Cost & effect: Why Jon Lester’s value remains high halfway through Cubs megadeal

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MIAMI — If you thought the Cubs winning the World Series was a baseball rarity, get a load of what might be unfolding as lefty Jon Lester takes the mound Thursday in their season opener against the Marlins.

Starting the back half of his mega-deal with the Cubs, Lester looks like a threat to challenge the long-held baseball wisdom that long-term deals for free-agent pitchers are, by definition, bad contracts in waiting.

He has averaged 32 starts per season, made an All-Star team and came within a few votes of winning the National League Cy Young award in 2016.

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He’s also 34 and only halfway through that $155  million deal, so he hasn’t completely cleared the Barry Zito-Mike Hampton zone yet.

But after a brief stretch on the disabled list with a lat injury late last season, Lester had his healthiest, strongest, smoothest spring as a Cub. And that “aging well” theory the front office talked about when Lester signed has played out so far, as Lester continues to reinvent himself.

“I remember him in Boston throwing 98 [mph],” said general manager Jed Hoyer, who was an assistant GM with the Red Sox when Lester broke in. “He’s learned how to compete exceptionally well with a much more varied arsenal than he had back then.

“Because of the fact that he’s already evolved somewhat once, I think he’ll be able to do it again.”

Whether he does — whether he even throws another pitch — it’s hard to argue that Lester hasn’t delivered full return on his value, at least as measured by the Alfonso Soriano Rule. If the Cubs can win just one World Series, it was said when Soriano signed an eight-year, $136 million deal after the 2006 season, it would be worth it no matter what he did after that.

“I think you have to be careful thinking that way when you go into a contract,” said Hoyer, who has teamed with Cubs president Theo Epstein on their share of bad free-agent contracts, from Julio Lugo and Carl Crawford in Boston to Edwin Jackson in Chicago. (The jury is still out on Jason Heyward’s eight-year pact.) “Jon’s been everything we could have asked for, and it goes beyond just the fact that we have a ring. He’s provided amazing stability for our team. He’s won huge games, and the kind of games he was brought in to pitch.”

Lester has nine postseason starts with the Cubs, another two postseason relief appearances, a 2.53 postseason ERA and appearances in the NLCS in all three of his seasons in Chicago. He was the co-MVP of the NLCS in 2016 on the way to that long-awaited championship, pitching three innings of relief in Game 7 of the World Series.

“I think none of this happens — ’15, ’16, ’17 — without us signing Jon,” Hoyer said.

Lester says that’s not enough.

“The reason I signed here was to win a World Series,” he said. “We’ve done that one out of three years, so I feel like the first three years have been a success.

“With that being said, I think there’s some unfinished things. I feel like we’re in a position to compete and succeed year in and year out, which we’ve done. If we keep doing what we’re doing right now, and I keep making my starts and pitching, everything else takes care of itself.”

Making those starts means 200 innings to Lester. That’s what made the lat injury as frustrating as anything else for him last season; it ended his streak of 200-inning seasons. It might also be why he pushed through the injury for several starts before eventually relenting and getting help from the medical staff.

It’s about durability — a focus, if not an obsession.

“That’s a big thing. That’s what we get paid to do. We get paid to pitch,” he said. “That’d be like paying a position player a bunch of money that never plays. That’s why I do everything that I physically can to be prepared on that fifth day to pitch.

“Last year, there came a point where I was hurting the team and I couldn’t fight through things anymore. When you do pitch a little banged up, keeping your team in the game has to be there. If you’re going to be out there like I was and constantly putting them behind the 8-ball early in games and then hurting our bullpen by only going four or five [innings], that’s not doing our team any service. That’s why I said something.”

Maybe that compromised finish is why Lester has taken on a look this spring that makes teammate Kyle Hendricks say “he’s on a mission.”

Lester doesn’t use phrases like that.

“But, yeah, throughout my career I’ve taken the ball,” he said. “At the end of the day, I can’t control

anything else. I can just control showing up.”

When it comes to long-term contracts, that’s usually what counts most. And it has most often counted against the Cubs, whether it was Kerry Wood’s health issues or Carlos Zambrano’s career slide after signing a five-year extension in 2007.

Not that Lester is looking for some kind of franchise’s-best-contract award.

“If, at the end of the day, that’s said, hey, that’s great,” he said. “But it’s not something I’m worried about. I want to walk away from this game knowing that, one, I was prepared every five days and, two, that guys say I’m a good teammate.

“That’s all, at the end of it, that I would want.”


How Lester’s six-year deal looks at the halfway mark compared to other current long-term contracts for starting pitchers who joined their teams as free agents (stats are season averages for current team):

Pitcher, contract GS IP ERA WAR*

  • LH Jon Lester, 6yrs/$155m (‘15-20) 32 196 3.33 3.00
  • RH Max Scherzer, 7/$210m (’15-21) 32.7 219 1/3 2.76 6.77
  • RH Masa Tanaka, 7/$155m** (’14-20) 26.3 167 3.56 3.18
  • LH David Price, 7/$217m (’16-22) 23.0 152 1/3 3.84 2.30

*From; **-Plus $20 million Japanese free agent posting fee.

Follow me on Twitter @GDubCub.


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