The Dodgers lost another World Series and could lose Clayton Kershaw, others during pivotal offseason

The Los Angeles Dodgers lost their second World Series in a row on Sunday, dropping this year’s Fall Classic in five games to the Boston Red Sox. That the Dodgers won the National League pennant after an uneven regular season won’t matter. Nor will it matter that the Dodgers underperformed their run differential by a majors-leading 10 games. The takeaway will be that the talent was there — it always seems to be — and yet the Dodgers again failed to win a ring.

Now, the Dodgers enter what’s certain to be a pivotal offseason. If Clayton Kershaw opts out of his contract — he has two seasons worth nearly $70 million remaining — he would join Manny Machado, Yasmani Grandal, Hyun-Jin Ryu, Brian Dozier, Ryan Madson, and John Axford as free agents. (David Freese could also be a free agent, depending on whether his $6 million option gets exercised.) That list includes four of their top 12 performers, per Wins Above Replacement.

In a sense, the Dodgers have been preparing for this winter for a while. Cot’s Contracts, a website that tracks baseball finances as best as any out there, suggests the Dodgers shed nearly $50 million from Opening Day payrolls between 2017 and 2018. The same site estimates the Dodgers were able to remain under the tax threshold, resetting their overage penalties.

Presumably, the plan is to now go back to spending more than $200 million on payroll. The Dodgers might not have a choice, really. They’ll need to figure out how to keep Kershaw in town, and they’ll likely sign or trade for new starters at second base and catcher. Their bullpen could use some help, and it wouldn’t be too surprising if they sign a veteran starter as well. Inking the injured Garrett Richards to a one-year deal with a club option while he rehabs from Tommy John surgery would a vintage Andrew Friedman move.

But if the Dodgers want to go above and beyond, what might that look like? Would they make a run at keeping Machado and figuring out how to play him alongside a healthy Corey Seager? What about swinging for the fences for Bryce Harper? Might they pursue A.J. Pollock with an eye on shifting Chris Taylor to fill the aforementioned second-base void? Landing another top-end starter, a la Patrick Corbin, would make sense too — though Friedman will likely be reluctant to tie up too much salary in two starting pitchers.

The Dodgers have options — lots of them. The question remains the same as it has been for the past winters: Can they find the right combination to bring home their first World Series championship since 1988? And if not, then what happens next?

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