When Jon Lester came to the Cubs, he was a terrible hitter. No, seriously. He had gone 0-for-36 in his American League career, and that carried over to his first year with the Cubs in 2015. Lester went
0-for-30 in his first 16 Cubs starts, finally breaking that 0-fer with a single off his friend and future Cubs teammate, John Lackey, July 6, 2015, a game the Cubs eventually lost 6-0.
The hit was literally off Lackey:
After that, though, Lester slowly became a better hitter. Not a GOOD hitter, but enough so that you could call him “a decent hitter for a pitcher.” He had three more hits and six successful sacrifice bunts the rest of 2015 and even drew three walks.
In his first 21 starts of 2016, Lester went 3-for-4o (with two doubles!), walked four times and had six more sacrifice bunts.
Then came the crazy Cubs/Mariners game of July 31, 2016. Brian Matusz started for the Cubs — his only game in blue pinstripes — and served up a two-run homer in each of the first three innings. The Mariners took that 6-0 lead into the fifth, when the Cubs scored a pair. It was 6-3 Seattle going to the bottom of the ninth. With one out, Anthony Rizzo doubled and Ben Zobrist singled him to third. A single by Addison Russell scored Rizzo to make it 6-4 and Russell took second on an error. Jason Heyward walked to load the bases and a force play at second scored Zobrist to make it 6-5.
Steve Cishek — a future Cub! — uncorked a wild pitch, scoring Russell to tie the game.
And that was it for a while. Neither team had a baserunner in the 10th or 11th, and Héctor Rondón set the Mariners down in order in the top of the 12th.
In the bottom of the 12th, Heyward led off with a double and advanced to third on a fly ball by Willson Contreras.
That brought up the pitcher’s spot. Joe Maddon sent Lester to the plate. Everyone in the ballpark knew he was there to try to squeeze bunt the run home.
And he did!
That’s really one of the weirdest walk-offs I can remember — a two-strike bunt from a pitcher in extra innings.
Lester wound up being one of the best free-agent signings in Cubs history, a huge part of the World Series team that year. He went 19-5 with a 2.44 ERA and finished second in Cy Young voting, then had three key appearances in the Series. Overall as a Cub, Lester posted 77 wins in 171 starts with a 3.64 ERA in 1,002.2 innings, one of just 30 Cubs in the live-ball era (since 1920) to throw at least 1,000 innings with the team.
After he left the Cubs as a free agent following the 2020 season, Lester bought drinks for Chicagoans at several different bars:
As it turned out, Lester’s final game — with the Cardinals, of all teams — was against the Cubs in St. Louis, Oct. 2, 2021. The Cubs won the game 6-5 after Lester had given them four runs in five innings, a grand slam hit by Trayce Thompson.
Lester has returned to Wrigley Field a few times since his retirement and appeared on Marquee Sports Network. The Cubs will likely have some 10-year anniversary celebrations of the 2016 World Series team in 2026 and I’d expect Lester to attend.
This series will continue on Monday.
