Lester links: What analysts and experts are saying

…this was the guy they more or less had to get to make that push toward contention a reality for 2015 and beyond. Jon Lester is coming off his best season to date, with a career-low ERA and walk rate, as well as his highest strikeout rate since 2010 (though everyone’s strikeout rates have been rising). In 2014, he returned to the formula that first brought him success: pitching more with his cutter and curveball, de-emphasizing the four-seamer and barely using his changeup. His cutter is the difference-maker among his pitches and the reason he’s actually a little better against right-handed batters than lefties, though he has plenty of breaking ball to keep lefties honest. His fastball command was much better in 2014 as well, though that seems harder to explain than the success he had from altering his pitch mix. He has been very durable; he reached 31 starts and 191 innings in each of the past seven seasons. The Cubs desperately needed something more than a fourth or fifth starter to join Jake Arrieta in their rotation, and Lester is a legitimate ace who adds five or six wins over in-house candidates for the rotation, such as Kyle Hendricks or Jacob Turner…

…there really is no way to spin this, no silver lining to sit on, no explanation that makes everything look better. Last winter, Lester — one of the greatest pitchers in the history of the Red Sox, coming off one of the best postseason performances we had seen before Madison Bumgarner raised the bar for everyone — was emotionally entrenched in Boston. It is where he had started his major league career, where his cancer had been treated, where he shared in the failures of 2011 and 2012 and in the Boston Strong title of 2013. Lester had a bond with the team and as he prepared for the last season before reaching free agency, he did something that makes agents cringe: He talked out loud about how much wanted to stay. Last January, he told reporters he wanted to work out a long-term deal with the Red Sox. [snip] The Red Sox offer: $70 million over four years. Look, it’s all Monopoly money to some degree. Nobody really needs more than $70 million. But the Red Sox offer was a universe away from the Cain deal — was less than two-thirds of the chunk that Cain had received for his free-agent years. It was less than half of the Hamels deal. It was one-third of the size of the $215 million contract that Clayton Kershaw got from the Dodgers.

The Cubs inked Lester for $155 million. According to reports, the Red Sox offered the same number of years, but $20 million less. What that makes it sound like is a desperate overpay. In reality, the numbers don’t make it look godawful. Depending on what you do with them, this might even look totally normal. For example, consider what ZiPS has to say about Lester’s next six years:

This is where we get into the art of things. The last three years, Lester has averaged about 4.5 WAR. On one hand, you’d want to project a decline, but on the other hand, Lester is also coming off by far his best season of the three, with some demonstrable changes to his approach. It wouldn’t be unreasonable to figure Lester might be a 4.5-win pitcher next season. What if you set the cost of a win at $7 million, and then inflated by the customary 5%? Then given the standard half-win per-season decline, Lester would be worth about $151 million. And what if you set the cost of a win at $7.5 million? The market’s been pretty crazy so far. Then you get Lester being worth about $162 million.

The Lester move — and to a lesser extent the unexpected hiring of Joe Maddon just prior to that — changes all of that. They are signals to Cubs fans that the time to win is now, their team is credible and not laughable and that they expect to contend. After all, one does not spend $155 million on a pitcher and toss aside the manager they just hired a year ago for a big name like Maddon with the expectation of improving to .500. But the other side of that credibility coin is pressure. No matter how many moves a team makes, it’s hard to improve by the 20 wins or so one would expect the Cubs will need in order to pull off the worst-to-first trick. And for all of the promise the folks who salivate over prospects have felt around this club, they were the worst team in the NL Central last year. And they still have some issues that need to be addressed. The pitching, primarily, as Lester is still mortal and can’t take the hill every second or third day. Prospects are great, but sometimes they don’t pan out as promised. For as excited as the Cubs and every Cubs fan has a right to be today, each offseason there are teams which make big splashes that cause everyone to crown them the offseason champs. Very, very often, however, those plans don’t survive engagement with the regular baseball season.

The waiting is over. The Cubs are back. Wrigley Field is alive. Lester, manager Joe Maddon and Co. are not simply going to aim for 2017 and wait for some of the game’s top offensive prospects to develop. No, the Cubs are going for it, and they’re going for it now. Rest assured, this will not be the Cubs’ last move. They’ve been talking to some of Lester’s former Red Sox teammates, free agents such as catcher David Ross and outfielder Jonny Gomes. And they’ve got the prospect power to acquire more pitching (Johnny Cueto? Jordan Zimmermann? Aroldis Chapman?) or a big bat (oh, what the heck, Troy Tulowitzki?).