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jon lester feature red soxThere are so many grains of salt with which you need to take this report that it is diluted to almost no meaning …

HOWEVA, it’s a very interesting topic, and the rumor, itself, is very interesting as well. So let’s discuss it.

Ken Rosenthal reports, via a video at FoxSports, that the Cubs’ willingness last week to take on Cole Hamels’ contract via waivers (a deal did not happen) is “telling” about the Cubs’ ability to spend big, and “some of Lester’s former teammates, meanwhile, already project that he’ll end up with the Cubs, reuniting with Theo Epstein and Jed Hoyer.”

First, those ample grains of salt:

  • How much could Lester’s former Red Sox teammates really know about his or the Cubs’ plans in free agency, when neither side is technically able to talk to each other yet?
  • How many former teammates? Are they close with Lester? Are they speaking from personal knowledge on things Lester has told them, or are they just connecting dots and speculating?
  • It’s August, and, while we do know that the Cubs have been scouting Lester (something teams frequently do in the final months before free agency (since it’s the last set of data points you can get)), it still seems pretty early to say that the Cubs will aggressively pursue Lester, let alone to say they are any kind of favorite.
  • Other teammates than the ones with whom Rosenthal spoke, apparently, have predicted that Lester will actually wind up returning to the Red Sox. It’s rare, but they say Lester is a different animal.

With those out of the way, it’s interesting to hear the Cubs and Lester connected by folks who could be in a position to know what Lester is thinking. Should the Cubs make a competitive financial offer, you can certainly see how they would be an attractive team for someone like Lester: burgeoning young core of talent, chance at doing something very special, familiar front office, great city, etc.

The real question is whether the Cubs are going to want to step up a $100+ million offer for Lester, who will be 31 next year. To date, this front office has shown a reticence to go over the top on free agents on that side of 30, but it’s entirely conceivable that, as we see the organization at an inflection point, they may decide that now is the time to take those kinds of chances. After all, if you want a front of the rotation arm, there are only so many ways to get it.

Lester as a future Cubs target has come up a few times before, and, outside of some modest concerns about his dominant season in 2014 not being quite as dominant as it seems, he does look like an attractive target. He’s been healthy and effective for seven years running, and he isn’t seeing any kind of surprising and significant velocity dip as he enters his 30s. If you’re going to bet big on a 31-year-old pitcher, Lester seems like as good of a bet as there will be out there in free agency (which is not to say some other guys don’t look good, too).

Having been traded by Boston, Lester is untied to draft pick compensation, and will not cost his signing team a draft pick. Some say that’s a good thing for the Cubs, who have been reluctant to part with draft picks to sign qualified free agents.

To me, however, I’m not so sure it’s a benefit. The Cubs project to have a protected first round pick (meaning, if they sign a qualified free agent, they give up only a second rounder), whereas 20 teams – some of the biggest markets among them – do not. That gives the Cubs a relative signing advantage against those other 20 teams when it comes to qualified free agents (i.e., the “price” for the Cubs is less onerous). Further, while we love to dream on second rounders, when their projected value is stacked up against a top tier free agent, you see how quickly those second rounders’ true value slides down the scale. In this particular context, a second round pick simply isn’t all that valuable to have, or painful to lose. Now, on Lester, the Cubs are on equal footing as every other team. Will that matter? Maybe not. But it would have been an advantage.

Ultimately, I expect the Cubs will be involved in Lester’s free agency, as will be a number of other teams.

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