing with a 4-0 record and 4.57 ERA in 12 outings, a big part of Boston's division-winning drive.

After getting his feet wet with a pair of relief appearances in the League Championship Series, the rookie was called on to start the fourth game of the World Series in Coors Field. Only nine months after his cancer was declared in remission, Lester tossed 5 2/3 scoreless innings to earn the win in the clinching game of the Red Sox's second World Series championship in four years.

2008-2011: From trade chip to ace
Coming off his historic performance, Lester faced a different sort of uncertainty in the offseason, as Lester again found himself embroiled in trade rumors. The Minnesota Twins were looking to deal two-time Cy Young Award winner Johan Santana. The Red Sox were considered a front-runner, and rumors abounded that Lester was considered a likely centerpiece. However, given the reportedly exorbitant demands by the Twins, the Red Sox pulled out of the Santana sweepstakes.

It turned out to be the correct decision. After an up-and-down April, Lester began to turn the corner as the weather warmed, and on May 19 he would deliver one of the defining moments of his career: a no-hitter against the Kansas City Royals at Fenway Park. He blew past the 200 inning mark that season, finishing with a 3.21 ERA. After another strong season in 2009 with over 200 innings, 225 strikeouts, and a 3.41 ERA, Lester followed with a 2010 that put him among the best in the game. He won a career-best 19 games, striking out 225 in 208 innings and finishing fourth in the Cy Young Award voting. In 2011, Lester was again a key contributor, with a 3.47 ERA in 191 2/3 innings. However, he was a key part of the team's frustrating collapse at the end of the season, going 1-3 with a 5.40 ERA in six starts.

2012-2013: Worst to first
Like everything else the Red Sox touched in 2012, Lester's season was inexplicably poor. Under the leadership of Bobby Valentine and a pair of pitching coaches in the embattled Bob McClure and Valentine cohort Randy Niemann, Lester turned in what was by far the worst campaign of his career. His 9-14 record marked the only time he has finished below .500, and his 4.82 ERA was his highest at any level where he had made more than one start.

While the team experienced a resurgence under John Farrell to kick off 2013, Lester continued to labor, carrying a 4.58 ERA into the All-Star break. Fortunately for both Lester and the Red Sox, he got back on track and did not miss another beat. Lester delivered a 2.57 ERA in 13 second-half starts, striking out 74 and walking 22 in 87 2/3 innings, leading the Red Sox to the Eastern Division crown. That was simply a warm-up for a sublime postseason. Across five starts, Lester allowed only six runs in 34 2/3 innings, striking out 29 and walking 8. He was twice the winning pitcher against the Cardinals in the World Series. In 15 1/3 innings, he held the National League Champions to just one run.

2014: The end of an era
Lester's momentum from 2013 continued into the following season. Through 21 starts he had a 2.52 ERA, 149 strikeouts in 143 innings, and the lowest walk rate of his career. However, that momentum did not carry to the rest of the team. In late July, the Red Sox were mired in last place, and there had been little in the way in talks on a possible contract extension with the pending free agent. At the deadline, Lester was dealt, along with outfielder Jonny Gomes to the Oakland Athletics for outfielder Yoenis Cespedes and a draft pick.

Hopes of a reunion were quashed when Lester signed a six-year deal with the Chicago Cubs, reuniting him with Epstein. At the time of the July trade, he was the longest-tenured player in the organization, having signed five months before designated hitter David Ortiz. He ranks fourth on the all-time Red Sox leaderboard in strikeouts with 1386 and ninth in wins  with 110.

Photo Credit: Jon Lester by Kelly O'Connor