Cubs: Remembering Jon Lester’s unexpected first career home run

On Tuesday morning, we learned Jon Lester, the greatest free agent acquisition in Chicago Cubs history, would be retiring after 16 major league seasons just a couple days after his 38th birthday.

Lester will finish his career with an even 200 wins, a 3.66 ERA, five All-Star appearances and three World Series rings. He is known for his time on the mound, dominating batters with the power in his left arm. But you’d better put some respect on this man’s bat too.

August 1, 2017. In the middle of a season where the Cubs were looking to repeat as World Series champions, Lester was in the middle of a bet with longtime teammate and friend John Lackey. The bet was to see who would hit their first career home run first. Lester won the bet on this night with one swing of the bat.

Chicago Cubs: Jon Lester: pitcher, leader, slugger

The Cubs were up 6-1 on the lowly Arizona Diamondbacks. With one on and two out, Lester stepped up to the plate with nothing to lose. He connected on a 2-2 cutter and drove it to deep left-center field, clearing the wall and landing into a sea of bleacher bums. You want to talk about electric Wrigley moments? This one is right up there.

Lester will be remembered for his durability, his leadership, his “never quit” attitude, and, without a doubt, his bat. He ended his career with four home runs, three of those coming with the Cubs.

With a league-wide designated hitter warming up in the on-deck circle, it is likely pitchers like him will not be able to show out with their bats any longer. So if his arm isn’t enough to sway you to put him in the Hall of Fame, you’re wrong. But his bat will put him over the top.