For the first time in three years, the Dodgers’ winter has begun with a quiet period.

They didn’t reach the World Series this fall. Which means they have some time to sit back and take stock of their roster before the offseason kicks into gear.

This year, of course, uncertainty surrounds the future of the sport. A lockout is almost certain to commence at the beginning of December. When a new CBA is struck, and what changes to the league’s financial structure it could possibly entail, is still anyone’s guess.

Because of that, forecasting the Dodgers’ moves this winter also remains a guessing game. At what will be a potential point of transition for the franchise, there are any number of routes that president of baseball operations Andrew Friedman and Co. could take.

For now, though, they do begin the offseason with a few obvious questions that will need to be answered.

Here are the five most pressing, as the two-time defending champions try to move on from their failed three-peat bid:

Tarik Skubal a Dodger again?

This year’s free agent class is as thin as any in recent memory. But Skubal represents the one, superstar-caliber, potential record-setting exception.

The two-time Cy Young Award winner is expected to break Yoshinobu Yamamoto’s high mark of $325 million guaranteed for a pitcher. He could get upward of $400 million –– if not even closer to $500 million –– if the right combination of suitors emerges.

The Dodgers, of course, will be in the mix.

Their admiration for Skubal was clear at the trade deadline. Their appreciation for his talent and work ethic only grew during his three months with the club. The relationships he built in the clubhouse –– including, first and foremost, with Blake Snell –– figure to only strengthen their case, as well.

However…

The Dodgers already have ample future financial commitments. How comfortable they are adding another, especially before knowing what changes will come with MLB’s new CBA, could be the defining question of their winter.

Entering the offseason, their 2027 payroll (for luxury tax purposes) is at $388.4 million, according to Cot’s Baseball Contracts. Even for 2028, there is over $300 million on their books at this point.

If the league were to enact a salary cap, or harsher luxury tax rules (this year’s first tax threshold was at $244 million), those totals could prove problematic.

And even if not, that would still be a lot of long-term money tied up in 30-something-year-old players (Shohei Ohtani, Mookie Betts, Will Smith, and Yoshinobu Yamamoto are all under contract for at least half-a-decade more).

That isn’t to say the Dodgers can’t afford, or won’t be comfortable with, a mega-signing for Skubal. If they feel he maximizes their World Series odds for even the next couple seasons –– in the way they thought he did this past year –– they will make an effort to sign him.

At this point, though, too many uncertainties surround his market, the sport’s larger landscape, and the Dodgers’ preferred economic plan, to know exactly where they stand in his sweepstakes.

Re-sign Kiké Hernández?

Each of the last three offseasons, Kiké Hernández has been a free agent.

Each of the last three winters, his ultimate re-signing felt like a fait accompli.

This time, however, even Hernández seemed more uncertain about his chances of staying in Los Angeles in 2027. 

After the team’s NLCS elimination, he said he “would love to be back” but didn’t “really know what’s going to happen” –– so much so, he added, that “if I’m not, I hope that I get to play for a winning team [somewhere else].”

In an Instagram post a few days later, he expressed his gratitude to the organization and its fan base with a foreboding “If this is it for us…” caveat.

What makes Hernández’s situation interesting this year is what it could reveal about the front office’s bigger-picture roster-building philosophy. In re-signing the October hero and veteran utilityman the last few seasons, the club was making an effort to keep its core –– even including part-time fringe players like him –– together.

But now, it’s possible a large shake-up could be in order. If so, the 35-year-old Hernández would figure to be a potential casualty. 

“We had a good run, but here we are,” he said. “I don’t know what’s going to happen with me personally, moving forward for next year. But this team is well-positioned to keep winning.”

Trade Teoscar Hernández?

Last winter, the Dodgers at least entertained potential trade discussions involving outfielder Teoscar Hernández.

This winter, it would be no surprise if they were even more open to shopping the veteran outfielder.

For all Hernández has done in his three years as a Dodger, after all, he could be the first core piece squeezed out in their transition to the future.

The club has a wave of corner outfield depth at the top of their farm system, starting with rookie sensation Josue De Paula. They have few other veteran pieces who would make sense to explore moving. And if the team was looking for ways to get younger, and open up opportunities for its top prospects, Hernández (who is entering the final year of his contract anyway) would be the logical place to start.

That doesn’t mean the Dodgers are determined to move him. When fully healthy, he has still looked like an impact player. And given De Paula’s massive defensive question marks in the outfield, it’s not as if they have a risk-free replacement waiting in the wings.

But, Hernández could nonetheless be in a tenuous place this offseason. 

Whether or not the Dodgers stick with him will be another illustration of their larger priorities entering 2027.

Bring back “Bullpen Dawgs?”

Another key decision for the Dodgers will come in the bullpen, where their three (actually, four) longest-tenured arms are all out of contract.

Blake Treinen, Alex Vesia and Evan Phillips are all entering free agency, after playing key roles in the team’s back-to-back World Series titles. So too is Brusdar Graterol, who hasn’t pitched since the 2024 Fall Classic because of shoulder and back injuries.

It all raises a familiar question: Will the Dodgers try to maintain some level of continuity, specifically by attempting to re-sign Vesia and/or Phillips? (Treinen’s future is less clear, at 38 years old and coming off a season-ending shoulder injury, as is Graterol’s given his daunting injury history).

Or, will they see this as another chance to cycle some fresh faces onto the roster, while potentially opening up a couple relief roles for some of their younger arms?

Strike an extension?

There are two primary contract extension candidates for the Dodgers this offseason –– one on either side of the age spectrum, and representing different possibilities for the club’s future.

Andy Pages is the first, coming off an All-Star campaign in 2026 and entering his first season of arbitration eligibility in 2027. Both sides are likely to at least be open to exploring a potential longer-term commitment this offseason. Doing so would lock down the one young core member of the Dodgers’ lineup –– Pages is currently on track to be the only sub-30 member of the starting lineup next year –– and give them one future pillar to build around.

Then there is Freddie Freeman, whose contract situation will come to a head over the next 12 months.

The 2027 season is the final one of Freeman’s current deal. However, the 37-year-old has indicated a desire to potentially play at least two more seasons beyond it, putting the onus on the Dodgers to make a decision on his future in Los Angeles.

To this point, the future Hall of Fame first baseman has repeatedly sidestepped any contract talk publicly. But it’s unlikely next year begins without him and the team at least discussing his long-term status in the organization at some point.

It could be yet another barometer of how the Dodgers view their own long-term plans overall. 

This season felt like the beginning of the end for their dynasty core. And while many of their most familiar faces will still be back in 2027, this winter should offer indications of how quickly the club plans to transition into a new era, and how aggressively they will begin maneuvering to get there.