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 ball clubs and winning a combined three world championships with the Boston Red Sox and Chicago Cubs. The 2016 National League Championship Series Most Valuable Player is held in the highest of regards 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 always knew how to cultivate a winning culture through accountability, sacrifice, and camaraderie.   

A bona fide ace who possessed a fiery spirit, Lester was the epitome of durability and reliability. He was devoutly committed to taking the mound every fifth day as a starting pitcher while regularly fighting through pain and discomfort. Lester had started 30 or more ball games in a season 12 times. In 451 career starts, he had pitched at least seven innings in a ball game 160 times while surpassing 100 pitches on 265 occasions. In his May 2008 no hitter against the Kansas City Royals, Lester threw a career high 130 pitches.

Amid seismic changes where ball clubs began to rely heavily on the effective utilization of bullpens and the diminishment in value of the win statistic, Lester was defined by old school sensibilities in an analytically driven era. A winner of 200 major league ball games and 2,488 strikeouts, Lester is one of 59 pitchers in baseball history to have achieved at least 200 victories and 2,000 strikeouts according to Baseball-Reference’s Stathead. Presently, 34 of these pitchers are enshrined in the hallowed halls of Cooperstown with several others either currently on the ballot or will be viable candidates in the coming years.

A five-time All Star, Lester’s success has been inextricably tied to historic team achievements far more than individual accolades. He finished in the top five of the Cy Young Award voting three times across both leagues with a runner up appearance in 2016 to Max Scherzer, then of the Washington Nationals. Lester has developed a well-earned reputation for being an outstanding postseason pitcher who knew how to instill confidence in his teammates.

Over 26 postseason appearances (22 starts), Lester posted a 2.51 earned run average. In 154.0 innings, he struck out 133 batters while winning nine ball games over seven losses. However, Lester’s greatest postseason achievements had occurred during the World Series. Over six appearances (five starts), Lester posted a 1.77 earned run average while striking out 34 batters over 35.2 innings and qualifying for the win on four occasions.

It’s only natural for conversations to begin regarding Lester and the National Baseball Hall of Fame and Museum. Based solely on reputation, Lester was a starting pitcher you always wanted on the mound in a big postseason ball game. However, some will wonder if that along with a handful of statistics viewed in the appropriate context will open the gates of baseball immortality for him.   

After the December election of Jim Kaat through the Golden Days Era Committee, 18 of the 84 pitchers who are members of the National Baseball Hall of Fame and Museum are left-handed. Nine have been elected via 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). Noteworthy left-handed pitchers presently on the ballot are Mark Buehrle, Andy Pettitte, and Billy Wagner. CC Sabathia, who’s eligible for consideration beginning with the Class of 2025, will likely be the next left-handed pitcher elected in his first year of eligibility on the ballot.     

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 candidacy was greatly overshadowed by contemporaries such as Tom Glavine, Randy Johnson, Greg Maddux, Pedro Martinez, and John Smoltz. In 2019, he was eventually elected in his sixth year of eligibility on the ballot. In Lester’s case, he will confront comparisons to the likes of Zack Greinke, Clayton Kershaw, CC Sabathia, Max Scherzer, and Justin Verlander. The absence of a Cy Young Award will initially hurt Lester as it did Mussina until voters rediscovered his candidacy with greater perspective over time.      

There have been many fond recollections of Lester’s impressive career since the announcement of his retirement. One that immediately comes to mind is an October 2016 ESPN The Magazine article written by Robert Sanchez where he discusses a simple act of kindness demonstrated by Lester in May 2008 towards an 18-year-old Red Sox prospect dealing 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 your life. Most importantly, doing whatever it takes to get back onto a baseball field. The young prospect, Anthony Rizzo, never forgot Lester’s kindness as it laid the foundation for a friendship which helped them lead the Cubs to a world championship in 2016 after a drought that spanned 108 years.

Jon Lester’s retirement is bittersweet as father time is still undefeated, but we lose another tremendous ball player who played the game with integrity and a deep commitment towards building a winning culture. Not only did Lester always hold himself accountable, but he also expected teammates to do the same as well. He was a beautiful concoction of intensity, sincerity, and perseverance while playing with a profound sense of pride. He has already achieved legendary status in Boston and Chicago and one day he might be able to add the initials “HOF” at the end of his name.