Three burning questions the Padres must answer heading into the Winter Meetings

The 2025 Winter Meetings are officially right in front of us; all 30 teams are set to meet in Orlando, Florida, to discuss trades, free agency, and other aspects of team management.

It is also worth noting that the Padres have done nothing to start the offseason, aside from re-signing southpaw Kyle Hart to a one-year deal. The team also saw their ace, Dylan Cease, sign a seven-year, $210 million contract with the World Series runner-up Toronto Blue Jays.

The Padres, as we all know, have a lot on their plate, with tons of their big-name players from 2025 sitting on the open market. Their entire right side of the infield could vanish in the blink of an eye, and their starting rotation is an absolute shambles.

This team cannot shy away from making big moves this offseason, and they must address the following three questions during the winter meetings.

3 pressing questions the Padres can’t dodge at the Winter Meetings

How will the Padres improve the starting rotation? 

By far the biggest need for the Padres this offseason, and president of baseball operations, A.J. Preller, knows it. While the team will retain Nick Pivetta, who was their best and most consistent starter, there are gaping holes in the other four rotation spots.

Cease is already gone, King is likely to leave as well, and Yu Darvish will miss the entirety of 2026 recovering from Tommy John Surgery.

Luckily for Preller, this is one of the deepest free agent classes for starting pitching that we have seen for a minute. Names such as Framber Valdez, Ranger Suárez, Zac Gallen, Michael King, and Merrill Kelly headline the class. It’s not only domestic pitchers, but the international class has a stud of their own in Tatsuya Imai, who may clear all the top starting pitchers already on the market.

The farm system is non-existent for San Diego; the time is now. If the Padres want any chance of contending in 2026, they need to make one or two moves for starting pitching. Luckily for Preller, this is the offseason to do it.

Who will be the first baseman in 2026?

This topic, we feel, doesn’t get much attention, as Luis Arráez and Ryan O’Hearn are both unrestricted free agents. With the Padres making it clear that they are prioritising starting pitching, it makes you wonder how aggressive they are going to be on re-signing one of these two, because it definitely won’t be both.

The truth is, the Padres could realistically let both walk. The reason this is a feasible option is that the team has Jake Cronenworth, who has experience at first base. Moving him from second base, where he currently plays, back to a position he’s familiar with would not be a terrible decision.

If this were the case, Preller would need to survey the trade market for a second baseman, perhaps Brendan Donovan from St. Louis, a team that is looking to sell off some of their players with trade value.

Or if the Padres would like, they could make a trade for Willson Contreras, who is open to waving the no-trade clause in his contract.

There are multiple paths that the front office could follow when it comes to first base, but it is something that needs to be resolved quickly, as the market is way more thin than that of starting pitching.

Should A.J. Preller target a second catcher?

In the first half of 2025, the Padres unarguably had the worst catching tandem in all of baseball, with Elías Díaz and Martín Maldonado combining to be 30% worse than the league average hitter. Having these two at the back-end of the lineup for 162 games would have been costly. That’s why the team traded for Kansas City’s Freddy Fermin, who was a much better bat than either of the two that they previously had.

However, Fermin is by no means an everyday catcher, and definitely not a guy that should start every ⅔ or ¾ games. That’s why it would be wise for Preller to bring in another catcher to not replace Fermin, but to complement him.

One guy that should definitely be on the Padres’ radar is Adley Rutschman of the Baltimore Orioles, as the team may try to move him this offseason.

Rutschman is one of those players who could benefit from a change of scenery, as 2025 was his worst season as a pro by far. Slashing .220/.307/.366, the 27-year-old has only gotten worse since finishing second in rookie of the year voting in 2022.

Not to mention the fact that Baltimore extended their young catching prospect, Samuel Basallo, after only four games in the major leagues.

The Padres would also have an easy in on Rutschman, as former manager Mike Shildt was hired by the Orioles as an upper-level coordinator. This move just makes too much sense for both parties, and it would be a wise move for Preller to make.

Heading into the winter meetings, the Padres need to address starting pitching; everyone knows that. They also know that figuring out the future are first/second base is just as important. Lastly, going for a catcher is an under-the-radar move that could improve this roster big time, and it will be interesting to see how Preller views it.

The 2025 Winter Meetings kick off on Dec. 7.