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A decade after breakout ’08, Cubs’ Jon Lester a different — and better — pitcher

Jon Lester has been the Cubs' best pitcher from the start of the 2018 season. / John Antonoff photo

The prologue to Cubs pitcher Jon Lester’s decade-long run as a big-league star reads like a novel in itself. It involves a promising 15-game debut as a rookie in 2006, a shocking cancer diagnosis that sent the then-22-year-old left-hander off the rails and a hair-raising comeback that culminated in a -winning start in the final game of the 2007 World Series.

But Lester didn’t truly break out until 2008. He won 16 games for the Red Sox that season, posted a 3.21 ERA and threw his first and only no-hitter.

Ten years later, Lester, 34, is a little more than halfway through what might be remembered as his finest season. At 11-2 with a 2.45 ERA, he is performing much as he did in 2016, when, in Year 2 with the World Series-bound Cubs, he delivered a career-high 19 victories and a career-low 2.44 ERA. The big difference: In 2018, he’s doing it as the unquestioned ace and linchpin of the Cubs’ staff.

So much has changed about Lester the pitcher over the last decade.

“More than anything, just thinking about it all makes me feel old,” he said. “You don’t realize how fast 10 years can go. It feels like yesterday that I was just trying to make my footprint in the sand in the majors.”

As he prepares to join his fifth All-Star team next week in Washington — where he won’t pitch in Tuesday’s game — Lester is eager to put the pedal to the metal in the season’s second half. But he didn’t mind throwing the ol’ time machine in reverse during a recent conversation about some of the differences between 2008 and now.

Prove it or lose it

Before his no-hitter that May, Lester’s performance was a bit rocky. By the end of April, he made more walks than strikeouts. The Red Sox were 5-5 in his first 10 starts. He wasn’t bad, though he worried about his job security.

“That was a tough season early on,” he said. “I didn’t throw the ball well. I thought I was going to get sent down.”

That wasn’t as misguided a notion as it would be in Year 4 of a six-year, $155 million run with the Cubs, but Lester’s concern was unnecessary. Those Red Sox didn’t have many — or any — clear options after Josh Beckett, Tim Wakefield and Daisuke Matsuzaka. Lester ended up being the only member of the rotation who didn’t miss a start.

Throw vs. grow

In 2008, Lester hardly could’ve been described as a student of the art and science of pitching. Picture the field as a classroom, the game as a test and Lester leaning over and copying the answers of veteran catcher Jason Varitek.

“I was just a thrower,” he said. “I had stuff but didn’t know how to use it, didn’t know how to execute it, had no idea about a game plan. I’d go over it with Tek before a game and whatnot, but I didn’t understand it.

“I was spoiled, too. Tek was the guy who did it all. Me being a young guy, I was like, ‘Yes, sir, I’m throwing what you put down.’ But there was no understanding on why. ‘Why does this succeed?’ ”


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Long gone are the days when Lester could rear back and find 96 mph of hit-this-if-you-can. Not until 2013 did he begin to get the feel for “attack points” with individual hitters that has helped inform his current, more cerebral pitching approach. Yet even when old-timer David Ross was his personal catcher in 2016, Lester tended to be deferential.

Now that he’s helping to bring along catcher Willson Contreras, Lester is much more the master of his own destiny. He wishes his intellectually curiosity had come out sooner.

“I can’t believe where I was at then and that I was able to succeed,” he said. “That’s what’s crazy. If I’d understood more about pitching at 25, maybe I could’ve been even better, more consistent.”

Nobody better … or older

This is the first time Lester has felt like a true leader and elder statesman of a pitching staff. Even after signing the megadeal with the Cubs, he was careful not to “step on the toes,” as he put it, of the likes of Ross and pitcher John Lackey.

“When those guys were here, even though you’re on an even playing field, it’s kind of like the elders thing — you always still have that respect for your elders and the guys who have done it longer than you,” he said. “You always still kind of bow down to them.

“But I don’t have that veteran guy over me now. It’s me.”

Rotation mate Kyle Hendricks saw a -different Lester from the first day of spring training.

“It was an on-a-mission look,” Hendricks said. “It was him thinking he needed to step up and be that ace — that solidifying force — even more than before. You know the work he’s going to do. You know the leader he’s going to be. You know he’s going to be that guy.”

Lacking his big buddy

Lester misses Lackey. They weren’t teammates yet in 2008 — Lackey didn’t pitch in Boston until 2010 — but there’s something of a hole in Lester’s heart this season. Or at least an empty chair in the clubhouse.

Lackey was a Cub in 2016 and 2017. The team didn’t have much use for him after that.

“I talk to ‘Lack’ pretty consistently,” he said. “He seems like he’s doing well. I get the text messages from him on the boat, having fun and living it up. I think he’s really enjoying it, but I’m sure it’s hard. When you take the competitiveness away, what do you do?

“But he was a great teammate, man. Lack was the best. He was my teammate the longest out of anybody I’ve ever played with. That was pretty special to be a part of.”

With the departures of Lackey and Jake Arrieta, Lester and Hendricks have bonded. Arrieta was tight with Hendricks. Neither Lester nor Hendricks is the type to really stick his neck out socially, so it took a bit of doing for them to come together.

“I don’t know who made the first move,” Hendricks joked. “Probably neither one of us. It just kind of happened.”

Seeing the finish line

There were times in 2008 when Lester felt as if he could pitch forever. These days, he’s becoming more aware that there’s an end of the road. Will he want to pitch after his Cubs deal ends in 2020? Will anyone want him?

“My biggest thing is I don’t want someone to dictate when I’m done,” he said. “Kind of what happened to Lack, I don’t want to come back and then not have a job. I want to be able to take that jersey off and say, ‘Here, there you go. I’m going home.’ ”

But first comes a trip to Washington. A few months after that, he hopes and expects, a fourth consecutive postseason run with the Cubs. It’s not that easy to think more distantly than that.

“If I feel good physically and think I can bring something to the table, maybe I’ll have a lot more baseball in me. But I don’t want to go out there and get my ass kicked, either. That’s no fun. Also, I don’t want to play for numbers. I’m not that guy. I don’t want to be chasing anything or worrying about any nonsense. I want to win the World Series.”