The Cubs Front Office Really Knocked It Out of the Park with the Jon Lester Signing

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The Cubs Front Office Really Knocked It Out of the Park with the Jon Lester Signing

Chicago Cubs

High-end free agency is almost always a losing proposition in one way or another. The “winning” bidder tends to be the team that topped all other bidders, and thus already put themselves behind the 8-ball in recouping value. The free agents tend to be around 30 years old, with long contracts that necessarily play out over the course of the player’s natural decline.

Done properly, a good high-end free agent signing provides you with the bulk of its “value” in the early years of the deal. And then, even on good deals, you kinda just have to eat the end.

Although this past offseason’s free agent class was among the weakest in recent memory, especially on the high end, the two offseasons that preceded it were both very strong. It’s not entirely a coincidence, then, that the Chicago Cubs – clearly on the upswing by the second half of 2014 – spent aggressively in both offseasons. Although the pre-2016 class has, so far, been a mixed bag, we have only one season to review and ponder. There’s only so much one season can tell you. What if Jason Heyward really does bounce back in 2017, as history suggests he probably will? The analysis of his signing will change dramatically.

That’s not to say that two years is some magical volume of data by which we can finally analyze a group of signings, but it is, by definition, 100% more information than we have after only one year.

I offer that as a precursor to a great read at FanGraphs on the free agent class of 2014-15, and which contracts now look very different from the day they were signed.

It’s funny to think back to when the Cubs signed Jon Lester – a pitcher over the age of 30 – to a six-year, $155 million contract. It was a monster at the time, tens of millions more than the Red Sox (who knew him better than the Red Sox?) were willing to commit, and one of the largest free agent contracts ever given to a pitcher. Do you remember what you thought at the time?

For me, I thought Lester was an excellent target for where the Cubs were at the time, and, while I felt it was an enormous financial risk to tie up that much money in any pitcher, it was one that the Cubs increasingly had the financial wherewithal to take on. Even then, though, I certainly wouldn’t have said I expected Lester to net 9.3 WAR over the first two years of the deal. After all, he’d been worth 9.1 WAR over the two years before 2015, and that included his career year in 2014. His contract, by the analyses at FanGraphs at the time, was a slight loser.

Of course, most monster free agent contracts are losers in terms of their overall value. As I said in the intro, that’s simply the nature of high-end free agency. For most deals like that, you hope that you get the best production from the player in the early years of the deal, which, in turn, hopefully align with a team’s competitive window.

Given the 9.3 WAR Lester has been worth in his two years with the Cubs, years in which the team reached the NLCS and then won the World Series, I’d say check-check-check-FREAKING-CHECK.

The FanGraphs analysis of the contract now yields a clear winner, both because of changes in the market and changes in projections for Lester thanks to his 2015-16 performance. What’s funny about that is that the contract now projects to be a good value deal to the Cubs even if you ignore the first two years.

That is to say, if the Cubs signed Lester, now 33, today to a four-year contract worth the $105ish million left on his deal, that would be a good contract! Given that the Cubs already got the highest and best value from the deal in the first two years, anything hereafter is gravy. And the projections say it’s going to be tasty, tasty gravy.

So, then: good on the Cubs’ front office for pulling off the rare trick of knocking a big-money free agent contract out of the park, and good on Jon Lester for continuing to dominate on into his 30s.

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.