The stove may be off after Thanksgiving, but the baseball world is just starting to sizzle — and this is exactly when smart front offices can change their future.
You survived the turkey coma, powered through the yams, and even endured the relatives you secretly hoped might skip the trip this year. Now that the dishes are done and the leftovers are dwindling, the real offseason drama begins. A couple of marginal relievers on the transaction log isn’t enough to reset the palate — it’s time for the Hot Stove to actually get hot.
Here’s a fresh look at where the A’s currently stand — and where they arguably should be heading — as the calendar flips to December. And this is the part most people miss: the biggest wins might come from the moves they choose not to make.
Brendan Donovan
On paper, Brendan Donovan checks a ton of boxes the A’s should love. He hits left-handed, gets on base at an impressive clip, and offers capable defense at second base — exactly the type of well-rounded profile that helps stabilize a lineup and infield. For a team trying to climb back toward relevance, that kind of reliability is incredibly appealing.
But here’s where it gets controversial: despite all of that, he might be exactly the type of player the A’s should avoid pursuing right now. The reason has less to do with Donovan himself and more to do with basic supply and demand. Reports suggest that multiple teams are heavily interested in him because of his versatility, solid performance history, and team-friendly years of control as an arbitration-eligible player. When that many suitors line up, the cost almost always spikes.
In other words, instead of landing a sneaky bargain, the “winner” in a Donovan sweepstakes is likely to be the club that surrenders the most talent. That’s a dangerous place for the A’s to be. Donovan is a good everyday contributor, but he’s not the kind of franchise-altering piece you empty a premium prospect bucket for. He’s not “give up Gage Jump” good — and that distinction matters.
For a small- or mid-market team, preserving the farm system is often the only way to sustain success. The A’s can almost certainly find another competent infielder — maybe not with Donovan’s exact blend of skills, but good enough — without surrendering one of their top young arms or high-upside prospects. The safer, smarter path is to let someone else overpay while Oakland targets value in less crowded corners of the market. Do you think a mid-tier everyday player is ever worth sacrificing a potential frontline prospect for?
Sung-Mun Song and Jake Cronenworth
Sung-Mun Song looks like the kind of pitcher who could quietly make a lot of sense for the A’s: a reasonable projected commitment in the three-year, $15 million range, and the upside to solidify part of a rotation or pitching staff without wrecking the budget. That’s exactly the type of deal that can move the needle for a team in Oakland’s position.
However, reports out of Korea suggest that Song may be leaning toward San Diego. If that happens, it doesn’t just close one door — it might open another. If the Padres land Song and already have depth on the right side of the infield, Jake Cronenworth suddenly becomes a very interesting trade target. His shifting role could turn him from lineup fixture into trade chip.
Cronenworth, a veteran who can handle both first and second base, might be viewed by San Diego as more expendable if Luis Arraez walks in free agency and Song joins the rotation or pitching staff. There could still be a fit for both players on the roster, of course, but if the Padres decide Cronenworth is more valuable as a piece to flip than as a mid-power first baseman with a career slugging percentage around .406, the A’s should be ready to pounce. That type of slugging output doesn’t scream long-term solution at first base, but as a second baseman or versatile infielder, it looks a lot more attractive.
From Oakland’s perspective, Cronenworth could quietly solve second base for multiple seasons. He’s under contract through 2030 at an annual salary in the low double-digit millions, which is a manageable number in today’s market for a solid regular. He’ll turn 32 in January, meaning the deal runs through his age-36 season — not without risk, but hardly outrageous for a player whose strengths include skills that traditionally age well, like plate discipline and approach.
Cronenworth checks several boxes that align with what the A’s should be seeking. He’s another left-handed bat and is coming off his best season in terms of on-base percentage, with a walk rate that suggests a strong command of the strike zone. Over his career, he has generally graded out around league average defensively at second base, though his 2025 fielding metrics reportedly dipped. For the A’s to invest, they would need to believe that downturn stems from nagging injuries or random fluctuation rather than real decline.
The fit gets more interesting when you look at the bigger infield picture. Even with a prospect like Leo DeVries arriving, there appears to be enough room across the dirt for bats like Jac Caglianone or similar first-base types (standing in for “Kurtz”), a versatile option like Wilson, DeVries himself, and one more steady everyday regular. Cronenworth doesn’t block the future; he bridges the present to it.
On the Padres’ side, there’s strong incentive to restock the farm system after trading significant prospect capital to Oakland for Mason Miller. At the same time, they’re in win-now mode, so they’d likely seek players who are reasonably close to contributing. A package built around names in the Colby Thomas “help soon” tier or Tommy White “impact later” category could be appealing. If they prefer arms, pitchers in the Mason Barnett, JT Ginn, or Kade Morris range might move the needle.
That’s where the real debate starts. Is it worth giving up a mid-tier but promising prospect for several years of a high-floor, versatile regular like Cronenworth? The argument in favor is strong: he’s cost-controlled, flexible, and fits a clear positional need. From this perspective, sacrificing one prospect from that group looks like a reasonable gamble to stabilize the lineup. Would you pull the trigger on that kind of deal, or is that still too steep for a 30-something infielder without star-level upside?
Free Agent Pitchers
Here’s a frustrating reality: attracting starting pitchers to Oakland is inherently tough. The current ballpark situation feels like a mix between a Triple-A setup and a launching pad, not exactly every pitcher’s dream scenario. Add in the organization’s financial constraints, and suddenly big-ticket free agent starters look more like fantasy than plan.
On top of that, top-of-market starting pitchers almost always get overpaid in free agency. The A’s realistically are not going to ink someone like Framber Valdez or Ranger Suárez, and even if they could, matching inflated prices for frontline arms would be a questionable use of limited resources. Overpaying for name value alone rarely works out for teams operating on tight budgets.
That doesn’t mean the A’s should sit out the pitching market completely. Instead, the smarter strategy is to identify a small group of targets who are worth stretching for — players who may not be aces but can stabilize the staff and bring intangible value as well. Think of them as “holy grail” options for this specific roster: pitchers where going a little above your usual comfort level actually makes sense.
Chris Bassitt immediately jumps to mind. He’s a familiar face after six seasons in Oakland, and his profile remains compelling. He’s projected for a reasonably sized contract — something in the neighborhood of two years at an upper-midrange total — and while he’s no longer a true number two starter, he can still function as a very dependable number three. His deep pitch mix and consistent ability to throw strikes, with walk rates below three per nine in most of his recent seasons, make him the kind of veteran who can anchor a rotation of younger arms.
Where the A’s might actually have an edge is by offering Bassitt something other teams hesitate on: an extra year of security. If his market largely tops out at two-year deals, Oakland could stand out by proposing a third. If someone goes to three, the A’s could consider pushing to four. Yes, Bassitt will be 37 at the start of the 2026 season, which raises understandable concerns about longevity. But there’s a twist that makes this less scary: he has already shown he can thrive in a bullpen role in high-leverage situations, particularly in October.
That means the back end of his contract doesn’t have to be wasted if his days as a full-time starter wind down. He could transition into a multi-inning reliever or high-leverage weapon, turning what might otherwise be a dead year into a meaningful role. It’s a creative way to squeeze extra value out of a veteran deal — and a test of whether the A’s are willing to think flexibly about role and usage instead of rigidly labeling players.
Tyler Rogers is the other “holy grail” type arm who fits what Oakland should be chasing. He’s about to turn 35, but his profile is uniquely designed to age gracefully. Rogers doesn’t rely on premium velocity; instead, he lives off deception, command, and that unusual submarine delivery that hitters never quite seem to get comfortable against.
Because his game is built more on movement and location than raw stuff, the usual sharp decline phase for hard-throwing relievers may not apply to him in the same way. His motion also comes with an added bonus: submarine deliveries are widely considered to be among the least stressful on the arm, potentially lowering injury risk over time. For a team that can’t afford to throw money at broken bullpen pieces, that matters.
Projections suggest Rogers might only command a two-year deal at around a mid-level total value. This is exactly the kind of situation where the A’s should be willing to step in aggressively. Offering three years at a slightly higher overall number, but similar annual value, could be enough to win the bidding without entering reckless territory. In fact, even nudging to a four-year deal in the low-thirty-million range could be justified if the front office believes his style will hold up.
Yes, that’s a bold stance on a reliever in his mid-30s — and some fans will argue that investing heavily in bullpen arms is risky no matter who they are. But if there were ever a type of reliever to bet on aging well, it’s the one who doesn’t depend on throwing gas and has already proven durable. Would you be comfortable committing that long to a uniquely styled reliever, or is that pushing the envelope too far?
Putting It All Together
Imagine an offseason where the A’s manage to land Jake Cronenworth, Chris Bassitt, and Tyler Rogers. The financial impact would be meaningful but not catastrophic — roughly a $30 million bump in payroll — and the cost in prospects would likely center around a mid-range name rather than the very top of the system. That’s not cheap, but it isn’t franchise-breaking either.
Now picture that group joining a roster where prospects like Gage Jump and Leo DeVries are waiting at Triple-A, ready to knock on the big-league door. Suddenly, the A’s don’t look like a team stuck in limbo; they look like a club that can go toe to toe with teams like the Seattle Mariners as soon as 2026, especially if a few young players pop sooner than expected. It’s not a fantasy superteam — it’s a realistic, targeted upgrade path.
The real question is whether the front office is willing to lean into this moment. Standing still while other teams make aggressive, calculated moves is a choice too — just rarely the right one for a franchise trying to re-establish credibility with its fans. The stove is on, the ingredients are sitting on the counter, and everyone’s hungry for something more than minor-league depth signings.
So what do you think: should the A’s push chips in for players like Cronenworth, Bassitt, and Rogers, or stay conservative and protect every prospect at all costs? And if you had to pick just one of those targets, who would you go after first — the steady infielder, the dependable starter, or the unconventional reliever? Drop your take: is this vision smart, reckless, or exactly the kind of bold plan the A’s desperately need right now?
