Dodgers: Could Clayton Kershaw retire after the 2021 season?

You’ve been wondering, we’ve been wondering, the baseball world has been wondering. What’s going on with the Los Angeles Dodgers and Clayton Kershaw? The left-hander is slated for free agency after 2021 and it feels bizarre that he’s going into the season without a new contract.

This is different from last time, too. Kershaw had an opt-out clause that he exercised before the two sides agreed to a three-year, $93 million extension. Now, there’s nothing. And the Dodgers just made a blockbuster move by bringing in starter Trevor Bauer and haven’t addressed Kershaw’s situation.

And when you add Kershaw’s recent comments into the mix, you can’t help but think retirement could be on the horizon for the soon-to-be 33-year-old, especially after he finally captured that elusive World Series in 2020.

When asked by Jorge Castillo of the Los Angeles Times about a new contract with the Dodgers, Kershaw replied, “I don’t know. Honestly, I wish I had an answer.”

Oh yeah, and about finally winning that World Series and preparing for 2021?

“I wasn’t as enthused to get back going again [in ’21], which is a good thing. It’s a great problem to have. I think every offseason in the past it’s been, ‘I just want to get this done. I just want to do it, do it, do it.’ And there’s this passion and it just constantly builds and builds and builds.“And now the pressure is just because we have a great team and we’re supposed to win. That’s awesome.”

Yup, one of the best starting rotations we might ever see. But aside from playing for more rings, what does Kershaw have to push him each and every day? He’s got three Cy Young awards, an MVP, five ERA titles, eight All-Star Game appearances, he’s led the NL in strikeouts three times (and all of MLB once), and finally rid himself of those postseason demons.

When you consider he’s been dealing with injuries for the better part of five straight years, you can’t help but think this could potentially be the end of the road for the future Hall of Famer.

It’s not like he’d be ending his career prematurely, either. After 2021, that’ll be 14 MLB seasons, which is more than enough to solidify his place as a baseball icon. And also, when you really think about it, what’s the Dodgers’ reasoning for not extending him by now? He’s a team legend. He deserves whatever he wants, whenever he wants. Could there be some sort of understanding that Kershaw may want to reevaluate things after the year ends? Is Kershaw fine with the team maybe wanting to wait things out? Who knows.

But something does feel off, and it’s certainly not insidious to assume Kershaw could be ready to hang up his cleats and wrap up one of the most successful careers ever as the natural progressions continue to unfold.

Dodgers: Projecting 2021 starting rotation after Trevor Bauer signing

Here's what conventional wisdom would project the Los Angeles Dodgers starting rotation to look like in 2021 after the addition of Trevor Bauer.