Jon Lester on Possible Final Wrigley Start: ‘I Didn’t Think 6 Years Would Go This Fast’

Whatever harbinger is the opposite of the canary in the coalmine, that’s what Jon Lester was for the Chicago Cubs. More than any player before or since, his decision signaled to the rest of the baseball world that the organization still sitting in the ashes of the decrepit building Theo Epstein had burned to the ground was for real. Six years later, the dimming flame of his career may signal the passing of the torch to a new era of Cubs baseball.

Two years after he signed, along with the man ostensibly brought in to help lure him as a personal caddie, Lester helped lead the Cubs to the World Series. Four years after that, he’s working for his former caddie to get a slightly different version of their old team back there following a wild 60-game season that may not see him pitch at Wrigley Field again.

The lefty won’t take the mound when the Twins come to the North Side over the weekend for the final three home games of 2020 and there’s no guarantee he’ll be one of the Cubs’ three starters in the opening round of the playoffs. The first two spots are locked in, but the third could go to Alec Mills, who just authored a no-hitter in Milwaukee after an excellent outing in his previous start.

An abbreviated postseason series is no time for friendship to rule the day, so David Ross isn’t going to be playing favorites. Lester will make at least one more start, though, so it’s possible he’ll prove himself worthy of a playoff nod. But even then, winning the first two games would seal the deal in that series. After the Cubs host the opening round, play moves to neutral sites in Texas the rest of the way and Wrigley will be a memory.

“This year hasn’t been easy for a lot of reasons,” Lester told the media after the win. “I’m not going to sit here and say ‘Woe is me’ because there’s a lot of people worse off than me.

“I didn’t think six years would go this fast.”

Damn right it did. So fast Lester never completely transitioned from the tendency to put a Boston accent on his name that makes people, or at least me, want to call him Jawny Lestah. I mean, if were a true Chicagoan, he’d be Jahn Lesters. You know what, though? He still had that extra s, he just wore it on his chest as he lifted an entire organization up with a quiet strength we might never fully appreciate even when we actively try to fully appreciate it.

Jonathan Tyler Lester, a man so unassuming that his Players Weekend nickname read simply LEFTHANDER, will go down as the greatest free-agent acquisition in Cubs history. And this is a team that inked Andre Dawson for a pittance. But back to that nickname, the significance of which is revealed in its simplicity. There are plenty of other southpaws on the Cubs roster and elsewhere in the league, but everyone knows damn well who you’re talking about when you use “Lefthander” as a name.

Were it just a matter of his line Wednesday night, Lester’s final outing would have been a perfectly fine way to go out. He went five innings and gave up two runs on four hits and a walk, striking out one in the process. As he’d surely say, his team getting the win mattered more than his stats anyway. But the fact that he had to walk off the mound to the inauthentic din of piped-in crowd noise will probably take a little while to digest.

“That’s probably the most frustrating part,” Lester said when asked about the absence of fans. “Going back to ’14, I didn’t really get to walk off the field like wanted to at Fenway. Having an empty stadium, not really how I envisioned possibly my last start here.”

Remember, he was traded to Oakland prior to the deadline in 2014 when the Red Sox didn’t sign him to an extension. It was that move that forced him to cope with the reality that he wouldn’t play his entire career in Boston, which had hoped to be able to re-sign him that winter. Instead, his newly broadened horizons brought him to Chicago and cemented his legend.

It’s impossible to avoid a sense of melancholy as you bear witness to the decline of star in real time, watching as their light flickers like a fluorescent bulb with a bad ballast. Even so, the hope remains that the light holds out just long enough for you to reach the exit. And maybe if you’re lucky, you’ll get to see than final coruscation when they shine just as brightly as in their prime.

If only we could have shared that together in person this season, to have lifted Lester up with our hearts and voices just as he’d done so many times for all of us with his performances. He deserved that much, and the fact that he couldn’t feel that appreciation radiating from a packed house at Wrigley as he walked off the mound for a final time is just the latest blow in the incalculable series of them this asshole of a year has dealt us.

So while I know it won’t reach him, the only way I can see fit to close this is to say thank you. Thank you, Jon, for everything you did for the Cubs and all the fans over these last six years. You allowed us to experience moments many of us never truly believed were possible and for that you have earned our eternal gratitude, even if we never got the chance to tell you in person. You will be missed.

Now get back out there and win us another one.

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