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Has Cubs’ Jon Lester hit the ceiling? He’ll let you know after his 13th straight 30-start season

Lester is coming off his worst of five seasons with the Cubs, but he isn’t ready to throw in the sweat towel — nor is he fretting one bit about a gathering storm of doubters.

Lester no longer has his best stuff — nor does he consider himself the Cubs’ ace — but he still believes he can get the job done.
John Antonoff for the Chicago Sun-Times

MESA, Ariz. — Jon Lester knows a thing or two about hitting the proverbial ceiling.

The 36-year-old veteran of 14 major-league seasons and winner of 190 games — among active players, only Justin Verlander (225) and Zack Greinke (205) have more — doesn’t need anybody else to tell him when he’s out of gas, at the end of the line — that he has gone as far and as long as he could go.

The man has been there and done that, no doubt about it.

Just not in baseball. Oh, no. Not yet.

There are people out there who are convinced the Cubs lefty — the greatest free-agent signing in team history — can’t pitch a lick anymore. Lester is coming off his worst of five seasons with the Cubs, a trying 2019 campaign in which his innings (171 .2) were down and his ERA (4.46) and WHIP (1.497) belied his 13-10 record.

But dig this: He isn’t ready to throw in the sweat towel. Not on baseball, the sport he stuck with over a host of others.

Nor is he fretting — at all — about a gathering storm of doubters.

“I don’t need other people to motivate me,” he said. “I know that I’ve had a long career with a lot of pitches thrown, and I know my stuff isn’t what it used to be, but I still feel like I’m a very effective big-league pitcher.

“I know I’m not the ace of this staff, too, but you know what? I think that’s a good thing. I hope that maybe I’ve done something here to rub off on Kyle Hendricks or maybe rub off on Yu Darvish to allow them to take over that role.”

BUT BACK TO BASHING into the ceiling. Is it really necessary to spend a bunch of words rehashing Lester’s experiences in sports other than baseball? Heck, no. It’s just fun.

Before Lester was a pitcher, he was a player on the pitch. In Puyallup, Washington, he took up both baseball and soccer at age 6. A boy with natural athleticism who could run, he took to the latter sport, competing just a bit harder and scoring many more goals than the average kid. He continued in soccer through eighth grade — and had a real knack for it — but soccer and baseball were both spring sports in high school.

Not the most complicated choice: Lester could throw a baseball like nobody’s business.

Goodbye, beautiful game.

But his first high school sport was football. He’d been on the fence about trying out as an incoming freshman at Tacoma’s Bellarmine Prep until his dad finally told him to get his rear end in the car — this thing was happening.

Playing football for the first time, Lester won the starting quarterback job on the freshman team. He ran the option and had a natural feel for the rollout passes that were a staple of Bellarmine’s offense. As a sophomore, he competed for the starting spot on the varsity — until he blew out his right knee, an ACL injury.

So long, football.

And yet, there was basketball, too. It was Lester’s favorite sport and where he hit the ceiling the hardest.

His knee injury had cost him his sophomore hoops season, but he was able to pitch in the spring and fared so well that college baseball scholarship offers started to roll in. Still, he came back and had a terrific season on the court as a junior. He made all-conference, averaging more than 16 points per game as a wing with a decent shot and no qualms about cherry-picking for layups. He also played AAU ball at a reasonably high level — not a star but certainly a tough kid who could out-compete more talented players.

“Man, that was fun,” he said. “I loved that. I got to meet some really good guys doing that.”

It was — plainly speaking — more fun for him than baseball. But baseball was where Lester’s bread would be buttered, and he was smart enough to see the reality of things. So he sat down with his hoops coach a week before practices started his senior year and said he was going to go all-in on baseball.

He’d reached his ceiling in every other sport.

“That was tough,” he said. “It really hurt me. It was a hard conversation to have. I felt like I let the [basketball] team down, too.

“But I knew I was kidding myself. I didn’t have a chance to really do anything in any sport except baseball. So that’s when I became a baseball player, I guess. Everything else was over.”

AND NOW, HERE HE IS, with only a one-year option in his contract beyond 2020. The Cubs wouldn’t have won the 2016 World Series without him. They wouldn’t have this entire run of blissful relevance, beginning in 2015, without him. Baseball-wise, he’s not leaving this mortal coil unless, and until, he decides it’s time.

“It’s harder and harder every year, but I don’t want somebody to dictate for me when I’m done,” he said. “Whatever happens next year, with the option and being here, I would love to do that. But then the following year, I don’t want to go into the offseason and not get a call because none of the 30 teams want me. ‘Oh, I guess I’m done.’

“I can promise you, I’m not playing for stats. I’m not going to sign a minor-league invite to hopefully get up to X-number of wins. I’ll tell my teammates before it’s going to be my last start, but I don’t know if I’m going to tell the world. It’ll be up to me. I’ll decide when I can’t do this anymore.”

The short answer to that is his own version of 13 going on 30. Of all the numbers that go into defining a potential Hall of Fame career, it’s his streak of 12 straight seasons with at least 30 starts that means the most to Lester. He aims to make it 13 in 2020.

If he can do that? Let’s see anyone try to kick that brand of dependability to the curb.

“I like my teammates to know that, every five days, I’m going to be there for them,” he said. “That’s something I pride myself on, something I work toward. I want everyone in the Cubs organization, and especially everyone on that field, to know that, when my turn comes, I’m going to be running out there and giving it everything I have.”

Lester would also like to average at least six innings per start, something he failed to do in 2019, and find his way into the eighth inning . . . once? Hard to believe, but he hasn’t gone past seven innings in any start since the 2017 season.

He offers a couple of reasons why he just might be able to accomplish all of the above. One is the offseason work he did on his arm, hip and back with an Atlanta trainer he hired for the first time. Repeatedly during spring training, Lester spoke of being in a good place physically as a result.

Bigger picture: He’s done nibbling and back in attack mode. At least, those are his intentions.

Though his fastball is down three or four ticks from where it was during his Cy Young runner-up season of 2016, Lester still believes he can get right-handed batters out if he gets back to his career-long strength of pitching inside. Even last season, he generated a high swing rate on four-seamers and cutters in — and most of those pitches were off the plate. By his reckoning, he just didn’t throw enough of them.

“Last year, I started nibbling so much,” he said. “Backdoor cutter: ball. Sinker: ball. Changeup: strike. I’m behind in the count and letting them put their sights on me. I’m letting them win before the game has even started.”

Not anymore.

HEY, ABOUT 2016 and the team the Cubs beat in the World Series. You remember the Indians, don’t you?

“Yeah, we [expletive] hated Jon Lester,” said Jason Kipnis, the former Indians second baseman, after joining the Cubs this spring. “I’m kidding — sort of — but he had our utmost respect. We knew what kind of bulldog competitor he was. We knew when he pitched, we had to really focus on trying to scrape runs across any way we could.”

After sharing a clubhouse with Lester for a couple of weeks, Kipnis described their interactions this way: “I get the morning grunts from him.”

Kris Bryant, who was a Cubs rookie in 2015, the year Lester came aboard, can relate.

World Series - Chicago Cubs v Cleveland Indians - Game Seven
Lester in Game 7 against the Indians.
Photo by Ezra Shaw/Getty Images

“When I first got here, I was like, ‘This guy’s so mean,’ ” Bryant said. “He just mean-mugs you all the time. But as I got to know him, I realized how unbelievable the guy is in everything that he does.

“He’s provided so much for this organization and team, and people want to say he’s on the downturn? I see this guy every day. Just because it could be his last year, he’s not like, ‘I’m good.’ He’s like, ‘No, I’m going to make this the best damn year I’ve had here.’ I would never bet against Jon Lester.”

First-year manager David Ross, who was Lester’s personal catcher with the Red Sox and the Cubs, gave simple marching orders to his old battery mate at the start of spring training: Impose your advice, knowledge and experiences on this group. Do that, and it’ll be enough.

“I think I’ve treated him how I would treat my friend,” Ross said. “As somebody who’s gone through that experience of getting to the back end of his career, and knowing what kinds of things go through your head, I know the narratives you can create. Don’t get caught up in that. If this is your last year or if you have longer than that, don’t take it for granted. Take advantage of it.”

On his worst day, Darvish brings more pure talent to the mound than Lester had at his apex. Despite that, the Cubs’ best pitcher regards Lester with a fair bit of wonder.

“I can still see the cutter. I can still see the sinker. He’s still good enough,” Darvish said. “But the best thing is his [competitiveness]. He’s just special for me. He’s very special.”

There’s no doubt in the clubhouse when it comes to Lester, who’s 74-41 with a 3.54 ERA as a Cub and has dialed it up a notch at playoff time.

“What Jon brings presence-wise is a plus for this group,” first baseman Anthony Rizzo said. “Him on the mound is just different. I don’t care if he’s pumping 95 [mph] like when he was younger or he’s throwing 84 — when he’s on the mound, it’s different.”

And, you know, no pressure, big fella.

“I’m going to pen him in for 30-plus starts and anywhere from a high-2.00 ERA to a high-3.00 ERA,” Rizzo said. “And we’ve got to get him wins, because he’s got some monumental [stuff] going on.”

Career milestones? The Hall of Fame? That stuff isn’t in Lester’s head right now.

DIG THIS, TOO: In a heartbeat, Lester would sign up for every bit of his Cubs run if he could do it all over again. His somewhat disappointing debut season in 2015, when he felt he’d pushed himself too hard in the spring and never quite recovered. The storybook 2016 season. The slow, subtle decline since — which, by the way, included 18 victories, tied with Max Scherzer for most in the National League, in 2018. All of it.

“Hell, yes — 100 percent,” Lester said. “It’s been a lot of fun. Chicago has been great. It was relieving for me on just a personal level that we won the World Series the second year. If we’re getting into Year 6 and we haven’t won it, it’s like, ‘Damn, that’s what I came here to do.’ Now we’re looking for No. 2. We’ve just been a little short the last few years.”

For the first time since he can remember, Lester didn’t watch much of the playoffs last season. Instead, he went home to his farm in Georgia and zoned out. He took his kids hunting. He fished on the pair of lakes near his property.

Maybe he’s winding down. Or maybe he was just recharging.

“I’ve been doubted before,” he said. “I was never supposed to be the Game 1 starter of anything or an Opening Day starter. I was supposed to be a solid 3 or 4 in the big leagues and have a decent career. I don’t care if anyone is doubting me. Making those 30-32 starts, that’s all the motivation I need.”

Lester puts in work during 2020 spring training.
John Antonoff for the Chicago Sun-Times

Lester has three World Series rings, zero Cy Young awards and zero 20-win seasons. Want to guess how much he cares about those shortcomings? The answer comes with a zinger at the expense of MLB commissioner Rob Manfred, whose klutzy minimizing of the World Series trophy last month while acting as an apologist for the cheating Astros will live on in baseball infamy.

The answer, for those scoring at home, is that Lester cares zero about the notches that don’t appear on his own belt.

“My whole career, people told me I’m not a No. 1, I’m not an ace,” he said. “I’ve just taken it as, ‘I’m going to prove you wrong, going to prove you wrong by the way I go about it.’ I don’t have Verlander’s stuff, but I’ve out-competed people. I pride myself more on that than anything.

“Yeah, it would’ve been nice to have one of those [Cy Youngs] and put it up on the mantle. But I’m sure you can ask guys who have them but haven’t won a World Series — they’d trade me for them in a heartbeat. I wouldn’t trade one of those ‘pieces of metal’ I’ve got for a Cy Young or 20 wins any day.”

So, he prepares. He grunts. He gets himself all lathered up for yet another go-round. Soon — soon-ish? — it’ll all be over. The critics will have their day.

“When I get done and I sit back?” he said. “I’ll look back at what I accomplished in this game. Then maybe I can say, ‘Screw you guys. I think I did all right for myself.’ ”