The Padres Offseason Playbook: Three Key Questions Answered as the Winter Meetings Commence

On Saturday, I posed a few questions I had regarding the Padres entering the 2025 Winter Meetings in Dallas. Most executives have left following today’s Rule 5 draft so now’s a good time to look back at those questions:

Question 1: Will the Padres talk with Roki Sasaki this week?

Answer: no

Sasaki was not there at the Winter Meetings. According to Kevin Acee, the 23-year-old was on his way to the United States from Japan on Tuesday.

Sasaki’s agent, Joel Wolfe. told the media he expects to meet with his client in the coming days and begin hosting meetings with clubs as soon as next week. Sasaki will then return to Japan for the holidays and then have a second round of meetings in America with a smaller list of suitors.

I’d expect Sasaki to visit Petco Park in January.

Question 2: Is this going to be a quiet week for Preller on the free agent front?

Answer: yes

As expected, the Padres weren’t in on any of the big free agents. It’s still pretty early in the offseason and the lower-tier free agents aren’t going to sign until the bigger guys go off the board. There needs to be more clarity in the market before the Padres go do something.

Question 3: Will there be a surprise trade?

Answer: no

There was a big trade, as the Red Sox acquired Garrett Crochet from the White Sox, but the Padres were never going to acquire him after giving up their top pitching prospects last season and not wanting to surrender Ethan Salas or Leo De Vries.

There was a ton of talk around the availability of Dylan Cease though and that should only continue since the free agent prices of starters seem to be out of some teams’ comfort zones. Cease has one more year of control and the Padres are looking to increase their financial flexibility (sound familar?) so that they can build out their roster.

Jon Morosi connected the Orioles to Cease today.

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