Cubs' Offer to Jon Lester Reportedly at Least $135 Million, Red Sox May Remain Favorites

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Cubs’ Offer to Jon Lester Reportedly at Least $135 Million, Red Sox May Remain Favorites

Chicago Cubs

jon lester feature red soxAs of this morning, pessimism on Jon Lester probably reached a new high, given the increasingly negative signals about the likelihood that the Cubs could actually land him. I wouldn’t quite say that changed as the day went on, but at least there’s a new angle to discuss.

Today, Dave Kaplan reported that the offer the Cubs have made to Lester is “significant,” which he specified as “north” of $135 million over six years.

Given that initial reports of Boston’s offer to Lester had the Red Sox going somewhere between $110 and $120 million over six years, I would absolutely characterize the Cubs’ offer as “significant.” Had the Cubs come to the table at five years and $100 million, then we would have known they weren’t really serious about actually landing Lester. This offer, if accurate, is absolutely serious, and is in the range of what folks were expecting Lester to get when the offseason began. (I’d hazard a guess that projections have gone up a fair bit since then, however.)

The cynical among you will probably remark that it’s convenient for the Cubs that this report is getting out, just in case they don’t ultimately land Lester (especially if he takes less than the Cubs have reportedly offered). I suppose that’s possibly true, but this is the time in the negotiation process – he’s received an offer from Boston, he’s met with the Cubs, he’s meeting with other teams, he could make a decision next week – when you’d expect an offer to leak.

Ultimately, I don’t buy the cynical angle on this one, because I think Lester is going to get more than 6/$135 million anyway. Indeed, shortly after Kaplan’s report, Bruce Levine wrote that an insider told him the expectation is that the annual value in Lester’s deal will reach $25 million. That wouldn’t surprise me at all. For what it’s worth, Levine’s source would not predict where Lester would go, but did say that the Cubs have been “on top of this situation from the beginning.” I suppose that’s nice to know, but, this time around, there never really was a concern that it was just a dog and pony show. The Cubs genuinely want Lester, and they will make sincere overtures – both in presentation and in offer – to get him.

But will they? Do they really have a shot?

Well, some tempering of any enthusiasm you might have allowed yourself to build:

What do we make of this stuff? Well, there could certainly be some gamesmanship at work. Maybe Lester’s folks leaked the Cubs’ offer to pressure the Red Sox (or another team) to come up. Or maybe Lester really does want to come to the Cubs, and all of the Red Sox talk is designed to get the Cubs to go to their absolute maximum. Or maybe Lester has always wanted to go to Boston, doesn’t necessarily need the highest dollar value to go there, and this entire process is about making sure the Red Sox at least make a fair offer, and about confirming that Lester doesn’t want to go to the other places.

In the end, I’m pleased to see that the Cubs have (reportedly) made a strong offer, and it’s at a level that I can wrap my head around it being worth the considerable roll of the financial dice.

But, I’ve got to be completely honest: I’m not sure I’d want the Cubs to go that much higher on Lester, given the other options out there in the coming months. Yes, Lester is awesome, and I understand why he might be the top target. But he’s still a pitcher over the age of 30, and, right now, it’s a lot of the Cubs’ available dollars to commit to a specific guy at a time when it might be more prudent to wait or to spread the money around. It’s no accident that the Cubs have emphasized at every turn this offseason that the quest to add impact pitching is not solely about this offseason.

A but to the but, being prudent with your dollars only matters in the end if you actually spend them somewhere. And with the way salaries are escalating, whichever pitcher(s) the Cubs ultimately sign will be attached to some crazy number. That’s just the reality, whether it’s now or next offseason or some hypothetical perfect year down the road.

I wouldn’t expect a final decision on Lester for a little while yet, by the way. He’s reportedly set to meet with the Cardinals, and now also the Giants, next week.

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.