jon lester feature red soxFor a few days, it seemed like the Jon Lester pursuit was going to come to a conclusion at any moment. And then the Dodgers jumped into the bidding, and everything got a little blurry.

That’s not to say that the Chicago Cubs were about to land Lester before the Dodgers stuck their gold-plated nose in, but it did look like they had a decent shot. Now? Well, the Red Sox and Giants always seemed fairly legit, and the Dodgers have so damn much money. It’s dicey.

But the Cubs aren’t going down without a fight. According to a Jesse Rogers source, the Cubs have made an offer that exceeds the previously-reported six years and $130 to $140 million range.



That’s good to hear, as it never seemed likely that Lester would be signing for less than $150 million. The problem, though, is that most expect Lester to get at least a littleĀ more than $150 million, and Rogers suggests that the Cubs don’t plan to keep up “if a team completely blows past that number.”

Separately, Bruce Levine suggests that Lester’s price tag is already at six years and $25 million per year (that’s $150 million), and the Cubs have “little wiggle room” if the bidding tops $155 million. The implication there is that $155 million is something of a soft cap for the Cubs on this bidding.

These situations are tough because, as a matter of negotiation principle, you have to draw lines. If you have it in your mind that you will absolutely, no matter what, get the guy, then, if the other side has any negotiation skills at all, you’re going to wind up paying far more than should. Maybe even more than you had to, because you can’t know whether the other side is merely posturing for more money once you’ve already gotten past a level they would be willing to accept. You’re willing to go to $160 million after deciding it’s just another $10 million? Well, then how about $170 million? After all, that’s just another $10 million. And what about $180 million? You see the problem in negotiating without a line.

If the Cubs draw a hard line at, say, six years and $25 million per year, with a club and/or vesting option for the seventh year (say also at $25 million) with a $5 million buyout, are you satisfied by that? As the weeks drag on and the numbers start climbing, it’s easy to lose sight of your valuation foothold – indeed, Scott Boras has made a living with that very strategy – but it’s important to step back. Six years and a guarantee of at least $155 million is a huge offer for a (to be) 31-year-old starting pitcher. There’s a ton of risk built into that offer, and I’ve got to be honest, I’m not sure how much higher I could see the Cubs going where I wouldn’t start to become concerned that the risk is going to outweigh the upside. The Cubs have a lot of financial flexibility and even greater flexibility is on the way in the coming years … but … I don’t know. Even if the Cubs quickly become a $150 million payroll club (and that’s a stretch for at least a couple years, in my opinion), that’s still one aging pitcher taking up more than 15% of the entire payroll.



For now, I know that if the Cubs were to get Lester on the kind of deal I’m talking about, I’d be happy. Yes, it’s a huge amount of risk, but I’ve got to believe the Cubs wouldn’t do it unless they felt like they were in a strong position to absorb the blow if Lester’s elbow pops a week after he signs. Beyond that 6/$155 million level, though? For that amount, the Cubs could probably get James Shields AND Brandon McCarthy AND Brett Anderson. Sure, you’d rather consolidate the talent into one player, but you’re also consolidating the risk.

And, I know I keep coming back to it, and it sounds like an excuse, but there really are so many other impact pitching options available over the next 15 months. There are ways to improve in the near and long-term with Jon Lester if need be.

That turned into quite a pile of pontification, didn’t it? Your TL;DR: Cubs are probably willing to go to 6/$150 to $155M for Lester, which is the floor of where I always saw this thing going. I’d be happy if they could get him at that level. Beyond that, I’m not sure it’s the best use of resources for the Cubs right now.

All right. Some other Lester-related bits floating around …

  • Jon Heyman writes about the mystery of the Dodgers. Just how aggressive are they being on Lester? And how serious are they about cutting payroll from its currently-projected $240 million level? Maybe not very, as Heyman says the Dodgers – not the Cubs – were actually the runner-up on Russell Martin, having bid four years and $74 million (the Cubs were closer to 4/$65-70M, and Martin ultimately went to the Blue Jays for 5/$82M). That’s a huge AAV offer for Martin, and it makes me think there’s nothing to stop them from going way over the top on Lester if they want. That doesn’t mean they’ll get him, as there remain questions about whether Lester would be interested in going to L.A., whatever the price.


  • Joel Sherman writes that sorting out the fact and fiction in this race for Lester is really difficult, because you can hear completely opposing things (indeed, I hear sometimes totally contradictory things from good sources (which, by the way, is a big reason you don’t hear me doing too much sourced reporting of my own on Lester – I don’t think it would actually benefit you (all I really know for sure is that the Cubs are very serious about trying to get Lester – full stop))).
  • Patrick Mooney writes about the Ryan Dempster/Jon Lester connection, and about how willing the Cubs will be – or not – to stretch beyond $150 million.



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