Nathan Eovaldi is a third major extension candidate for the Red Sox

In a normal baseball offseason, we would be at the point of the offseason in which some major free agents remain on the board, but many have already signed. Meanwhile, teams would have just exchanged arbitration figures and started to focus more attention on extensions for their best players. Obviously the lockout is preventing any of that from happening (besides the free agent thing, I suppose, since many signed before the lockout), but front offices are undoubtedly still focusing on all of that. From a Boston Red Sox perspective, most of the outside focus on that front has understandably been around guys like Rafael Devers and Xander Bogaerts.

Nathan Eovaldi doesn’t measure up to those guys in terms of either overall value, consistency, fan recognition, or a number of other categories, but his case for an extension should not be slept on. The righty was the best pitcher on the Red Sox roster all season, garnering some well-earned Cy Young votes at the end of the season. He is also set to hit free agency after this season and could be in line for a big payday next winter if the Red Sox let him get that far.

That, however, doesn’t mean it should be considered a slam dunk for the Red Sox to lock him up long-term. Let’s go through a few of the factors the front office will be taking into consideration ahead of any potential talks for a long-term deal with their de facto ace.

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Health

Although he was able to get through the entire 2021 season, postseason included, without any sort of major injury, Eovaldi’s health is always going to be first and foremost on the mind with regard to a long-term deal. That’s true of every pitcher, of course, and Eovaldi is about to enter his age-32 season. Injuries would be a concern for any pitcher of that age, and his history with arm issues makes the issue all the more complex.

With Eovaldi, we’re talking about a pitcher who has already undergone two Tommy John surgeries, one in high school and another late in the 2016 season. Between the 2015 and 2019 seasons, he failed to reach the 25 appearance mark as well as the 125 inning mark. According to Baseball Prospectus, he has had four trips to the 60-day injured list since 2013.

All of this is to say that there is real risk that Eovaldi could sign a multi-year extension and then immediately suffer a major injury that keeps him out for months, and perhaps even into the following season. Again, injury risk is present for every pitcher, but the saying goes that the best predictor of future injury is past injury, and Eovaldi has plenty of that. On the other hand, he made 32 starts last season and in the shortened 2020 season he just missed a couple of starts due to a lower body injury.

True Talent

Eovaldi is something of an enigma because, even tossing aside his health questions, there is some question as to just how good he actually is on the mound. There is the simplistic view of things to never buy high, and considering Eovaldi is coming off a career year this could certainly be viewed as buying high. The righty finished the 2021 season with 32 starts, putting up a 3.75 ERA and an elite 2.79 FIP. His control at his best is about as pinpoint as it gets for a major-league starter, and his strikeout stuff, while not elite, has still settled in above-average the last few seasons.

I would say his true talent is not the fourth best pitcher in the American League, which according to Cy Young voters he was in 2021. That said, I think he is a legitimate top-of-the-rotation pitcher. Again, we’re just talking when he’s healthy, which is an important distinction to make. We’ve seen lesser versions of Eovaldi on the mound, specifically in 2019, but he never seemed fully healthy in that season. On the contrary, he was obviously great in 2021, and he was also quietly very good in 2020, to say nothing of his now-legendary run in 2018. And on the topic of that season, his postseason run served to make his regular season success that year (of which there was plenty) underrated.

All of that is to say that Eovaldi is a very good pitcher, which isn’t breaking news. No, I would not be going out of my way to pay him like he’s Jacob deGrom or Gerrit Cole, but just thinking about how good he can be expected to be for the next couple of seasons when healthy, expecting All-Star level performance doesn’t seem unfair.

What else do they have?

In thinking about potential extensions, part of the calculus is certainly what is coming up the pipe in terms of possible replacements. It’s less of an issue with a pitcher than a position player since you can obviously use more in a season, but it’s still worth considering. For the Red Sox, Eovaldi is currently joined at the top of the rotation by Chris Sale, who is under contract through the 2024 season with a vesting option for 2025. Sale is a major wildcard right now, though, and while there is reason for optimism it’s impossible to say right now whether or not they can expect him to be a top-of-the-rotation arm for the duration of his contract.

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Looking down the pipeline a little bit, there doesn’t appear to be many options there either. Boston’s farm system is improving at a quick rate, and that is also true of the pitching pipeline in particular, but Boston’s arms on the farm are more mid-rotation or back-of-the-rotation types than potential Eovaldi replacements. Any prospect can break out at any time, and someone like Brayan Bello or Jay Groome (or whoever else you want to pick) could take a big step forward this year and start to emerge as that kind of future option, but they are not there at this point.

To me, the most probable young arm to come up and take that mantle would be Garrett Whitlock, but that is also an open question. Hell, it’s an open question as to whether or not he’ll even be a starter for this season. He’s in a similar category as Sale where we have to see what Whitlock can be as a starter before we can start to really bank on anything.

What’ll it cost?

This is the big question, right? It’s obviously a lot more difficult without knowing what the CBA will look like, which could alter the way teams pay veterans depending on how things shake out. But for our purposes, let’s assume things don’t change much in the way tenured players like Eovaldi are paid. In that case, I think there are actually a few interesting comps from this year’s free agent market, whose deals and recent numbers you can see below.

These are not, to be clear, perfect comparisons. Rarely does such a thing actually exist, and that is especially true for a pitcher like Eovaldi who has an extensive injury history along with a few different arsenals he’s used. We should also mention that all of these pitchers are younger than Eovaldi, Gausman and Stroman by a year and Rodriguez by three. Of these pitchers, I think it’s pretty clear that Gausman is the most valuable, and you can make an argument that Eovaldi is right around the same tier, just based on recent performance, as Stroman, with Rodriguez a step behind.

It’s not quite as simple as just matching contract for mildly similar pitchers, though. For example, I don’t think Eovaldi, who will be entering his age-33 season whenever an extension kicked in as opposed to Gausman and Stroman entering their age-31 seasons and Rodriguez entering his age-29 campaign. Additionally, the three-year sample hurts Eovaldi a bit since it includes a 2019 season in which, as mentioned above, he never really seemed totally healthy. So, I don’t see a five-year deal on the table for Eovaldi. Given the injury history discussed above, too, there is probably something of a discount Eovaldi would have to take if he were to get an extension before throwing a pitch in 2021.

With all of that taken into a consideration, I would think a contract of either three or four years is most likely where the two sides would settle. In terms of average annual value, I’d expect it to be between the marks for the pitchers above, probably skewing towards the higher end, bringing us to a contract somewhere in the 3/60 to 4/88 kind of range.

Given all of that we just discussed, it seems like the move is probably to wait a bit and hope he is willing to discuss an extension mid-season. As you can probably tell from some of the sections above, I am confident in his ability to perform when he’s healthy. It’s just a matter of how healthy the team can keep him, and any more time you can wait on that front the better. But for me, the more important piece that comes from waiting has to do with the pitchers around him. By waiting until midseason, the organization should theoretically have a better idea in what they have in both Chris Sale and potentially the starter version of Garrett Whitlock. Waiting would have the downside of increasing the price towards the high range above, but that’s a price I’d be willing to pay, again, if Eovaldi was willing to discuss a deal midseason.