Will Red Sox ace Chris Sale live up to his contract extension?

The ink on Chris Sale’s five-year $145 million dollar is barely dry, but it’s never too early to dive into some early takes.

Chris Sale has been the most dominant starting pitcher to don a Boston Red Sox uniform that I’ve ever had the pleasure of watching. He’s only been in Boston for two years but the man has already accumulated 13.7 fWAR and 545 strikeouts against just 77 walks. He’s finished top five on the Cy Young ballot in each of the last five seasons and he would’ve certainly won the award last year if it weren’t for a late season injury. And he still hasn’t reached his 30th birthday.

With this in mind it is not at all shocking that the Red Sox were eager to ink the southpaw to an extension before he entered his walk year and they’ve done just that with a five-year $145 million contract. Many Red Sox fans – including myself – rejoiced with the knowledge that we will have the privilege of watching Sale take the mound every fifth day for the foreseeable future. A more complex question, however, is how likely he is to live up to that hefty price tag?

Pitchers on the wrong side of 30 and long term contracts go together like toothpaste and orange juice. You have the disastrous contracts like those given to Mike Hampton, Kevin Brown, A.J. Burnett, Barry Zito, and C.C. Sabathia (the 2nd time). You have contracts that started out well but aged poorly like those given to Johan Santana, Felix Hernandez, and Jered Weaver. But sprinkled in you have a few slam dunk successes like the deals given to Max Scherzer (to date), Cliff Lee, and C.C. Sabathia (the first time).

It turns out that predicting how pitchers over the age of 30 will perform long term is (surprise!) very hard. In fact, team’s with entire departments whose job it is to run cost benefit analyses that I would imagine are far more sophisticated than mine struggle to do a good job predicting pitcher performance. So I’m not going to pretend I can do a better job in this article. Instead, I’m going to lay out the framework of this debate.

The Good

Let’s start with length. This deal is only five years. Anyone who thought a 30-year old Chris Sale on the open market would command less than seven years is stuck in a pipe dream. Getting Sale for the rest of his prime while only taking on two seasons that I would think are likely to be sub-optimal is pretty fantastic. In fact, it’s not at all hard to believe that a 34 or 35-year old Sale is getting outs. And, in all likelihood, if Sale pitches well he’s going to exercise that third year opt out anyway and we will never see an age 34 Sale in a Red Sox uniform.

As I mentioned above, Sale is one of, if not, the best pitchers in baseball. In fact, I’ve written before that Sale has enjoyed more success by age 30 than all but a handful of pitchers. What I did not talk about in that piece was how greatness under thirty translated to results after 30. Below I have compiled a list of all starting pitchers who averaged more than 4.5 fWAR per 200 innings pitched with a minimum of 600 innings tossed starting at the end of the Dead-ball Era (1920) .

* denotes player is active and hasn’t reached their age-35 season to date.

Sale ranks unbelievably well by fWAR per 200 IP. Only Roger Clemens, Clayton Kershaw, and old friend Pedro Martinez can claim to have been more dominant in the first halves of their career by this metric. The takeaway here seems to be that dominance before 30 is a pretty good indicator of dominance after 30. It’s too early to judge Kershaw, but every other pitcher who toppled 5.0 fWAR per 200 innings in the early half of their career were reasonably good in the latter half. Everyone in that group maintained a FIP- below 90, a K/BB of 2.98 or better, and averaged 4.75 fWAR per 200 innings between age 30-35. By the crude $9 million/WAR metric, Oswalt’s accumulated $144 million value would be the lowest of those pitchers over that age span. Including this season, which was not part of the extension, Sale will make $160 million over the next six years so basically all of those pitchers would’ve been worth the deal.

Things get dicier in the 4.5 fWAR-5 fWAR per 200 innings range. There are a good amount of Felix Hernandez, Dwight Gooden, Brandon Webb, and Erik Hansen level failures. There are also players like Justin Verlander, Roy Halladay, Greg Maddux, Tom Seaver, Fergie Jenkins, and Bert Blyleven that posted a second act of their career worthy of a Cooperstown plaque. I imagine that at the time it was very hard to tell who would age like Doc Gooden and who would age like Doc Halladay. And the risk with pitchers of any talent level is huge given how frequently injuries derail older pitchers. However, the hit rate of players in the above table is extremely high. Out of the 17 players who have retired or pitched through age 35, 12 would have been worth $100 million by the $9 million/WAR criteria. Without any numbers in front of me, I will confidently say a fair bit more than 5/17 $100 million contracts in the MLB are complete albatrosses so this is about as safe a bet as you’re going to get.

The Bad

His opening day start? Obviously, I’m kidding. The biggest knock on this contract for me personally – besides the inherent unavoidable risk of injury – is the opt-out after 2022. Opt outs are about as far from team friendly as any contract clause you can cook up and it’s amazing to me how frequently players are getting them thrown into contracts these days. Obviously, for Sale that was never going to be a deal breaker, but it’s still sub-optimal. Consider what is, in my opinion, the most likely scenario: Sale is utterly dominant over the next four years just like he has been over the last six years. The Red Sox would happily take a chance on him for the next two or three years at the current going rate but instead he opts out and gets paid $30 million for the next four years (which I would imagine the Sox would not do).

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That last bit was obviously worthless speculation, but it’s a scenario that happens all the time with opt outs (see Martinez, J.D. 2020). The other option is no better. Sale gets hurt and the Red Sox overpay a pitcher who knows he would have no shot at making $30 million on the open market. Basically opt outs make it so that if a team is smart, they don’t get rewarded for finding players that age well and if a team blunders, they are hamstrung. For that reason, I’m always a fan of an extra year over an opt-out on elite players (though that may not have been the two options on the table).

However, complaining about Sale’s opt-out is rather nit-picky. Overall, I think his deal is very team friendly and is much kinder long term than I would’ve expected. I’ll spare you all two paragraphs of talking about injury risk as that applies to literally every pitcher who signs a long term contract in the history of ever. Unless a pitcher has significant prior injury risk (Sale doesn’t) it’s barely worth copy and pasting that bit from every piece I’ve written on similar topics.

All in all, I really like this deal. Had Sale hit the open market, seven years at $230 is probably about where I would’ve pegged him assuming he is dominant as usual this season. I certainly think he looks like a better pitcher than David Price did at a similar age when Dombrowski gave him 7 years at $217 million (which, by the way, I was hardly upset about). There’s risk in this deal as there is in any mega-contract, but if you’re going to spend money, this is the type of deal you bet on.