Chicago Cubs: Top 5 Jon Lester moments in a Cubs uniform

Chicago Cubs: First career home run

With all due respect to the multiple “ball stuck in the glove” flips to Anthony Rizzo early in his Cubs career, this is the lighthearted moment that makes the list.

After spending eight seasons in the American League, Lester was far from adept at handling the bat when he came to Chicago. Indeed, he mustered just four hits in 71 plate appearances in 2015.

But Big Jon has shown subtle improvements at the dish over the past four years, including a memorable walk-off bunt against the Seattle Mariners in 2016. And in an Aug. 1 matchup against the Arizona Diamondbacks in 2017, he cranked his first big-league homer.

From the crowd reactions to the bullpen dancing and the clear shock expressed by Len Kasper and Jim Deshaies, this was clearly a moment to remember.

Chicago Cubs: Wild Card brilliance against the Rockies

The Cubs’ season may have come to a disappointing end in the NL Wild Card game, but Lester was absolutely dominant on the mound – doing everything in his power to propel his club to the NLDS.

After giving up a run in the first inning, Lester settled in to scatter four hits across six innings of work, striking out nine and keeping Rockies hitters off balance all game long:

It was the kind of performance that has come to define Lester as a big-game, down-and-dirty pitcher the Cubs want to send to the hill with their season on the line.

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Perhaps most notably, however, Lester showed strong veteran leadership in his postgame comments, where he noted that the loss may serve as a wake-up call that this young Cubs nucleus cannot simply rely on talent to succeed.

Decimating the Dodgers in Game 5 of the NLCS

With the 2016 NLCS tied at two games apiece, the Cubs sent Lester to the hill against Dodgers right-hander Kenta Maeda.

After struggling to mount any offense in Game 2 and Game 3, Chicago had finally erupted for ten runs in a crucial Game 4 win.

But after scoring a run in the top of the first, the bats fell silent as Los Angeles eventually tied the game in the fourth inning.

No matter. Lester stymied the Dodgers in the middle innings before Addison Russell‘s two-run homer off of Joe Blanton gave the Cubs the lead for good.

The big left-hander allowed just one run on five hits in seven innings of work in a tremendous performance where the intensity was palpable from the first pitch on.

Chicago Cubs: Keeping World Series hopes alive

After losing consecutive games at Wrigley Field in the 2016 World Series, the onus was on Lester to keep Chicago’s championship dreams alive in Game 5 against the Cleveland Indians.

He struck out the side in order in the top of the first inning, but Jose Ramirez hit a two-out homer to give Cleveland the lead in the top of the second. But in yet another show of will and determination, Lester was unfazed.

He retired the side in each of his next three innings, allowing enough time for the Cubs to squeak out three runs off of Indians starter Trevor Bauer in the fourth inning and subsequently preserving the lead.

Despite giving up a run in the top of the sixth, Lester had scattered four hits across six innings and kept the Cubs in front, doing his job marvelously before a historic performance by Cubs closer Aroldis Chapman sent series back to Ohio.

Chicago Cubs: The relief appearance in Game 7

Imagine entering Game 7 of the World Series on the road on just two days of rest and being asked to deliver crucial outs in the middle innings. Daunting, right?

Not to Jon Lester.

Things looked shaky for the big lefty initially. Cubs manager Joe Maddon had pulled starter Kyle Hendricks after Carlos Santana walked with two outs in the top of the fifth.

Lester’s first batter was Jason Kipnis, who rolled a dribbler down the third base line and forced an errant throw that sent Santana to third and Kipnis to second. One crazy wild pitch later, and the Indians had trimmed what was a 5-1 deficit to just two.

But as he has done so many times, Lester collected himself. He retired Francisco Lindor to end the inning, then threw 2 2/3 scoreless innings in arguably his gutsiest performance ever.

The rest, as they say, is history.