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Come Fan with UsTuesday, June 23, 2026

Clayton Kershaw, Cy Young winner and $300 million man

Jeff Gross

Clayton Kershaw is going to win the Cy Young Award on Wednesday. He’s also the best pitcher alive, and he’s a free agent after next season. He pitches for the Los Angeles Dodgers, This is, to nick the title from a famous George Clooney movie, a “Batman & Robin.” It’s going to cost hundreds of millions of dollars, and there will be unexplainable iron nipples on the uni …

Wait, no, it’s the perfect storm. The perfect storm. This pitcher, in this market, at this time in his career, for this team. They’re talking about a $300 million deal. Are you even surprised? It seems logical at this point.

But there’s also the quiet pragmatism of a soon-to-be tycoon. Kershaw is … curious.

“I think any player, that’s the reward of baseball, to make it to (free agency),” Kershaw said. “I think any player gets curious when you get close, for sure.”

Curious is a good way to put it. Because the question before you is this:

How much money would it take for the Dodgers to let Kershaw sign with another team?

It’s an honest question. Pretend there was a rival team, “The Goliaths,” and they were just bought by the multi-billionaire who invented tacos. He wants Kershaw. He won’t shut up about Kershaw. He drives his staff crazy about Kershaw. Wears a foam hat in the shape of Kershaw. And when free agency hits, he personally calls Kershaw and offers $500 million.

Do the Dodgers match that? A contract for $50 million a year? Part of me thinks they might, if only because the spend-spend-spend strategy is about more than buying the best players. It’s a team reclaiming an identity. It’s a team taking over the Evil Empire identity right when the Yankees started worrying about the luxury tax. And part of that brand is the idea that the Dodgers have more money than anyone else. Having more money than anyone else means keeping the best pitcher alive when you get the chance.

But what about $600 million? Or $700 million? People buy a lot of tacos, you know, and the Goliaths aren’t shy. At some point, the Dodgers would ungracefully bow out.

It’s an interesting thought experiment. Maybe the Dodgers wouldn’t budge over $300 million, or maybe they would get into a tinkling match up to a billion dollars because they’re the Dodgers, dammit.

What if, what if, what if. Except that’s going to stay a thought experiment because the Goliaths don’t exist. Now think of the team that would take a risk on Clayton Kershaw for $300 million -- that’s the equivalent of two Masahiro Tanakas, four or five Matt Garzas, or 300 Edinson Volqui.

Yankees wouldn’t do it, not if they’re still serious about avoiding the luxury tax. Red Sox can spend, but not like that. The Giants probably wouldn’t go for $175 million, much less $300 million.

Run through the list of all 30 teams and see which ones are primed to go crazy for Kershaw. There’s one. And it’s the same team you figured he was going to sign with before starting the first paragraph of the article. The Dodgers are bidding against themselves. The spending on Puig, Ethier, Ryu, Grienke, League, Gonzalez, Crawford, and Beckett was all done by a team completely aware that Kershaw was approaching free agency. And Kershaw was completely aware of what the Dodgers were doing. Both sides were patient enough to wait for right now.

Maybe a better thought exercise would be to ask what Kershaw would get if the Dodgers didn’t exist. He’s younger than Verlander was when he signed was essentially a seven-year, $180 million deal. He’s younger than Felix Hernandez, who signed for the equivalent of seven years and $175 million. He’s also pitching at a higher level than either of those pitchers, though not by much.

Someone would make him the first $200 million pitcher. Pick a rich team. One of them would blink. Ten years, $250 million wouldn’t be that far-fetched, considering that’s close to the annual value of Verlander’s deal.

Whatever the ceiling you came up with in that second thought experiment -- and I think $250 million is teetering between realistic and insane -- is Kershaw’s market value. So the equation is something like this:

(Kershaw's eventual contract) - market price = The I Guess You Caught Us Being Spendy With Everyone Else tax

The Dodgers can’t lowball Kershaw. They can’t claim they’re poor because all of the other contracts. So the Dodgers will give him a deal that will flabbergast you. We knew the extension was inevitable. Now we know it will be record-setting. And the record will probably stand for a long time. Ain’t nothin’ coming around like this for a while.

For more on the Dodgers and Clayton Kershaw, please visit True Blue LA.

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