You’ll know President of Baseball Operations Theo Epstein finally has the Chicago Cubs ready to make a run at ending their 106-year championship drought when he strikes a deal with an old associate of his: Jon Lester.

Granted, we’re technically in the realm of “if” rather than “when.” The Cubs aren’t any more assured to sign the 30-year-old left-hander than any other club eyeing him in free agency.

The Cubs are definitely in line for Lester, though; Bruce Levine of 670 The Score says the two sides are ready to meet formally:

It was going to come to this eventually. The rumor mill has been linking Lester and the Cubs for months, with the connection between him and Epstein from their days with the Boston Red Sox often cited as a potential deal-maker.

For his part, Epstein hasn’t been shy about his desire for a No. 1 starter. He told Patrick Mooney of CSN Chicago the following in October: “You get aggressive and you try to find the right players. You don’t put a deadline on it. You don’t say: ‘We have to come out of this offseason with a No. 1 starter’ or you lock yourself into a bad deal. But over time, when the opportunity’s there, you pounce on it.”

Lester fits the bill of a guy for the Cubs to pounce on. In 32 starts for the Red Sox and Oakland A’s in 2014, he posted a 2.46 ERA across 219.2 innings. Over his last 51 starts overall, his ERA is 2.50.

Now, Mooney acknowledged that the Cubs could wait until next winter—when David Price, Jordan Zimmermann, Doug Fister and Jeff Samardzija could be availableto pursue an ace. And even if they do go after an ace this winter, maybe they’ll trade for Cole Hamels or sign Max Scherzer or James Shields instead of Lester.

Which leads us to two questions: Why now, and why Lester?

That first question is easy: Why wait when the Cubs are ready to break from their rebuilding phase now?

Sure, they only went 73-89 in 2014. But that involved a respectable 33-35 finish in the second half, a run that was largely characterized by the team’s offensively focused rebuilding effort beginning to bear fruit.

Established cornerstones Anthony Rizzo and Starlin Castro both had excellent second halves, hitting over .300 with OPS’s of .978 and .804, respectively. And while all three had their growing pains, top prospects Javier Baez, Arismendy Alcantara and Jorge Soler arrived to combine for 24 home runs.

Following in their footsteps in the near future should be Kris Bryant, who won Baseball America‘s Minor League Player of the Year Award for 2014 on the strength of a 1.098 OPS and 43 homers. When he takes his place at the hot corner, the Cubs are going to have young, high-ceiling hitters at six of eight spots.

You could see this Cubs-topian future forming during the team’s strong second-half run, and Rany Jazayerli of Grantland nailed it when he wrote in August: “If they do sign a Max Scherzer or a Jon Lester this offseason, the Cubs won’t just be a sexy pick to make the playoffs in 2015 — they might be a smart one. This franchise is a whole lot closer to being a contender than most people realize.”

The missing link may indeed be that simple.

The Cubs recently picked up arguably baseball’s best manager in Joe Maddon. They definitely have hitters. In Hector Rondon and Pedro Strop, they have the foundations for a dangerous bullpen. With Jake Arrieta’s 2014 breakout having established him as a top-of-the-rotation starter, the Cubs will have a one-two rotation punch as good as anyone’s if they add an ace this winter.

To that end, Lester being a perfect fit for the Cubs goes beyond just the numbers he’s put up recently.

For beginners, there’s Lester’s cost. He probably isn’t going to come as cheap as Shields, but he’s bound to cost less money than Scherzer. Given that acquiring Hamels would likely require a $100 million commitment and a sacrifice of several top prospects, Lester should be cheaper than him too.

Even more important, though, is how Lester comes off as a good bet to age well.

Obviously, there’s a built-in injury risk with every pitcher. But Lester has never suffered a major arm or shoulder injury, and he has made at least 30 starts every year since 2008. The concern is of that workload catching up to him, but his 6’4″, 240-pound frame and low-effort delivery help alleviate it somewhat.

As for how Lester’s stuff will hold up, that’s admittedly always more of a concern with power pitchers. Power stuff doesn’t tend to age well, and some (see Verlander, Justin) have trouble adjusting to life without it.

But that’s the hidden beauty of Lester’s 2014 season. In it, he proved that he’s already capable of being dominant without power stuff.

Per FanGraphs, check out Lester’s velocity in 2014 compared to the three prior seasons:

Lester hit his age-30 season, and BAM! His velocity went south. That’s ordinarily a recipe for the struggle becoming real, not a 9.0 strikeout-per-nine rate, a 2.0 walk-per-nine and, of course, a 2.46 ERA.

Success like that is either the product of a whole lot of luck or a transformation. In Lester’s case, it was the latter.

Shane Ryan of Grantland did a fine job illustrating what Lester was all about in 2014. He was better than ever not just at spotting his fastball and cutter, but at using the movement of the two pitches to toy with the edges of of the strike zone and, thus, with opposing hitters. Also, he only threw his curveball where hitters could do little except swing over it.

Here, these moving pictures can illustrate the point:

Lester’s new-and-improved approach not only led to his best swinging-strike rate since 2010, but also much weaker contact. Which leads us to Ryan’s conclusion: “And that, of course, comes down to location, particularly with the fastball and cutter that make up the bulk of his arsenal. He’s maximized his natural talent, achieved a kind of wisdom about how to use his pitches, and stands now at the apex of his career.”

The gist is that Lester has evolved. He still has very good stuff, but it’s made that much more dangerous by location and deception. Those are two talents that aren’t necessarily as doomed by age as power is. This is also where Lester differs from Scherzer, Shields and Hamels.

They’re in Lester’s age range, but all three sat in the 92-93 level with their heat in 2014. That’s above-average velocity, and they’re going to continue to be excellent pitchers as long as it holds. Excellent enough, even, to outperform Lester in 2015.

But in the long run, that above-average velocity will inevitably go away. When it does, that could be the reason why their talent didn’t age as well as Lester’s.

Certainly, every team interested in signing Lester is going to be mindful of his long-term outlook, and here’s guessing that I’m not the only one who’s thinking it looks pretty darn good.

But for the Cubs, Lester’s long-term future is doubly important.

The Cubs wouldn’t just be signing Lester to go for it in the short term. The idea would be to have him atop their rotation for the long haul as the team looks to build an empire in the NL Central. That Lester’s long-term performance projects as being equal to the task is reason enough to sign him. 

But it’s easy to think about Lester also being something of a staff wizard in addition to a staff ace. As a guy who’s turned himself into an ace pitcher with command and smarts, Lester could conceivably be a part-time pitching coach who teaches valuable lessons to any young hurlers who come along.

The Cubs really aren’t far off from being a contending team as they’re situated now. If they sign Lester, they’ll have taken care of the missing link and should reap the benefits for years to come.

Assuming Epstein already knows all this, he won’t let Lester leave next week’s meeting without an offer he can’t refuse.


Note: Stats courtesy of unless otherwise noted/linked.  

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