Friday will signal a passing of the torch as the Cubs take the field for the third straight October.
Jon Lester — the grizzled, battle-tested veteran — will be watching from the dugout as Kyle Hendricks — the unflappable, cerebral pitcher who looks more like an accountant — will take the ball in Game 1 of the NLDS against the Washington Nationals.
Joe Maddon announced the Cubs' rotation Wednesday morning, with Hendricks first, Lester second and then Jose Quintana and Jake Arrieta in order for Games 3 and 4 back at Wrigley Field early next week.
Here's what went into the decision for each pitcher:
Kyle Hendricks — Game 1
The 27-year-old right-hander led the Cubs in ERA in 2017 despite making only three starts in June and July combined due to a hand/finger injury.
Since he returned from the disabled list, Hendricks has posted a 2.19 ERA and 1.18 WHIP in 78 innings, permitting opposing hitters just a .658 OPS.
"Obviously Kyle's pitched really well," Maddon said. "We wanted to pop him right there."
Game 1 comes with all the "hoopla," as Lester called it, between the extra attention and build-up, plus the added wait time as each team is announced and the pregame ceremony lasts far longer than usual.
Hendricks, however, is the guy who beat Clayton Kershaw and the Dodgers to clinch the Cubs' first pennant in 71 years last October. Then he went out and started Game 7, helping to set the tone for the game that ended a 108-year championship drought.
He's watched as veterans like Lester and Jake Arrieta have prepared for Game 1s and wild-card playoff starts and knows what type of work is needed to get up for this game.
As for controlling his emotions? Hendricks will have butterflies of course — he is human, after all. But the Cubs have no doubt he'll be able to manage it.
"More eagerness, I think," Hendricks said. "Excited to get out there. You're gonna have a little bit of butterflies, for sure, but I think it's just that excited feeling.
"This is what you live for. This is the time of the year you want to play in."
Jon Lester — Game 2
Lester took the ball for Game 1 of all three postseason series last October and has a long history of success in the playoffs with three World Series rings to his name.
And while his last two starts of the regular season were more vintage Lester, he also missed two weeks in late August with a lat/shoulder issue and posted a 5.91 ERA in his first four starts off the disabled list to begin September.
Maddon admitted Lester's injury played a factor in the Cubs brass opting to go Hendricks over the 33-year-old 12-year veteran.
"Injuries have played a part in the way this has been designed," Maddon said. "Kyle's injury happened early enough in the year that he was able to overcome it and come back.
"...Part of what you're seeing rotation-wise right now is based on some unfortunate moments during the summer, but may actually benefit us moving forward."
With the off-days built in for Sunday and Wednesday, if the series does stretch to five games, both Lester and Hendricks would be able to throw Thursday on normal — or extra — rest.
"There's not a whole lot other than we thought Kyle's pitching really well," Maddon said. "Jon's last outing really showed where he's at — I think he's coming on. We could've done it the other way, we just chose to do it this way right now.
"Kyle's got some good numbers against this particular team and I have so much confidence with Jon Lester pitching in the postseason period."
Jose Quintana — Game 3
This is as much about Arrieta's hamstring as it is about Quintana.
The Cubs gave up a pair of elite prospects to secure Quintana's services for the next several years and hope he will be a part of their postseason rotations for years to come.
But he still hasn't appeared in the playoffs yet and the Cubs will give him two games and a few days to get used to the whole ordeal before he has to go out and execute.
This also ensures he is guaranteed a start and his first taste of pitching in October even if the doomsday scenario happens and the Cubs are swept out of the best-of-five NLDS.
Plus, Quintana was 5-0 at Wrigley Field during the season, even if he did have a 4.76 ERA in eight starts at the "Friendly Confines."
Jake Arrieta — Game 4
Arrieta hasn't been right since he walked off the mound on Sept. 4 clutching his right hamstring.
He was in the middle of another unconscious run before that fateful moment in Pittsburgh, going 7-2 with a 1.69 ERA and 0.95 WHIP in 11 starts in July and August.
Arrieta admitted he rushed back from the injury to face the Milwaukee Brewers on Sept. 21 and after an abbreviated start in St. Louis the next week, the Cubs opted to shut him down and forego his last start that was scheduled for this past Sunday, the final game of the regular season.
The plan at that time was for Arrieta to throw a simulated game Wednesday at Wrigley Field during the Cubs' NLDS workout, but that was shifted to a bullpen, partially because of a slick field after some Chicago rain, but also because they want to ensure Arrieta doesn't pus anything.
That bullpen went well by all accounts and the Cubs maintain there is no concern right now over him being forced to miss the NLDS. They just want to give him as much time as possible.
"Had Jake been well the whole time, this order would've been different, no question," Maddon said. "We just feel it's wise to give him the most time to rest his leg before we have to pitch him."