Five winters ago, Jon Lester signed a $155 million deal with the Cubs to come in and lead their pitching staff and help form a winning culture in the clubhouse.
He's done exactly that and been worth every penny of the contract to date.
But as Lester enters what might be the final chapter of his Cubs tenure and just a couple days after his 36th birthday, what is the team expecting from him in 2020?
It's easy to look at Lester's stats from 2019 — league-leading 205 hits allowed, 4.46 ERA, 1.50 WHIP — and believe age is catching up to him and regression has set in.
The Cubs aren't buying that.
"We're not in the least bit writing him off," Theo Epstein said last month. "We're not, like, hoping he can hold his own. He's capable of being a really, really impactful pitcher for us."
Sitting in his hotel suite in San Diego for the 2019 Winter Meetings, Epstein reflected on his position five years earlier in the same city when his front office locked up Lester and officially began a new era in Cubs baseball.
"Being back here in San Diego has led a number of us to think back to that signing," Lester said. "We've had quite a few discussions of what a great job he's done living up to that contract and then some: How important he's been to all the good things that have happened the last five years — the big games that he's pitched for us and the consistency that he's given us.
"And the fact that he's still a vital member of the team going into the last year full guaranteed year of the deal says a lot about him and that work ethic. If you ask him, I think he's holding himself to the same standards that he always does — he hates losing, he wants to win, he's gonna work extremely hard. He pitched some really good baseball games last year. I think he can still be really successful with the stuff he has now."
Lester has lost a couple mph on his fastball and he has nearly 2,700 big-league innings under his belt (including playoffs). He is set to make $20 million in 2020 and the Cubs have a $25 million team option for 2021 that becomes fully guaranteed if he eclipses 200 innings this season (the deal also has a $10 million buyout).
Lester was an All-Star as recently as 2018 and watched his strikeouts climb back to solid numbers (8.7 K/9) after a dip in whiffs in '18. But too often opposing batters were squaring him up when making contact, as evidenced by a career-high 38.7 percent hard-hit rate.
With Yu Darvish's fantastic second half and Kyle Hendricks' continued steady production, the days of Lester serving as the Cubs' "ace" are probably behind us. But — as Epstein said — the team is still counting on him to play a big role in 2020. Bet against the wily veteran at your own risk.
Lester has been forward about how he's a different pitcher now than he was when he first came to Chicago. As he's aged, he's had to make adjustments to find ways to get hitters out without just relying on his stuff.
At the end of last season, Lester said he felt he and the Cubs found some things, but wished they would've made the adjustment sooner.
The Cubs value Lester's remarkable consistency and feel like his stat lines don't always tell the whole story. Even if he's not pitching into the seventh inning each outing, there's still something to be said for a guy who takes the ball every fifth day, gives his team a chance to win and sets the tone professionally in the clubhouse.
"What Jon's been able to do is implement a few new things and evolve, still keeping the Jon Lester status quo — the same things that have made him successful and what his strengths and weaknesses are, but using some pitches in some different ways that he maybe didn't in the past," pitching coach Tommy Hottovy said on the CubsTalk Podcast this week. "One big one for him and a pitch that really, really played well for him last year was that backdoor cutter that he really started implementing to right-handed hitters.
"When you watch guys — especially right-handed hitters — attack Jon Lester, the gameplan for the most part is: Look, he's gonna pound you in, he's gonna force you in there, he's gonna run the cutter in deep, so you get guys swinging at pitches in off the plate at a high clip off Jon. And every once in a while, you'll see a guy just drop his hands in and fist a double down the line when Jon makes a great pitch. But what that does is open up the outer part of the plate. It's one thing that Jon did a lot better last year — employing that backdoor cutter, commanding the fastball down and away, the changeup down and away, kinda exploit some of that.
"And to just continue to change as you grow. The Jon Lester we've always seen with that cutter than can eat you up and now he's learning, OK, this is how to use it in different situations and how he moved the ball around with that pitch and continuing to use it in the same location."
Lester has an entire offseason and spring training to work with Hottovy and the Cubs to make these adjustments and figure out how to keep Father Time at bay for at least one more season.