The Oakland A’s are headed into the Winter Meetings with something they haven’t had in a while: momentum. After four years of rebuilding - and losing - they finally found a groove in the second half of 2025, playing at a playoff-caliber pace post-All-Star break. Now comes the hard part: turning that late-season spark into a full-season flame.
With the Hot Stove heating up, the A’s find themselves at a crossroads. They’ve got a young core that’s starting to click, a farm system that’s producing real talent, and a front office that knows how to work the margins.
But they’re also operating on a small-market budget and playing in a stadium that doesn’t exactly scream “destination.” So how do they take the next step?
Free Agency: Risk, Reward, and Reality
Let’s start with the obvious - free agency. For a club like Oakland, it’s always a tightrope walk.
If you want to land a quality starter, you’re probably going to have to overpay. That’s how they got Luis Severino, and it might be the only way to bring in another arm this winter.
The problem? Even mid-rotation starters are commanding top-tier money.
Think $67 million for a guy who might be your No. 3.
That’s a tough pill to swallow for a team trying to stretch every dollar.
And then there’s the ballpark factor. Sutter Health Park played like a launching pad in 2025, which doesn’t exactly help the pitch to free agent arms.
Convincing a starter to sign up for that environment might take more than just money - it might take years. That’s where GM David Forst could get creative.
Maybe a three-year deal for someone like Chris Bassitt or a four-year offer to reliever Tyler Rogers gets the conversation started. It’s a gamble, no doubt.
But sometimes, that’s what it takes to find value in a market that rarely favors the underdog.
Trades: Three Paths, One Goal
The trade route offers more flexibility, but it comes with its own set of challenges. There are essentially three types of deals the A’s can make: move established talent, part with top prospects, or work the fringes with smaller, lower-impact moves.
1. Trading Established Talent - Not Likely
The A’s have made it pretty clear that their core hitters aren’t on the block. That includes Brent Rooker, Nick Kurtz, Jacob Wilson, Shea Langeliers, Tyler Soderstrom, and Lawrence Butler.
And that makes sense. These are the guys who helped fuel that strong second half, and they’re young enough to be part of the next good A’s team.
But here’s the rub: those are exactly the types of players other teams want in return for frontline pitching. Think of clubs like Pittsburgh, Kansas City, or Cincinnati - all looking to swap arms for bats. If Oakland won’t part with their core, it limits the kind of deals they can realistically make.
2. Trading Top Prospects - Also Unlikely
The A’s are trying to transition from rebuilding to contending, but they’re not in “all-in” mode just yet. That means their top three prospects - Leo DeVries, Gage Jump, and Jamie Arnold - are likely off the table.
And honestly, they should be. These are potential cornerstone pieces, not trade bait.
That said, there’s still some prospect capital to work with. Braden Nett and Henry Bolte sit just outside the top tier, while Colby Thomas brings that “MLB-ready” appeal. Tommy White still carries value, and guys like Steven Echavarria and Devin Taylor could pique the interest of rebuilding clubs.
But let’s be real - if you’re trying to acquire a No. 2 starter and leading with Colby Thomas instead of DeVries, you’re going to be met with a lot of polite declines. The A’s can make offers, but without dipping into their top shelf, it’s going to be tough to land a difference-maker.
3. Smaller Moves - Not Enough on Their Own
There’s always the option to make minor moves - sign a veteran infielder, add a depth arm, maybe bring in a utility guy. Think Aledmys Díaz, Luis Urías, or even his brother Ramón.
Jace Peterson types. These are the kinds of players who fill out a roster, not transform one.
And while those moves can help at the margins, they won’t move the needle enough to turn Oakland into a true contender. At some point, the A’s need to make at least one bold swing - either in free agency or via trade - if they want to be more than just a feel-good story in 2026.
So What’s the Play?
The safe route is to stay the course. Let DeVries arrive when he’s ready.
Give Jump and Arnold time to develop into rotation anchors. Use 2026 to get a full read on guys like Max Muncy, Zack Gelof, and Denzel Clarke.
Keep stockpiling talent, and don’t force the issue.
But then again… this team just played two months of playoff-caliber baseball. They’ve got a young core that’s starting to gel, a few prospects knocking on the door, and a fanbase that could use a reason to believe. There’s a window here - maybe not wide open, but cracked just enough to sneak through.
If Forst and his front office can thread the needle - make one smart signing, pull off one savvy trade, and avoid mortgaging the future - the A’s could enter 2026 as a legitimate wild card threat. It won’t be easy.
It never is in Oakland. But if the second half of 2025 was a preview of what’s possible, then the A’s might just be closer than we think.
The path is narrow. The margin for error is slim.
But the opportunity? It’s real.