Looking Back at Chicago Cubs Starting Pitcher Who Was Postseason Hero

A former Chicago Cubs starting pitcher was recognized recently for his postseason heroics.

Sep 26, 2020; Chicago, Illinois, USA; Chicago Cubs starting pitcher Jon Lester (34) throws a pitch against the Chicago White Sox during the first inning at Guaranteed Rate Field. / Mike Dinovo-Imagn Images

It has been a while since the Chicago Cubs were playing baseball deep into October.

2024 was the fourth straight year that they missed the postseason. 2017 is the last time that they won a playoff series, as they took home the World Series in 2016, ending their insanely long drought.

There were a lot of key contributors to that team making a run to the championship. The biggest hero of that group was starting pitcher Jon Lester.

A five-time All-Star and three-time champion, the lefty had some of the best seasons of his career with the Cubs. But what he did during that postseason run was truly memorable.

The bright lights and big stage of the MLB postseason did not phase Lester. He would regularly rise to the occasion and he did the same for Chicago in 2016.

In six appearances, with five starts, he threw 35.2 innings, allowing 27 hits with 30 strikeouts and only six walks. He had a 2.02 ERA and was named NLCS MVP.

“The lefty did no wrong in his first three starts of the playoffs, logging eight scoreless innings in Game 1 of the NLDS against the San Francisco Giants and then racking up 13 innings of two-run ball against the Los Angeles Dodgers in the NLCS. The Cubs won all three games.

Though Lester lost Game 1 of the World Series, he was the winning pitcher when the Cubs started their comeback from a 3-1 deficit versus Cleveland in Game 5. And when he handed the ball to Aroldis Chapman in Game 7, the Cubs had a 95 percent chance of winning,” wrote Zachary D. Rymer of Bleacher Report in a piece highlighting the best postseason performances of the last decade.

Of course, nothing is as easy for Chicago fans as a 95 percent chance of winning would imply. Chapman would blow the game, as they went into extra innings.

There, another hero emerged as Ben Zobrist hit a double to put the Cubs ahead once and for all.

Lester is one of the most underrated and underappreciated pitchers in recent history. His postseason resume is stellar, making 26 appearances (22 starts) and going 9-7 with a 2.51 ERA.

Across 154 innings he struck out 133 batters and had a WHIP of 1.019. Virtually every time he took the mound he gave his team a chance to win the ball game, which is all you can ask for against that level of competition.

Along with ending the championship drought for Chicago, he was part of the Boston Red Sox team that broke the Curse of the Bambino. If you are working for a team that hasn’t found playoff success in a long time, you need to get on the phone and bring Lester into the fold in some capacity.