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.