This story was excerpted from Juan Toribio’s Dodgers Beat newsletter. To read the full newsletter, click here. And subscribe to get it regularly in your inbox.

As president of baseball operations Andrew Friedman and general manager Brandon Gomes sat at the podium following a second consecutive National League Division Series exit in the postseason, they made sure to state that the ultimate result this season was an “organizational failure.”

It’s a sentiment the Dodgers also shared after the ‘22 season. Over last winter, the Dodgers stayed consistent with their message that they would be relatively quiet over the offseason in order to give some of their young players an opportunity to play more. 

This winter, after falling short following another 100-win season, the Dodgers are expected to be very active in both the free agent and trade markets. What exactly do the Dodgers have to accomplish this winter? Let’s look at five questions the Dodgers must answer over the next couple of months. 

Can they improve the starting pitching?

The Dodgers’ offense picked the worst possible time to go cold for three games during the NLDS against the D-backs, but they also never really got a chance to get downhill and establish themselves with a lead. 

That’s because the Dodgers’ starting pitching was historically bad in the NLDS. Clayton Kershaw allowed six runs and recorded one out in Game 1. Bobby Miller wasn’t much better in Game 2. And then there was Lance Lynn, who was giving up homers every chance he got. 

Some of the issues the Dodgers had last season were out of their control. Tony Gonsolin and Dustin May both needed Tommy John surgery and Julio Urías, the team’s Opening Day starter, was placed on paid administrative leave after getting arrested on domestic violence charges. 

Still, for the Dodgers to make another run at a World Series, the starting pitching needs an overhaul. Miller and Walker Buehler are the two certainties in the rotation. Ryan Pepiot might’ve shown enough to secure a spot, too. Emmet Sheehan and Gavin Stone also have a lot of potential. 

But with a lot of strong options in the free-agent market, the Dodgers will need to be heavily in the mix for Blake Snell, Yoshinobu Yamamoto, Jordan Montgomery and Aaron Nola, among others. In the trade market, Corbin Burnes might become available, and the same applies for Tyler Glasnow if the Rays decide to move on from their ace. 

All of that will become clearer after the World Series and when teams can make contact with these players. But you can almost guarantee that the Dodgers will be heavily involved. They’ll just have to deliver. 

“We'll certainly be focused on starting pitching, for sure,” Friedman said. “And it's how to balance the young guys and where we're at there.”

Will Kershaw be back in 2024?

This question goes hand in hand with the search for starting pitching. Kershaw was compromised by a left shoulder injury last season and wasn’t sharp in the postseason. He’s now a free agent. His decision will ultimately come down to health and if he feels he can still contribute at a high level. 

If both of those answers are a yes for Kershaw, then he could be back in a Dodgers uniform next season, helping the rotation. If those aren’t the answers, however, the future of the likely first-ballot Hall of Famer becomes a little more unclear. 

Do they improve the position player side? 

Mookie Betts, Freddie Freeman and Will Smith will surely be hitting atop the Dodgers’ lineup next season. But with J.D. Martinez, David Peralta, Jason Heyward, Amed Rosario and Kiké Hernandez all being free agents, the Dodgers have some holes to fill this winter. 

Gavin Lux should be back next season, which should give the Dodgers a boost. Miguel Vargas, who struggled as a rookie, should also get another opportunity to earn a job next spring. Miguel Rojas shined as a defender in ‘23, but the Dodgers could, once again, pursue upgrading at the position. 

In the outfield, the Dodgers could also use some more help. Peralta and Heyward were solid this season, but they were role players and were exposed some during the postseason. The issue, however, is that the free-agent market for position players is very thin this winter.

What will they do with Muncy’s option?

Max Muncy has been a big part of the Dodgers’ over the last five seasons and the team will have a decision on his $10 million club option. Given Muncy’s rebound year at the plate, it’s hard to see the Dodgers not picking up the option even if the former All-Star did struggle defensively, especially late in the season. 

How about the Ohtani sweepstakes?

Well, this is the question everyone wants to know heading into the winter. Two-way superstar Shohei Ohtani will be the biggest free agent, maybe ever, this offseason and just about every team with the financial means will be involved for his services. The Dodgers will be right in the thick of it.

The complication, of course, is that Ohtani won’t pitch in 2024 and despite what his camp says, there are some concerns about what he might look like coming off second major elbow surgery when he does return to the mound in ‘25. If his pitching is compromised in any way, is it practical to spend half a billion dollars on a designated hitter? That’s what teams will have to figure out this winter. 

On the field, there’s no denying Ohtani makes any team better. He’s ticketed to his second AL MVP next month and is still one of the most feared hitters in the Majors. Pairing him with Betts and Freeman for at least the next four seasons will be frightening. Now, the Dodgers won’t be alone in their pursuit of Ohtani. The Mets, Yankees, Red Sox, Mariners, Cubs, Angels and others will be involved. It’ll just be a matter of what Ohtani wants to do.

“Obviously, we can’t talk about free agents or impending free agents,” Friedman said. “But from our standpoint, which has been our mindset and the great fortune our ownership has provided us to be aggressive, to go out and put the best team on the field that we can. And for us, obviously, we’re extremely angry, disappointed with how these last two offseasons have gone, and we’re going to do everything we can to put ourselves in position for it not to happen next year.”