In an offseason of on and off-the field departures for the Chicago Cubs, Jon Lester ends a phenomenal six- year run with Chicago as he signs a one-year deal with a mutual option with the Washington Nationals. Lester struggled like the rest of the Cubs in 2020, but his career with the team is nothing other than exactly what the organization and the fans wanted.
Lester came to Chicago with huge expectations and an even bigger contract. His six-year $155 million was the first big free agent signed by the Theo Epstein regime. He joined a budding starting rotation with Jake Arrieta and Kyle Hendricks and a young core led by rookies Kris Bryant, Addison Russell, and veteran Anthony Rizzo. While expectations on the new look Cubs were optimistic, the Cubs still stunned MLB with a 97-win season and the organizations first playoff appearance in six seasons.
While Lester was good in his first Cubs season, it was Jake Arrieta who shined brightest and won the NL Cy Young. Lester continued to play second fiddle to Arrieta in the postseason as his 2015 postseason ERA of 4.54 halted the Cubs miracle postseason at the hands of Daniel Murphy and the New York Mets.
In 2016, Lester rebounded from a middling 2015 to finish second in NL Cy Young voting. His 19-5 record and 2.44 ERA across 202.2 innings were some of the best marks of career. The veteran led the Cubs to MLB’s best record at 103- 58.
In the postseason Lester dominated to the tune of a 2.30 ERA across 35.2 innings, winning the co- NLCS MVP with Javier Baez. In the Cubs first World Series appearance since 1945, Lester was integral in the teams improbable 3-1 comeback. Only two seasons into his contract, Lester was able to help the Cubs break their franchise curse and win the 2016 World Series.
After 2016, Lester’s production dipped noticeably. From 2008- 2016, Lester’s career averages included a 15-9 record with a 3.34 ERA across 207 innings. From 2017- 2109, the veteran southpaw posted seasonal averages of a 15-8 record with a 4.03 ERA across 178 innings. While his production wasn’t terrible, the veteran was trending in the wrong direction along with the rest of the roster.
Jon Lester 2008- 2016
Jon Lester 2017- 2019
With a roster on the decline to mirror his own play, Lester was one of many Cubs to struggle in the COVID-19 shortened season. Lester’s 5.16 ERA across 61.0 innings is far from how the Cubs or Lester imagined his final season with the organization would go, but that’s baseball.
Lester’s time in Chicago will be remembered for more than his play on the field as he’s endeared himself to Chicago and Cubs fans through his many charitable donations and events. Lester has raised money with his organization NVRQT (Never Quit) for cancer research, recently hosting a country-themed event to raise money during the COVID-19 pandemic. Even on his way out of the organization Lester gave Cubs fans the only gift they wanted other than a World Series championship by ordering over $25 thousand in beer.
As the veteran begins a new chapter with the Nationals, there are no hurt feelings or malice from the Cubs organization or fans, only appreciation for the greatness he shared with them. Lester’s time in blue pinstripes may be over, but he will always be remembered in Chicago as a World Series champion, All- Star, and overall legend.