What’s at stake if Clayton Kershaw opts out of his contract with the Dodgers

LOS ANGELES — Clayton Kershaw and the Los Angeles Dodgers agreed on Wednesday to extend his deadline to decide whether to opt out of his contract to Friday at 4 p.m. ET, the team announced.

Kershaw signed a seven-year, $215 million deal before the 2014 season, and has $65 million remaining on the contract. Kershaw is set to earn $32 million in 2019 and $33 million in 2020. The left-hander originally had three days after the World Series to make his choice, ending at midnight ET Wednesday night, before the two sides agreed to extend the deadline.

Kershaw pitched and lost in Game 5 of the World Series on Sunday night, clinching the championship for the Red Sox. He allowed nine runs in 11 innings in his two starts against Boston, losing twice. After the series Kershaw said he hadn’t yet made up his mind.

“I haven’t made the decision yet,” Kershaw said. “We have three days to talk, between us and the Dodgers, and see what happens.”

Now, it turns out, they will have five total days to talk, after the extension.

Kershaw has as impressive a resume as any active pitcher in baseball, a seven-time All-Star with three Cy Young Awards (2011, 2013, 2014), an MVP (2014) and has finished in the top five in Cy Young voting in four other years. His 2.39 ERA is the lowest among starting pitcher in the live ball era, which dates back to 1920.

All of his 316 career starts and 11 major league seasons have come with the Dodgers, who drafted Kershaw with the seventh overall pick out of Highland Park High School in Texas in 2006.

“Clayton is the Dodgers. He’s the heart and soul of this organization,” pitcher Rich Hill said Sunday night. “He’s a guy who’s put it on the line for so many years and has had so much success as a Dodger. I just hope they do the right thing.”

Manager Dave Roberts when addressing the Dodgers after Sunday’s World Series loss mentioned Kershaw by name and praised his legacy with the franchise.

“What he’s done for the organization, the fan base, wearing this jersey, Clayton exemplifies what it is to be a Dodger and to be a man of character,” Roberts said.

Kershaw opting out wouldn’t necessarily end his tenure with the Dodgers, and the deadline extension suggests the two sides are trying to work out an extension or re-working of his current contract this week.

Dodgers president of baseball operations Andrew Friedman and general manager Farhan Zaidi have said numerous times this season that they want Kershaw to remain with the Dodgers, and that can still get done. If he opts out, it will have to happen through free agency, with other teams able to bid for his services.

What’s likely next, if the Dodgers can’t work out a new deal with Kershaw in the next two days they will almost certainly extend him the qualifying offer, a one-year, $17.9 million deal — the average of the top 125 salaries in baseball — that if Kershaw declines would bring the Dodgers draft pick compensation should he sign elsewhere this winter.

The deadline to extend the qualifying offer is 5 p.m. ET on Friday, the same time that Major League Baseball’s quiet period ends, meaning any free agent is free to sign with any new team starting Friday evening. A player can sign with his former team at any time before Friday.

Pitching by nature is fraught with risk, and there are plenty of red flags with Kershaw, who has reached 30 starts just once in the last five years. Kershaw over the last three seasons averaged just under 25 starts per year and missed time with a back injury in all three years.

Kershaw’s disabled list stints:

In 2018 we saw the effects of years of toil finally provide tangibly different results for Kershaw, whose fastball dropped to 91.31 mph, two miles slower than his career norms, making it less distinguishable compared to his slider. Opposing batters hit .291 with a .508 slugging percentage against Kershaw’s fastball in 2018, compared to hitting just .237 with a .359 slugging percentage versus the pitch for the previous five seasons.

Kershaw posted his worst ERA (2.73) in nine years and his worst FIP (3.19), worst OPS against (.630) and worst strikeout rate (23.9%) in 10 years, which makes this in many ways an odd time to hit the free agent market.

The flip side of that is those numbers — even while underwhelming compared to Kershaw’s standard of excellence — are still quite strong relative to the rest of the league.

The only pitcher contract with a higher average annual value than the $32.5 million per year that Kershaw is walking away from belongs to Zack Greinke, whose six-year, $206.5 million deal signed three years ago with the Diamondbacks averages $34.4 million annually.

But this maneuver for Kershaw would be less about maximizing his salary for the next two years, but rather for the next four or five seasons, if not longer.

Eleven pitchers have signed contracts in the last five years with an average annual value of at least $20 million, including Kershaw’s deal he signed in 2014. Only two of those contracts were signed in the last two offseasons, when baseball’s free agent market dried up relative to recent times.

That said, this year’s free agent class is much more robust than last year, with Kershaw potentially joining fellow headliners Bryce Harper and Manny Machado. Add in that the Dodgers and Yankees will presumably be involved in the deep end of the free agent pool after opting for relative austerity in 2018 by staying under the competitive balance tax threshold to resent their luxury tax to a lower, less punitive rate.

Kershaw was ranked third in Grant Brisbee’s free agent rankings this offseason, behind only Machado and Harper.

In other words there is money to be had this offseason, and Kershaw is better poised to hit the market now heading into his age-31 season rather than wait two years, when at 33 he would be older than any of the pitchers who signed those lucrative deals.