jon lester feature red soxAlthough at times it felt like an Obsessive Watch already (with updates here, here, here, here, and here), I refused to pull the trigger on an Obsessive Jon Lester Watch until the offseason arrived. Indeed, it would have been my preference to wait until the actual offseason arrived (i.e., when transactions can actually take place after the World Series), but the smoke is too billowy and the player too important.

So, here we are.

Lester, who starts tonight for the Oakland A’s in the AL Wild Card Game against the Kansas City Royals, is likely to be one of the most hotly-pursued free agents this Winter, and it’s fairly plain at this point that the Cubs will be involved in that process. It would be unwise to label the Cubs a “favorite” at this point, though there are some obvious factors that militate toward the Cubs: they’ve got the strong need, they’ve got the money, they’ve got an attractive team (finally), and they’ve got the front office connection.

As for Lester, he’s not ready to speculate on free agency while he’s trying to do the playoff thing, but he does speak openly about what lies ahead in this WEEI piece. A little bit of what Lester had to say:





I came out here knowing what I am. I’m a two-month rental and hopefully I can somehow help win a World Series for the Oakland A’s. It eases a lot of the questioning of the ‘What are you going to do?’ Everybody knows it’s two months and then probably not sign a contract with the Oakland A’s …. [T]hen once everything [in the playoffs] is said and done I can sit down with [agent] Seth [Levinson] and my family and we can evaluate. Then we can start getting into the excitement of free agency and all the possibilities and what-ifs and wondering what’s going to happen. That stuff will come when it’s time and when we get there, yeah, I’m sure it will be an exciting time.

You can read WEEI’s piece for more from, and on, Lester.

On the year, Lester posted a 2.46 ERA over 219.2 innings between Boston and Oakland. His 2.80 FIP was the best of his career, and his 3.10 xFIP was also sterling. At 6.1 WAR, Lester was tied as the fourth most valuable pitcher in baseball (just ahead of fellow free agent arm, Max Scherzer, who was at 5.6 WAR), and was generally dominant from start to finish this season. He picked a good time to put together that kind of season.

Since he was traded midseason, Lester will not be eligible for a qualifying offer, and thus will not be tied to draft pick compensation. That will make him all the more attractive to some of the biggest market clubs, particularly those who otherwise stand to lose a first round pick when pursuing guys like Max Scherzer or James Shields.

How crazy will the Lester bidding get? Well, I can envision his side asking for something in the range of the six-year, $144 million extension Cole Hamels got from the Phillies a couple years ago (just before he reached free agency, so it didn’t include any arbitration years), although Hamels was two years younger then than Lester is now.



If we do some back-of-the-napkin valuation calculations, starting Lester at 5.0 WAR in 2015, and dropping him 0.5 WAR for each year thereafter, he could be worth $30 million in 2015 (using $6 million per free agent win), $27 million in 2016, $24 million in 2017, $21 million in 2018, $18 million in 2019, and $15 million in 2020. That’s $135 million over six years, though that’s obviously a very rough estimate (starting at 5.0 WAR in 2015 might be aggressive, given that his three marks before this season were 4.3, 3.2, and 3.5).

At the low end, there is no chance Lester’s market will not exceed (perhaps dramatically) $20 million per year and five years. So, bump each of those figures north a few million and a year or two, and that’s probably the range we’re looking at. The Cubs have the money to make that work, and they know that sometimes you have to “lose” on the valuation calculation to actually get the guy you want.

Will they do it this time around? We’ll find out in the coming months.

Oh, and just for fun, Nick Cafardo is stirring things up:




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