Los Angeles Dodgers franchise lefty Clayton Kershaw originally had a 11:59 p.m. ET deadline Wednesday to decide whether he'd exercise the opt-out in his contract and become a free agent. One alternative would be to pass on the opt-out and to remain under the two years and $65 million or so left on his contract. The third option would be to work out an extension with the Dodgers that replaces those final two years. That may be what's in the works ...
The Dodgers and Clayton Kershaw have agreed to extend the deadline on his option decision until Friday at 4 p.m. ET.— Los Angeles Dodgers (@Dodgers) November 1, 2018
"I haven't made the decision yet," Kershaw said when asked about the opt-out following Sunday's loss in Game 5 of the World Series. "We have three days to talk, between us and the Dodgers, see what happens. And then we'll go from there ... I think we'll have some conversations, for sure."
It appears those conversations are indeed happening, and this mutual agreement to extend the negotiating window would seem to increase the chances that Kershaw remains a Dodger.
Kershaw, 31 in March, threw 161 1/3 innings with a 2.73 ERA (142 ERA+) and 155 strikeouts this season, which is obviously excellent. It also qualifies as his worst season in nearly a decade. Kershaw hasn't posted an ERA or an ERA+ that high since finishing the 2010 season with a 2.91 ERA (133 ERA+) in 204 1/3 innings.
Furthermore, Kershaw has failed throw more than 175 innings in each of the last three seasons, mostly due to back problems, after throwing at least 195 innings every year 2010-15. His strikeout-to-walk ratio remains very good but has slipped from 15.6 in 2016 to 6.7 in 2017 to 5.3 in 2018, and his fastball velocity is beginning to trend down:
Between the regular season and postseason Kershaw has thrown over 2,200 big-league innings in his career. Among pitchers who started their careers this century, only CC Sabathia, Felix Hernandez and Mark Buehrle threw more innings before their age 31 season than Kershaw. Velocity loss and wear-and-tear is inevitable. It happens to every pitcher.
For Kershaw, the question is not whether he can get a higher average annual value the next two years. The question is whether he can get a larger total guarantee than $65 million. Teams are smart, they know they're probably not getting peak Kershaw, but even this slightly diminished version of Kershaw is really good. Getting more guaranteed money seems possible.
With the opt out deadline looming, the CBS Sports scribes got together to talk out Kershaw's opt-out situation. Should he opt out? Will he opt out? And why? Here is everyone's response.
Katherine Acquavella: Yes, I think Kershaw is going to opt out. If what happened with Zack Greinke in 2015 is any sign, there's a good chance a team out there will pay Kershaw more than the $70 million that the Dodgers owe. Also worth noting that Greinke and Kershaw have the same agency (Excel Sports) and the same agent (Casey Close). Kershaw has dealt with injuries in each of his last three seasons, and his playoff struggles don't match up with his regular season totals but there are plenty of teams out there that could sign him. He'd be an automatic upgrade for most teams.
R.J. Anderson: I believe Kershaw will and should opt out. It makes the most sense for him from a leverage perspective assuming his desire is to extend his deal beyond two years. Is this strategy likely to land a new deal that will beat his AAV over the next two seasons? Probably not. But I do think he could land a longer deal that guarantees him more money overall. I go back and forth on whether Kershaw returns. My guess is that Andrew Friedman would be fine letting him walk -- because of the risk factor with any pitcher, let alone one with declining velocity and an achy back. My guess is also that Dodgers ownership would be less-fine with letting him walk, and that Kershaw returns on a three- or four-year pact.
Mike Axisa: I think Kershaw should opt out. This is likely his last chance at a monster payday. I don't think he'll have much trouble securing (much) more guaranteed money in free agency than the $65 million remaining on his current contract. That said, my hunch is the two sides will work out an extension before the deadline, perhaps something like an additional two years and $70 million on top of his current deal.
Even at this point of his career, where we can start to see signs of decline, Kershaw is still plenty good enough to front the rotation of a contender, and he and his agent would be foolish not to leverage that opt-out into more money. I do think Kershaw wants to remain a Dodger the rest of his career and the Dodgers know keeping Kershaw improves their chances of bringing home a title. That's why I think an extension is the most likely outcome. If push comes to shove though, I think he'll opt out and test the market, with the Yankees and Astros the super early favorites to get involved in the bidding.
Jonah Keri: I do believe Clayton Kershaw will opt out. Even if he's truly a Dodgers loyalist, opting out enables him to negotiate a new deal that could bind him to L.A. through his mid-30s. And of course if he wants to see what's out there, no time like the present. Kershaw can still befuddle opponents with his array of breaking pitches and his often brilliant command. But he throws closer to 91 than 95 these days, he's no longer the best pitcher in baseball, and there's a little Felix Hernandez in his career path right now. If he doesn't test the market now, he might never again see a mega-payday ... his Koufaxian track record be damned.
Dayn Perry: Yes, I'll say Kershaw will opt out, and I'll say that the Dodgers allow him to walk. He'll do better on the open market than $70 million, but I don't think he'll wind up with the biggest contract among free agent pitchers this offseason (I'll say Patrick Corbin takes that honor). Thanks to his aforementioned deep repertoire and command-and-control skills, Kershaw projects to be a useful to very good starting pitcher for the near- to mid-term. That assumes he's generally healthy, and frankly that's a large assumption these days. I'll get even more specific and say that Kershaw winds up signing with his home-state Astros after they opt to let Dallas Keuchel go elsewhere.
Matt Snyder: I think he's going to opt out. He won't be able to come close to $35 million AAV on the open market, but he will get a deal longer than three years and worth well more than $70 million. Maybe something like five years and $100M with an opt-out after two years in case he becomes CLAYTON FREAKING KERSHAW again?
I'm going to agree with Dayn that I think the Dodgers just decide it's OK for an amicable split. The Astros make sense, especially with what they've done for some other pitchers after acquiring them. Also, be on the lookout for the Phillies if they don't land both Manny Machado and Bryce Harper (and I can't see them getting both).