What Should Clayton Kershaw Do About His Future?

As he prepares to make one of the biggest contractual decisions of his career, Clayton Kershaw must consider a number of factors with his career pushing into his 30s.

Time comes for all of us, even for Clayton Kershaw, the best pitcher of his generation, the pitcher who finished outside of the top 20 in NL MVP voting only once from 2011 to 2017. Though the lefthander only turned 30 in March, the Kershaw we saw in 2018 was not the Kershaw of previous years, not even the Kershaw of the recent past.

His average fastball was clocked at 90.9 mph (he had averaged 93.1 mph in 2016), and he threw the pitch a career-low 41% of the time. His diminished stuff and new approach resulted in more contact—he registered swinging strikes on only 11% of the pitches he threw. Even though he missed roughly as much time with injuries in 2016 and 2017 as he did in 2018, batters swung and missed on 15 percent of his pitches in 2016 and on 14 percent in 2017. From 2015 to 2017, only 26% of the balls put in play against him were hard-hit; in 2018, that number climbed to 35%.

In any other offseason, this would be a matter for Kershaw and his coaches to spend all winter thinking about—studying extreme slow-motion video and biomechanical data, working on a changeup, anything to ease the transition that has tripped up many greats before him.

But exactly how his offseason plays out depends on a decision he must make before 4:00 p.m. ET on Friday: Will he opt out of the last two years and $65 million of his contract and become a free agent? Or will he leave the market untested and stay a Dodger? Kershaw signed a seven-year, $215 million extension before the 2014 season that included a player option (an “opt-out”) covering 2019 and 2020, years six and seven of the deal. Both sides agreed Wednesday to extend the opt-out deadline two days to Friday afternoon.

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The opt-out, a common leverage-maximizing wrinkle in players’ deals, has not historically led to particularly agonizing decisions. Generally, the price for a top player heads only one direction, and opt-outs position a player to cash in on improving market conditions provided he hasn’t fallen off. Alex Rodriguez opted out of the last three years of his 10-year, $252 million deal during (memorably) the 2007 World Series; because he was coming off an MVP season at 31 and had not yet been tarnished by steroid allegations, he figured he’d score a raise and additional guaranteed years. He wound up getting that deal from those very same Yankees he left, signing a new 10-year, $275 million deal six weeks later. Sometimes, though, players decline, and it’s not worth it for them to test the market. The eight-year, $184 million deal Jason Heyward signed with the Cubs before 2016 included opt-outs for this offseason and the following one. Since coming to Chicago, though, Heyward’s career has tanked—he’s no longer a league-average hitter. There’s no way he opts out of the deal.

Kershaw’s position is trickier. For one thing, the market has softened for all but the very best free agents, sure-thing five- or six-WAR players. He’s not that anymore; he’s declining. But he’s declining from a height few pitchers ever reach, and there’s no real way of knowing the pace at which his decline will proceed. He’s regarded as one of the game’s most exacting workers, so he’s not likely to fall off a cliff. (Metaphorically. Or literally.) At the same time, though, given how much he values his routines, it’s hard to imagine him radically overhauling his training regimen.

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He’s already, though, in the process of overhauling his approach against hitters to counterbalance his body’s decline. Among pitchers who threw at least 160 innings this year, only the Brewers’ Jhoulys Chacin threw a higher percentage of sliders than Kershaw’s 42%. In Game 2 of this year’s NLDS against Atlanta, which was his first postseason start, and a very good one, Kershaw actually threw more sliders than fastballs. Though he struck out only three batters, he had Braves’ hitters off-balance all night—he looked like a lefthanded Greg Maddux, working eight scoreless innings in just 85 pitches. He wasn’t quite so efficient the rest of the postseason, with a 4.20 ERA overall in 22 innings (four starts, one relief appearance), but his transformation is clearly underway.

Teams must now try to figure out where he’ll be three or four years into that transformation. If he opted out, he would presumably be seeking a five or six-year deal, albeit one with an annual salary smaller than the one he’s currently making. (I assume he wouldn’t want a deal much shorter than that; if he did, he’d probably be better served trying to extract one from the Dodgers. Even if he opts out, that may yet be the resolution.)

What would be the price for his services in an open market? Kershaw’s onetime teammate, Zack Greinke, hit free agency at age 32 after the 2015 season—he opted out of the last three years of his Dodger deal—and landed a six-year, $206.5 million contract in Arizona. Greinke, though, was coming off a phenomenal walk year, and such a haul is probably out of reach for Kershaw given his back problems and his waning stuff. (Not to mention: the guys who gave Greinke that contract were fired after that season.) Five years and $130 million, or six years and $145 million, is a more reasonable forecast for his market.

If that’s the ballpark Kershaw and his agent are mulling on Wednesday night, does it move them? It might; he could double the money he’s guaranteed to be paid despite the creep of age and injury, no small thing. Should it? I’m in no position to know what Kershaw and his family want for his future. But $65 million is itself a hefty total, and provided he transitions well into a finesse pitcher, there will still be plenty of demand for his services after 2020. Maybe he’ll bet on himself! And, hey, if the unthinkable happens, and his body fails entirely, there are worse fates in life than being a Dodger lefty legend whose career fate ended far too soon. He can ask the guy in the front row at Dodger Stadium.