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

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.