Jon Lester Decision Could Head into Wednesday, Offers May Have Reached $150 Million

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Jon Lester Decision Could Head into Wednesday, Offers May Have Reached $150 Million

Chicago Cubs

jon lester feature red soxYesterday’s relative Jon Lester bombshell was the report from Ken Rosenthal that, “barring a late change,” the lefty would be choosing between the San Francisco Giants and the Chicago Cubs. Although Lester’s agents scrambled quickly to douse that report by adamantly stating that other teams are still involved, by the end of the evening’s updates, there was tentatively a positive tone about the Cubs’ chances to get Lester – something that seemed a bit of a stretch just a few hours earlier. Such is the nature of these things.

We’ll see if that mood changes throughout the course of the day, during which Lester will finally pick his team, as reported yesterday.


Well, about that.

Each of Buster Olney and Rob Bradford report that Lester’s decision process could spill over into Wednesday. Why the delay? Well, it sounds like it’s a pretty simple explanation: the offers are climbing rapidly, and ownerships are getting involved because of the huge amount of dollars at stake. As Olney puts it, there’s a competitive piece to this, too:

According to both Buster Olney and Ken Rosenthal, Lester now has multiple offers in the six-year, $150 million range. Moreover, Rosenthal specifies that all of the Cubs, Giants, Red Sox and Dodgers are at least in that range (which would be surprising – and possibly troubling – with respect to the Red Sox), and one of the teams has indicated a willingness to go to seven years and $175 million.

Interestingly, Rosenthal’s piece notes that Lester still may not go to the highest bidder, preferring instead to go where he’s most comfortable. *And* Rosenthal’s piece reiterates his earlier report that, barring a change, Lester is choosing between the Cubs and the Giants. Read those two things together, and, in my considered opinion, you can probably figure out which team has suggested a willingness to go to 7/$175M. Here’s a hint:

It’s totally the Dodgers. And I’m starting to think that’s not really where Lester wants to go, regardless of the money.

I know it’s easy to get impatient with this, and I know that you won’t conjure any sympathy given that Lester is about to be rich dozens of millions of times over, but try to put yourself in Lester’s shoes and think about how difficult this decision must be. Gordon Edes does a nice job summing up the non-monetary aspects of this decision for Lester, and why it’s so tough. So many different angles pulling at him, and it’s not like he’s choosing for a year or two. He’s choosing for what might be the rest of his playing career.

But, back to the money.

For weeks now, this has always seemed where this race would end up: multiple teams right there at that 6/$150M level, and each deciding whether they want to be the one to blink and go over the top, or if they want to rest on the strong offer and their sales pitch. If one blinks, they can’t know that another team won’t also blink, and then the bidding climbs to yet another tier.

And it’s easy to say, “if you’re at $150 million, what difference is $160 million?” You say that a few times, and suddenly, you’re at $200 million, and you’ve lost all sense of grounding. As I’ve said before, I am comfortable with the Cubs going to something like six years and $155 million, while including a seventh year team and/or vesting option (for which the buyout is that extra $5 million there in the guarantee). That strikes me as an “overpay” in terms of valuation, but sometimes you’ve got to overpay to get the guy. Beyond that overpay, however, I’m not sure it’s the right move for the Cubs to go any higher, given the many other options out there.

The Cubs do have a financial advantage, by the way, with respect to their state income tax, which is already much lower than in California, and is scheduled to fall to a fair bit below Massachusetts on January 1. Athletes pay state income tax where it is earned – there’s a complicated process of reconciling what you owe based on where your games are played and where you train in the spring – but, long story short, the Cubs have an advantage here that could amount to as much as $10 million or so over the course of a six-year, $150 million contract. Let’s hope Lester’s agents are making that tax distinction very clear.

Lastly for this update, a guess from Phil Rogers, who is talking to folks behind the scenes:

That’s just one guess, folks. So take it only for what it’s worth.

It already seems like today will be another crazy day, so strap in and follow along. I’ll do my best to help you flatten out the emotional peaks and valleys.

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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.