Jon Lester was itching for the opportunity to pitch one more game at Wrigley Field and put the team on his back once again in October.

It was not meant to be, as the Cubs ultimately didn’t host a Game 3 in the Wild-Card Series at “The Friendly Confines.” That means Sept. 16 might go down as the final appearance for Lester at Wrigley Field.

The Cubs are not expected to pick up the $25 million option on Lester for 2021, so there is no guaranteed path to a reunion with arguably the greatest free agent signing in the history of the organization.

But the Cubs are leaving the door open for Lester to return next season and the veteran southpaw has made it known he has interest in returning.

Theo Epstein plans to talk to Lester this week and the two sides will determine their next step forward.

“It remains to be seen whether Jon has pitched his last game as a Cub or not,” Epstein said in his end-of-season presser. “There’s certainly the possibly that he continues to call Wrigley Field home. But whether he leaves or stays, this is an appropriate time just to acknowledge the profound impact that he had on our organization.

“It’s rare when someone joins an organization with some clear goals in mind — to win a World Series, to change a culture, to show up in October just about every year and pitch really well in big games, to be a great teammate, to be someone the organization can be proud of, to make an impact on his teammates and in his community and accomplish all those goals in such an admirable manner.

“We owe him a great debt of gratitude. We were investing in Jon Lester the person every bit as much as we were investing in Jon Lester the pitcher and he came through in both areas for us in typical Jon Lester fashion. So huge tip of the cap to him. He’s made a huge impact on Chicago Cubs baseball and it remains to be seen what the future holds, but he’s someone I really admire and always will.”

As Epstein laid out, Lester’s impact on the organization goes far beyond his performance every fifth day on the mound. But there’s also a need on the pitching staff.

The Cubs have only two pitchers locked into the 2021 rotation in Yu Darvish and Kyle Hendricks, though Alec Mills and Adbert Alzolay are expected to get an opportunity to join that group. It still leaves room for a fifth starter and more depth.

Lester will turn 37 in January and is 7 wins away from 200 for his career. He went 3-3 with a 5.16 ERA in 2020 and finished the season on a strong note (3.92 ERA over final 4 starts).

The Cubs paid tribute to Lester during last week’s workout at Wrigley Field with a light-hearted video that featured Kyle Schwarber making “whoopsies” in left field during Lester’s starts. The video was Anthony Rizzo’s idea and designed to be a good-natured moment for the team to have fun with.

Kyle Schwarber loves being Jon Lester’s left fielder 😂 pic.twitter.com/nFoqC1Nw8h

— Marquee Sports Network (@WatchMarquee) September 30, 2020

Schwarber has been very complimentary of Lester and how the veteran took him under his wing as a rookie in 2015, buying him his first suit and showing him what it means to be a big-leaguer.

That video was one small example of the tremendous respect these Cubs players have for Lester and everything he’s meant to this franchise over the last six years.

Lester has unquestionably been worth every penny of the $155 million deal he signed before the 2015 season, joining a last-place squad and helping to lead that team to 97 wins and a trip to the National League Championship Series.

Lester also showed up when it mattered the most. Over his career, he is 9-7 with a 2.51 ERA and 1.02 WHIP in 154 playoff innings.

Those numbers have been even more impressive in a Cubs uniform: 2.44 ERA, 0.96 WHIP in 12 appearances (10 starts) for the North Siders. That includes heroic performances in Games 5 and 7 of the 2016 World Series.

The playoffs are where Lester’s intense competitiveness has shined the brightest and he credits guys like Curt Schilling, John Lackey and Josh Beckett for showing him the ropes with harnessing that fire into executing on the mound.

“I put a lot of emphasis on that fifth day — that’s my day,” Lester said. “That’s my time to go out and help the team. I’ve always looked forward to that and I guess that’s what kind of builds up the emotion, builds up the competition, the anxiety, everything.

“There are a lot of emotions that go through on that day that I want to pour out into a short period of time.”

Nobody knows for certain what will happen, but there’s a possibility Lester will get an opportunity to go out and perform on “his day” in a Cubs uniform once again next season.