Jon Lester’s Top 5 Cubs’ Moments

Jon Lester has officially called it a career after 16 major-league seasons. Although he spent more time in a Red Sox uniform, many will argue the most influential stretch of his career came on the tail-end with the Chicago Cubs. In his 6 seasons in Chicago, Lester posted a 77-44 record and 3.64 ERA, while earning a second-place Cy Young finish and leading the way to the Cub’s first World Series in 108 years. He is easily the most successful free-agent addition the team has ever brought in and left many notable moments in pinstripes for fans and teammates alike to remember him by.

Top Moments in a Cubs’ Uniform

1. World Series Game 7

How could this not be #1 on the list? In the 2016 World Series Jon Lester went 1-1 with a 3.62 ERA, but his Game 7 appearance is most notable. After winning Game 5 as the starter, Lester took the hill in relief of Kyle Hendricks on just two days rest. Despite allowing two runs to score on a wild pitch in his first inning, the lefty settled in and struck out 4 Cleveland hitters over 3 innings. This allowed for then-manager, Joe Maddon, to hand the ball off to Aroldis Chapman in the 8th inning with a 3-run lead. As all of Cubs’ faithful remembers, this ended up being critical due to the near-heartbreaking disaster Chapman created.

Even though he did not get the win, Lester’s impact was undeniable. Having the confidence to pitch on short rest in the biggest game in MLB history is something few starting pitchers would ever have the confidence or ability to do. A true definition of the term “Ace”.

2. 2016 NLCS

Game 7 will always be the most memorable postseason victory for Lester and Co, but they may have never had the chance to be there if not for his incredible performance in the NLCS. Tasked with starting Game 1, Lester began the series with just four hits and one run allowed across 6 innings. In spite of earning a no-decision due to the Dodgers scoring late off Aroldis Chapman (again), the Cubs won and Lester set the tone for the rest of the series. When he took the bump again in Game 5, the veteran once again cruised through the Dodger lineup throwing seven innings of one-run baseball while adding six strikeouts en route to another Cubs win. All in all, Lester posted a 1.38 ERA across 13 IP and earned Co-MVP honors with Javy Baez.

3. First Career Homer

When the Cubs signed Lester in 2015, he had only pitched in the American League. Due to this, at-bats were hard to come by and it’s understandable that taking an approach at the plate was not near the top of his priority list. In 36 career at-bats before joining Chicago he had 0 hits. It took some time for Lester to get comfortable with a bat in his hand, but on August 1, 2017, he finally did the unthinkable and hit his first career home run. The opposite-field blast sure did get the monkey off his back at the plate as he knotched a home run in each of the next three seasons as well.

4. Walk-Off Bunt

Home runs may be the easiest way for a pitcher to get on an offensive highlight reel, but Lester found a more unique way the season before. On July 31, 2016, Lester shockingly was called on to pinch-hit in the bottom of the 12th inning of a 6-6 game with the Seattle Mariners. The southpaw laid down the perfect bunt as Jason Heyward barrelled towards home and slid in under the tag for the 7-6 victory. The Cubs core secured many memorable and fun walk-off wins at Wrigley from 2015-2019, this may take the cake as the strangest and least likely of the bunch.

5. Pick-off of Tommy Pham

Lester’s career was filled with illustrious accolades accomplished by only a few of his counterparts. Regarded for retiring with the 3rd-most wins by an active pitcher (200) and 5th-most strikeouts (2,488), Lester was possibly even more well known to be among the worst in the league in one particular category…pick-offs. Left-handed pitchers often have a major advantage to control the runners on the basepaths and dominate the pace of the game. Jon however suffered from the Yips, a sudden unexplained loss of the ability to do simple motor skills. Whether the cause was physical or mental, the yips made it nearly impossible for Lester to execute a pick-off move to first base.

Many people called out Lester for this inability and even went as far as to question whether it could cost the Cubs a playoff series. Lester finally decided to silence his critics on June 3, 2017. The Fox announcing crew repeatedly poked fun at Lester and guaranteed he would let Pham go to second. To everyone’s surprise, Lester indeed did throw over and Pham was ruled out. Whether it be due to breaking a curse, or simply the joy of making the Cardinals look dumb, this moment finds its way onto the list of Lester’s best moments.

Today is Jon Lester's birthday,
the perfect day to air the Cardinals' broadcast
of the time Tommy Pham
took this giant lead off Lester at Wrigley
knowing Lester does not like to throw to first.
Perfect announcing by Tim McCarver, I believe. pic.twitter.com/BRbPLrGIUH

— tony pierce (@busblog) January 8, 2022

Honorable Mention: Charity Work and “Lester Lites”

Aside from all of his accomplishments on the field, Jon Lester made it a priority to give back to the community and show his appreciation for the city of Chicago. Lester, a non-Hodgkin lymphoma survivor, was well-known for his charity work outside of Wrigley Field. Whether it be putting on events with his NVRQT foundation or donating meals to frontline workers during the Coronavirus pandemic, Lester was always focused on giving back.

On the lighter side of connecting with the community, when it was made official that he would not return to the Cubs after the 2020 season Lester made a very unique donation to the Cubs fans who supported him for so many years.

Thanks for coming out this weekend y’all! Yesterday we added 1,372 ⁦@MillerLites⁩ to my tab, bringing our grand total to 4,838. Shout out to all the bars, their staff, and those cheers-ing from afar! Whether this is goodbye or see you next year, I love you Chicago! #JonsTab pic.twitter.com/OTEIO2gOjc

— Jon Lester (@JLester34) November 2, 2020

As a parting gift to fans, Lester provided a “first-round” for all fans at the bars surrounding Wrigley Field, as well as some of the Old Town establishments on Division St. After nearly 5,000 free beers were handed out, Lester found one more way to make fans appreciate him. I fully expect the favor to one day soon be returned to the Cub’s legend as he has checked off every box for having his #34 jersey immortalized at Wrigley Field forever flying from the foul pole.