Skip to main content
SM Edge
Scout

Ask Scout

AI sports analysis

LIVE
Teams
Bears logoBearsBulls logoBullsCubs logoCubsBlackhawks logoBlackhawksWhite Sox logoWhite Sox
SM ✶ EDGE Features
Fan ChatLIVE
Game Center
War Room
Team Stats
Vision Theater
Hands-Free Audio
Podcasts
A+
GM Report Cards
SM Edge
SM Edge
Scout

Ask Scout

AI sports analysis

LIVE
Teams
Bears logoBearsBulls logoBullsCubs logoCubsBlackhawks logoBlackhawksWhite Sox logoWhite Sox
SM ✶ EDGE Features
Fan ChatLIVE
Game Center
War Room
Team Stats
Vision Theater
Hands-Free Audio
Podcasts
A+
GM Report Cards
Sports Mockery

The future of Chicago sports. AI-powered, fan-driven, unmatched.

Platform

Scout AIWar RoomData CosmosFan Hub

Teams

Chicago BearsChicago BullsChicago CubsChicago White SoxChicago Blackhawks

Company

SM+ PremiumAboutContactPrivacy PolicyTerms of ServiceGovernance
© 2026 Sports Mockery. All rights reserved.Chicago's #1 AI Sports Platform
HomeScout AIScout AIGMFan ChatProfile
Jon Lester's Top 5 Cubs' Moments
Jon Lester's Top 5 Cubs' Moments

Jon Lester's Top 5 Cubs' Moments

M
Michael Jacobucci
·
January 13, 2022·5 min read·561
0:00
0:00
Scout AIScout Recap
Ask Scout more

Frequently Asked Questions

What did Jon Lester do in Game 7 of the 2016 World Series?+
Lester came out of the bullpen on just two days rest to relieve Kyle Hendricks, striking out 4 Cleveland hitters over 3 innings despite allowing two runs on a wild pitch. His performance gave Joe Maddon a 3-run lead to hand off to Aroldis Chapman in the 8th inning. It remains one of the most clutch relief appearances in Cubs history.
When did Jon Lester hit his first career home run?+
Lester hit his first career home run on August 1, 2017, an opposite-field blast that ended a 0-for-36 hitless streak dating back before he joined the Cubs. He then homered in each of the next three seasons as well.
How did Jon Lester get a walk-off as a pitcher for the Cubs?+
On July 31, 2016, Lester was called on to pinch-hit in the bottom of the 12th inning of a 6-6 tie against the Seattle Mariners and laid down a perfect bunt, allowing Jason Heyward to slide in under the tag for a 7-6 Cubs victory. It stands out as one of the strangest walk-off wins from the Cubs' memorable 2015-2019 run at Wrigley.
What were Jon Lester's stats and awards during the 2016 NLCS?+
Lester posted a 1.38 ERA across 13 innings in the 2016 NLCS against the Dodgers, earning Co-MVP honors alongside Javy Baez. He started Games 1 and 5, with his Game 5 outing going seven innings of one-run ball with six strikeouts.
Why was Jon Lester famous for his yips and what happened with Tommy Pham?+
Lester suffered from the yips, an unexplained loss of the ability to execute a pickoff throw to first base, which drew heavy criticism and speculation about whether it could cost the Cubs in the playoffs. On June 3, 2017, he silenced his critics by picking off Tommy Pham of the Cardinals, even as the Fox broadcast crew repeatedly joked on-air that he would never throw over.
Share:
M

Michael Jacobucci

View All Posts
Scout · Cubs room

Join the Chat

Chicago fans are talking about this in Fan Chat.

Jon Lester's Top 5 Cubs' Moments
SM★EDGE Features
Fan ChatMembers
Skip the comments and argue it out live.
War Room
Play GM — simulate trades, run mock drafts, and compete against other SM users.
Team Stats
The numbers that explain the wins... and the excuses.
Vision Theater
All videos, no digging. Just press play.
Hands-Free Audio
Sit back, choose a voice, and press play.
Podcasts
Raw takes, smart analysis, and nonstop debate.
GM Report Cards
Transparent, data-backed grades on every Chicago ownership group.