2025 MLB Winter Meetings Preview: High Stakes, Big Names, and the A’s Roster Puzzle

Baseball’s offseason is about to hit full throttle as the 2025 MLB Winter Meetings descend on Orlando this weekend. If the General Manager Meetings are the appetizer, think of the Winter Meetings as the main course – where deals get done, rumors heat up, and the baseball world converges to shape the upcoming season. With only six of MLB’s top 25 free agents signed, the stage is set for a flurry of negotiations, surprise trades, and major roster shakeups.

So far, it’s been a relatively quiet offseason. Just two headline-worthy trades have gone down – one between the Mets and Rangers, and another involving the Orioles and Angels.

But that calm is unlikely to last. With so many impact players still on the board and every front office in the same building, the expectation is that this week could be the tipping point for a wave of movement across the league.

Rule 5 Draft Looms Large

One of the more under-the-radar but crucial events of the Winter Meetings is the Rule 5 Draft, scheduled for Wednesday, December 10. For front offices, it’s a delicate balancing act – deciding which prospects to protect on the 40-man roster and which to risk exposing to other teams.

The Oakland A’s have already made a few key decisions on that front. They added right-handed pitcher Braden Nett, currently ranked as the organization’s No. 4 prospect, and international signee Chen Zhong-Ao Zhuang to the 40-man roster.

That move shields them from being plucked by other clubs in the draft. But not everyone made the cut.

Three other top-30 A’s prospects – catcher Daniel Susac (No. 11), right-hander Kenya Huggins (No. 23), and third baseman Brennan Milone (No. 26) – were left off the protected list, making them eligible to be drafted by other teams. It’s a gamble, and one that could come back to bite if any of those players break out elsewhere.

A’s Offseason Strategy: Depth First, Arms Next?

So far, Oakland’s approach to the offseason has been all about building out depth. But the expectation is that they’ll soon turn their attention to bolstering the pitching staff – both in the rotation and at the back end of the bullpen. There’s a clear need for high-quality arms, and with the market starting to move, the Winter Meetings could be the moment the A’s front office makes its move.

There’s also buzz around potential contract extensions for some of the team’s younger hitters. Locking in core talent before arbitration years or free agency is a strategy that’s paid off for other clubs, and the A’s may look to follow suit if the right opportunities arise.

Labor Uncertainty in the Background

One cloud hanging over the proceedings is the looming possibility of a work stoppage in 2027. While it’s still two years away, the uncertainty around future labor negotiations is something every front office has to consider – particularly when it comes to long-term deals and big-money commitments.

That said, the consensus around the league right now is that teams aren’t letting that uncertainty slow them down. Whether that’s optimism or just posturing remains to be seen, but this week should give us our first real sense of how much that looming deadline is influencing decision-making behind closed doors.

What to Watch

The official Winter Meetings run from December 8 through December 11, and if history is any guide, we’re in for a few whirlwind days. Expect trade talks to heat up, free agent dominoes to start falling, and the Rule 5 Draft to bring a few surprises. For the A’s, it’s a chance to retool, reinforce, and maybe even lock in some foundational pieces for the future.

One thing’s for sure – the hot stove is about to get a whole lot hotter.