Jon Lester’s 16-year career perfectly blended intensity and winning with leadership
Left-handed starting pitcher Jon Lester recently announced his retirement after a 16-year career that spanned five major league baseball clubs and won three combined world championships with the Boston Red Sox and Chicago Cubs. The 2016 National League Championship Series Most Valuable Player is held in high regard by former teammates for his competitive nature, generosity and exemplary leadership. Unafraid to share his opinions and speak freely on a wide range of topics, Lester has always cultivated a winning culture through responsibility, sacrifice and camaraderie.
A bonafide ace who possessed a fiery spirit, Lester was the epitome of durability and reliability. He fervently committed to taking the mound every five days as a starting pitcher while regularly battling pain and discomfort. Lester had started 30 or more games in a season 12 times. In 451 career starts, he had pitched at least seven innings in a ballgame 160 times while going over 100 pitches 265 times. In his tie against the Kansas City Royals in May 2008, Lester threw a career-high 130 pitches.
Amid the seismic changes where ball clubs began to rely heavily on the effective use of relievers and the dwindling value of the win stat, Lester was defined by old-school sensibilities at a time. analysis-oriented. The winner of 200 major league baseball games and 2,488 strikeouts, Lester is one of only 59 pitchers in baseball history to have at least 200 wins and 2,000 strikeouts according to Baseball’s Stathead- Reference. Currently, 34 of those pitchers are registered in the hallowed halls of Cooperstown and several more are currently on the ballot or will be viable candidates in the years to come.
A five-time All Star, Lester’s success is inextricably tied to the team’s historic accomplishments far more than individual accolades. He finished in the top five in the Cy Young Award voting three times in both leagues with a 2016 appearance against then-Washington Nationals Max Scherzer. Lester developed a well-deserved reputation as an outstanding playoff pitcher who instilled confidence in his teammates.
Over 26 playoff appearances (22 starts), Lester posted a 2.51 ERA. In 154.0 innings, he struck out 133 while winning nine ball games in seven losses. However, Lester’s greatest playoff accomplishments came during the World Series. In six appearances (five starts), Lester posted a 1.77 ERA while striking out 34 batters in 35.2 innings and going for the win four times.
It’s only natural for conversations to arise regarding Lester and the National Baseball Hall of Fame and Museum. Based on reputation alone, Lester was a starting pitcher you always wanted on the mound in a big playoff ball game. However, some will wonder if that, coupled with a handful of stats seen in the proper context, will open the door to baseball immortality for him.
After the December election of Jim Kaat through the Golden Days Era Committee, 18 of the 84 pitching members of the National Baseball Hall of Fame and Museum are left-handed. Nine were elected through the Baseball Writers’ Association of America (BBWAA). Only five were elected in their first year of eligibility: Sandy Koufax (1972), Warren Spahn (1973), Steve Carlton (1994), Tom Glavine (2014) and Randy Johnson (2015). Notable left-handed pitchers currently on the ballot are Mark Buehrle, Andy Pettitte and Billy Wagner. CC Sabathia, who is eligible as of the Class of 2025, will likely be the next left-handed pitcher elected in his first year of ballot eligibility.
Lester could possibly have a similar experience to Mike Mussina when it comes to his time on the Hall of Fame ballot. Mussina’s outstanding career and Hall of Fame bid were largely overshadowed by contemporaries such as Tom Glavine, Randy Johnson, Greg Maddux, Pedro Martinez and John Smoltz. In 2019, he was finally elected in his sixth year of being eligible to vote. In Lester’s case, he’ll face comparisons to Zack Greinke, Clayton Kershaw, CC Sabathia, Max Scherzer and Justin Verlander. The lack of a Cy Young award will initially hurt Lester as it did Mussina until voters rediscover his candidacy with greater perspective over time.
There have been many fond memories of Lester’s impressive career since his retirement announcement. The one that immediately comes to mind is the one from October 2016 ESPN The Magazine item writing by Robert Sanchez where he discusses a simple act of kindness shown by Lester in May 2008 to an 18-year-old Red Sox prospect struggling with Hodgkin’s lymphoma. A survivor of anaplastic large cell lymphoma, Lester mentored the young prospect on the importance of fighting, constantly moving forward and living life. More importantly, do whatever it takes to get back on a baseball field. The young prospect, Anthony Rizo, never forgot Lester’s kindness as it laid the foundation for a friendship that helped lead the Cubs to a world championship in 2016 after a drought that lasted 108 years.
Jon Lester’s retirement is bittersweet as the time of the fathers is still undefeated, but we are losing another tremendous baseball player who played the game with integrity and a deep commitment to building a winning culture. Not only did Lester always hold himself accountable, but he also expected his teammates to do the same. He was a beautiful concoction of intensity, sincerity and perseverance while playing with a deep sense of pride. He has already achieved legendary status in Boston and Chicago and may one day add the initials “HOF” to the end of his name.