Clayton Kershaw, in his postgame presser after Sunday night’s World Series loss to the Boston Red Sox, told reporters that he had three days to think about whether he would opt out of the remainder of his seven-year, $215 million contract. It seems like a no-brainer that he would opt out, right? Most would think that one of the best pitchers of the current generation—I have previously referred to him as the greatest pitcher of all-time (click to read more)—should certainly opt out of his contract in an effort to get more money on the open market.

Unfortunately for Kershaw, it’s not that simple. There is a high demand for pitching this upcoming offseason, but Kershaw may not be able to secure the monster contracts that Max Scherzer, David Price, and Jon Lester have gotten in recent years.

For starters, Kershaw will be 31 on Opening Day. That’s not a death sentence for pitchers, particularly elite ones, but it’s not great news for Clayton Kershaw. We’ve seen pitchers like Justin Verlander, Randy Johnson, Greg Maddux, and others maintain success into their mid-to-late thirties. Yes, the latter two players are enshrined in Cooperstown and the former is nearly a lock for the Hall, but there’s no reason that Kershaw can’t be in that conversation.

On the other hand, pitchers like Johan Santana, Brad Radke, and Erik Bedard have flamed out after crossing that age-thirty threshold. These are all cherry-picked examples, but the point is that Kershaw being on the wrong side of thirty does not necessarily mean that his career is over.

It will likely go downhill from here, though, and the reason isn’t his age. It’s his injury history.

Kershaw has had back issues in his career (though he says they are no longer a problem), and he has missed significant time in each of the past three seasons due to various other injuries. From 2010-2015, Kershaw averaged just over 222 innings pitched per season. In the three seasons since, he has averaged fewer than 162 innings, meaning he has not thrown enough innings, on average, to qualify for the ERA title. Of the past three years, he has qualified for the ERA crown in just 2017. He led the majors in ERA that year, of course, but that’s beside the point. Kershaw is looking like a mortal.

From 2011-2014, Kershaw led the majors in ERA, strikeouts, WHIP, FIP, xFIP, and fWAR, and was fourth in innings pitched. He was unconscious. Since then, he’s still leading the majors in most of those categories, but his engine is starting to slow down. The fact that Kershaw is averaging nearly 5.0 fWAR per season over the past three seasons, which have been injury-riddled, is absolutely insane. I’m not trying to argue that he isn’t still one of the premier pitchers in the game—he is—but the time away from the mound is going to start to come back to hurt him eventually.

This is a lazy comparison, I know, but Clayton Kershaw and Sandy Koufax are not too dissimilar. Sandy Koufax was a left-handed pitcher for the Dodgers that was a generational talent. Clayton Kershaw is a left-handed pitcher for the Dodgers (for at least the next couple of days) and is a generational talent. Koufax’s career was cut short due to injury. Kershaw’s career isn’t over quite yet, but the injury bug is starting to hit him. I’m not saying Kershaw has just one year left, but the final bow may be coming sooner than people may think.

So that brings us back to the question: should Kershaw opt out? Logic says yes. An elite pitcher, even one that is thirty-one years of age, will command a large sum of money on the open market. Any offer that Kershaw signs, in terms of overall value, will be greater than the $70+ million he is owed over the next two years.

The problem is that, in terms of average annual value, it’s pretty unlikely Kershaw gets as much in free agency as he is owed under the terms of his current contract. There’s a chance that Kershaw will be able to come away with something like a three-year, $100 million dollar deal this offseason, but I find it extremely unlikely that any team commits more than four or five years with perhaps a team option year tacked on to the end of the contract. Especially given that teams are shying away from spending in free agency in general (check out this article I wrote during the last offseason for more), Kershaw’s odds for a deal longer than five years in free agency do not look great. He’ll definitely be able to get more than the two years he has left on his current contract, but his average annual value will likely not be as high if he opts out.

For the record, Jay Jaffe of Fangraphs completely disagrees with me, but I really think he is underrating the effect that Kershaw’s injuries (and uninspiring playoff performance, to a lesser degree) will have on his earning potential.

We also have to keep in mind that Kershaw, despite his ridiculous pitching ability, is just another normal guy. He has a family and kids who have grown up in Los Angeles their entire lives and moving the family across the country to New York, for example, just to chase a ring might not be in the cards. The Dodgers have the cap space to pay Kershaw even if he opts out, but he might not opt out for the simple fact that he’s guaranteed over $70 million over the next two years. That’s a lot of money for a family of four hundred let alone a family of four.

So all of that leaves us with a pretty mixed bag. I think Kershaw will test the waters of free agency, but it’s nearly a foregone conclusion that he sticks with the Dodgers even if he opts out. If he doesn’t opt out, it wouldn’t come as a complete shock, but Kershaw opting out is certainly not the expected outcome, at least in my view.

Regardless, the Dodgers can’t afford to lose the face of their franchise, and I can’t imagine that winning six straight NL West titles is doing much to hurt the team’s odds of re-signing him should he opt out. Expect Kershaw to opt out within the coming days but look for him to re-sign with the Dodgers during the offseason.

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