Nov. 2: With the deadline now just over three hours away, Ken Rosenthal of The Athletic tweets that both sides are “optimistic” about reaching a new agreement. As Rosenthal points out, an extension prior to 4pm ET isn’t required for Kershaw to remain in L.A. into 2019 and beyond. Even after what seems to be a surefire opt-out, he could continue negotiating with the Dodgers, although other teams would then formally be allowed to pursue Kershaw as well.

Oct. 31: The Dodgers announced tonight that they’ve agreed to push back the deadline on Clayton Kershaw’s opt-out decision until Friday afternoon at 4pm ET. The original agreement in his contract was that he’d have three days after the end of the World Series, meaning a decision would have been due tonight. Kershaw has two years and $65MM remaining on his contract but has the right to opt out and enter the free-agent market.

There’s been persistent speculation that the two sides would simply reach an agreement to extend Kershaw’s current contract by a year or two, and it’s possible the extension of the deadline window was agreed upon with that very outcome in mind. Kershaw’s opt-out provision comes toward the end of what was at the time a record-setting seven-year, $210MM deal — the largest ever for a pitcher when he put pen to paper. (David Price has since topped that sum with a seven-year, $217MM deal.)

It’s long seemed logical that if an extension can’t be worked out, Kershaw would be able to earn more than that $65MM sum by opting out and testing free agency. While he’s spent time on the DL in each of the past three seasons, primarily due to back issues, he’s remained among the game’s most talented arms when healthy enough to take the field. And for all the talk about his durability since his initial back injury in 2016, Kershaw has averaged 25 starts and 162 innings per season (191 innings per season when factoring in the playoffs).

Kershaw, 30, has notched a ridiculous 2.26 ERA in that three-year stretch, and while he had a “down” season in 2018 by his Cooperstownian standards, he still pitched to a terrific 2.73 ERA with a sensational 155-to-29 K/BB ratio in 161 1/3 innings of work. Even a somewhat diminished Kershaw is among the most talented pitchers on the planet and would figure to command well in excess of $65MM in total on a free-agent contract. Perhaps that’d come with a lesser average annual value, but certainly in terms of overall contract value, his earning power outpaces the remainder of his contract.

Friday marks the formal end of the exclusive negotiating window that teams have with their own impending free agents. Even if Kershaw had opted out tonight, then, he would only have been able to further talk with the Dodgers for the next two days. Viewed through that lens, it’s somewhat natural to delay the deadline, as the only team he’d have been talking to for the next 48 hours is the Dodgers. Still, it’s easy to view this as a show of good faith from both sides that the two will eventually work something out.