Are the Chicago Cubs Interested in Jon Lester as a Free Agent? What Happens If He’s Traded This Week?

jon lester feature red soxIt wasn’t because of the Jake Peavy trade, which was probably coming regardless of the Boston Red Sox’s plans for the Trade Deadline. It probably is more because of the losing, and the recognition that now is the time to plan for the future.

Whatever the case, the possibility that the Red Sox sell off anyone they can who isn’t under contract beyond this year (or who is a mere complementary piece) has increased in recent days.

And the big name that falls into that category is ace lefty Jon Lester.

If the Red Sox decide to trade Lester, whom they’ve not been able to extend after this year, it’s going to be a very interesting decision with long-reach implications. For one thing, it’ll shake up a playoff race, but there’s obviously very little impact there to the Cubs. More importantly, a trade would virtually ensure that Lester reaches the free agent market, something that was not expected even six months ago. A trade would also ensure that Lester is uncoupled from draft pick compensation, which could increase his price on the free agent market.

To that point, let me just offer that *if* you are hoping the Cubs go after Lester, you’re going to want to hope that he isn’t traded (and isn’t extended), and does become tied to draft pick compensation. Why? Because the Cubs are likely to have a protected pick next year, making the effective price to sign Lester a little less for them than for teams that draft in the 11 to 30 range. If Lester cannot be made a qualifying offer because he’s been traded, the field will be leveled for all teams.

But are the Cubs even interested in Lester? Is it worth watching what happens this week all that closely?

Well, not only did Ken Rosenthal recently report that the Cubs sent high level evaluators to watch Lester face David Price (of course, the Cubs could have wanted to see Price as much as Lester for 2015 purposes), but also Gordon Wittenmyer writes that the Cubs have had “significant” internal discussions about going after Lester (as well as Justin Masterson, who has to look like a reclamation type after his ugly season).

Lester, whose dominant performance this year does make you a little nervous when you dig really deep, turns 31 before the start of next season. He looks to be a three or four-win pitcher for another few years yet, and is a guy you’d love to have in the rotation, even if not as your number one. That the Cubs would be considering him is understandable.

Whether it proves to be a good idea to pursue him is another matter entirely, and I’ll reserve judgment on that until the offseason approaches and we’ve got a little more data on what that pursuit – and price – might look like. Right now, we know only that Lester reportedly rejected a four-year, $70 to $80 million offer before the season. Does that look cheap now? Will it in November?

And that’s why, in part, seeing what happens with him this week is pretty important. If Buster Olney is to be credited, we could see something happen:

Maybe this week will be exciting after all.

written by

Brett Taylor is the Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and on LinkedIn here. Brett is also the founder of Bleacher Nation, which opened up shop in 2008 as an independent blog about the Chicago Cubs. Later growing to incorporate coverage of other Chicago sports, Bleacher Nation is now one of the largest regional sports blogs on the web.

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