Clayton Kershaw Can Turn Big Year into Record-Setting $250M Free-Agent Megadeal

Among the accomplishments Clayton Kershaw can achieve in 2018 is becoming the richest pitcher in Major League Baseball history for the second time.

The first time he did it was when he inked a seven-year, $215 million contract extension with the Los Angeles Dodgers in January 2014. Although David Price surpassed that when he signed with the Boston Red Sox for seven years and $217 million in December 2015, Kershaw might soon reclaim the record.

The left-hander's "seven-year" pact with the Dodgers was really a five-year deal with a two-year option. He can either stay in Los Angeles in 2019 and 2020 for $65 million total, or he can opt out after 2018 and chase greater riches as a free agent.

The three-time National League Cy Young Award winner and one-time National League MVP hasn't yet made a decision regarding his opt-out. But rest assured, he knows it's there.

"I think the great thing about having options is just that, it's an option," said Kershaw, who'll turn 30 on March 19, per Tim Brown of Yahoo Sports. "It's not really a decision. So, I think for me it's just go out and try and pitch and be healthy and then if I have options at the end of the year, great."

How much could Kershaw be worth as a free agent? Oh, say about $250 start.

Three pitchers have found contracts worth north of $200 million in free agency in the years since Kershaw signed his record-setting deal. Price's takes the prize for overall value, while Zack Greinke's six-year, $206.5 million deal with the Arizona Diamondbacks takes it for average annual value at $34.4 million per year. Then there's Max Scherzer's seven-year, $210 million contract with the Washington Nationals.

Kershaw hasn't even reached free agency, yet his wins above replacement confirm that he's already a far more valuable pitcher than any of those three were when they hit the open market:

Player Span Career WAR
Clayton Kershaw 2008-2017 57.4
Zack Greinke 2004-2015 48.6
David Price 2008-2015 29.2
Max Scherzer 2008-2014 24.0


Of course, what Kershaw has done isn't amazing just in comparison to his peers.

Only five pitchers —Tom Seaver, Bert Blyleven, Roger Clemens, Christy Mathewson and Walter Johnson—have ever accumulated more WAR through the age of 29 than Kershaw has. He also owns a 161 adjusted ERA+, the highest of any pitcher who's ever logged over 1,900 innings.

Anyway, you get the point. Kershaw's great, and he deserves a free-agent contract that would match Price's and Scherzer's in length and beat Greinke's average annual value. Do the rough math, and $250 million comes out as the most logical bar to clear.

This is assuming, however, that Kershaw doesn't slip into his darkest timeline in 2018.

The chief concern is his health. In recent years, few young starters have had to handle as many innings as he has. That could explain the back problems that limited him to 27 starts in 2014, 21 starts in 2016 and 27 starts in 2017. 

Not everything was hunky-dory when Kershaw pitched last season. He did his usual thing of collecting way more strikeouts (202) than walks (30) in his 175 innings, but his home run rate skyrocketed to a career-high 1.2 per nine innings.

The long ball plagued Kershaw into October, when he served up eight homers in six appearances. That set a new record for a single postseason and put yet another black mark on his October track record.

It's only fair to acknowledge that the postseason is a dangerous beast that's humbled many a great pitcher. But out of the 26 hurlers who've logged at least 100 postseason innings, none has anything close to the 1.99-point gap between Kershaw's 2.36 regular-season ERA and 4.35 postseason ERA:

And yet, every reason to be concerned about Kershaw's 2018 fate comes with a reason for optimism.

His recent back injuries have succeeded in taking him off the mound but not so much in restricting his dominance. Since 2014, he leads all pitchers who've logged at least 100 starts with his 1.99 ERA, his 8.0 strikeout-to-walk ratio and his .531 OPS allowed.

In the meantime, Kershaw's arm and shoulder are doing fine. That shows not just in the clean injury reports for both, but in how his pitch velocities and arm slot are holding relatively steady.

Regarding his home run problem, it's worth pointing out that pretty much everyone ran into the same issue last year. It's also worth pointing out that Kershaw's gopheritis stemmed from an issue that should be correctable. As FanGraphsJeff Sullivan pointed out, he was simply making it too easy for batters to sit on low pitches. 

Lastly, there's the reality that Kershaw's overall postseason performance doesn't tell the whole story.

He's made a handful of brilliant starts—most recently a dazzling seven-inning, 11-strikeout performance in Game 1 of the 2017 World Series—here and there that prove he's not entirely incapable of conquering October. All he needs to do is string a few together.

Rather than the year it all falls apart, 2018 may well be the year that it all comes together for Kershaw. He could thus head into free agency with an extraordinary track record and with helium from a career-defining season.

Just as important, he shouldn't have to worry about the same forces that have flattened the earning powers of many of this winter's top free agents.

The luxury-tax threshold will increase from $197 million for 2018 to $206 million for 2019. That will give Major League Baseball's top spenders extra breathing room. Some of them are preparing for it ahead of time by aiming to get under the tax threshold for 2018, which would reset the penalties they'll have to pay when they go back over.

That list includes the Dodgers, who would surely love to have Kershaw back if he opts out. The New York Yankees and San Francisco Giants, either of whom could look to lure Kershaw away from Los Angeles, are two more.

The Red Sox and Nationals project to be over the tax in 2018, but they can gain breathing room after the year by saying goodbye to in-house free agents. For the Nationals, that's Bryce Harper, Daniel Murphy, Gio Gonzalez and Matt Wieters. For the Red Sox, it's Drew Pomeranz and potentially Price, who has his own opt-out.

With teams like these in the mix, it's not hard to imagine the bidding for Kershaw shooting beyond $250 million and closer to $300 million. A seven-year deal at $40 million per year would come out to $280 million.

To see just how high he can go, Kershaw needs only to address all the doubts in 2018.

Oh, and also opt out.


Stats courtesy of, FanGraphs and Brooks Baseball.  

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