Buster Olney
Major League Baseball’s winter meetings begin next week, and, although we have seen some action already, relatively little has been resolved so far this offseason.
More than 100 relievers are unsigned, major stars from Japan remain up for grabs and many of the best free agent hitters — Kyle Schwarber, Kyle Tucker, Bo Bichette — are still available. Some executives also expect a flurry of trades to be made, as potential dealers account for the possibility of labor strife in 2027 and make moves sooner rather than later, perhaps with the likes of MacKenzie Gore, Joe Ryan and Sandy Alcantara.
“What I’m hearing when I talk to teams is pitching, pitching, pitching,” one agent said. “Everybody is looking for pitching.”
With all that in mind, here are the most glaring needs for some of baseball’s contending teams.
Philly’s everyday lineup has winter potholes.
There has been a broad assumption around the industry that Schwarber will return to the Phillies because, well, they can’t afford to let him go. To not sign him would be unthinkable, given what he provided in stability (he played in 162 games), power (56 homers and 264 times on base via hit, walk or HBP) and clubhouse presence.
But he’s not under contract yet, and neither is catcher J.T. Realmuto, the leader of the pitching staff. The Phillies also need outfield upgrades and to find a taker for Nick Castellanos.
Their pitching is actually in decent shape, thanks to Cristopher Sanchez & Co., in a winter in which everybody is talking about pitching. But for a team that’s theoretically in its window to win, the Phillies have a lot of work to do within their position player group — and it’s going to cost them.
New York’s signing of closer Devin Williams and trade for Marcus Semien are just the first two of what rival execs and agents expect to be many major moves devoted to run prevention. But all eyes in Mets nation — most notably, those of the owner who has now spent billions trying to win the franchise’s first championship since 1986 — will be on the search for someone to front the rotation.
On one hand, the Mets’ decision to triage their late-season collapse with the rookie pitching trio of Nolan McLean, Jonah Tong and Brandon Sproat was understandable — in that moment, they were the best available options. On the other hand, that one of the highest-spending teams tried this underscored just how thin the Mets were — and still are — in the front of their rotation. This cannot happen again.
It’s very possible that McLean will build on his remarkable late-season performance, and it would be reasonable for the Mets to anticipate a bounce-back year from Sean Manaea. Maybe Tong and/or Sproat will also emerge. And maybe David Peterson will pitch well all the way through the 2026 season, avoiding another late-season slide.
But the Mets need The Guy, and there are candidates in both the trade and free agent markets. Tarik Skubal could be a possibility, although officials with other teams seriously doubt that Mets head of baseball operations David Stearns would give up the vault of prospects needed to acquire Skubal for 2026 and then pay the $400 million-ish cost of his free agency next fall. The Mets could angle for a Joe Ryan trade, although some execs report that Minnesota hasn’t signaled a willingness to deal him. They could target Framber Valdez, maybe the best of the free agent starters.
Whoever it is, they need an ace — badly.
This has been their need for, well, the better part of a decade. Here is how Royals outfielders have ranked in fWAR in the majors over the past five seasons:
2021: 1.6 fWAR, 29th
2022: 4.4, 19th
2023: 3.3, 23rd
2024: 1.2, 27th
2025: -1.1, 30th
The Royals have 9.4 fWAR from all of their outfielders over the past five seasons combined. Aaron Judge had 10.1 fWAR in 2025 alone.
Jac Caglianone could help to improve these numbers in 2026, but the Royals are likely to also look elsewhere, as they did last winter, when they swapped starting pitching (Brady Singer) for a hitter (Jonathan India). Once again, they can work from their rotation depth to acquire an outfielder at a time when contenders are talking about … pitching, pitching, pitching.
Maybe the Braves already acquired the player who will take the bulk of the playing time at shortstop with the trade for Mauricio Dubon. Maybe they will try to cover the position with a combination of players, rather than chase a star shortstop. But Atlanta needs significantly more from the position than it got in 2025 — 0.5 WAR, which was tied for 28th in MLB. The bar for potential improvement is low, but if the Braves are going to bounce back from the frustrating 76-win season of 2025, they need better — much better — production in this spot.
Bichette might be the best available free agent who has played shortstop, but given the regression in his defensive performance at the position, it’s hard to find evaluators who believe he has a future at shortstop. And history has shown that Braves head of baseball operations Alex Anthopoulos does not pay sticker price when signing free agents. He didn’t for his own shortstop, Dansby Swanson, or for other former Braves Max Fried and Freddie Freeman. An Atlanta match with Bichette, whose market value stems from his offensive abilities, seems highly unlikely.
Since the Red Sox allowed Schwarber to walk as a free agent following the 2021 season, there has been major regret within the organization over that decision — not only because of the production that Schwarber provided, but also because of his leadership. Boston faces a similar quandary now with Alex Bregman: After an excellent experience with him in their clubhouse in 2025, the Red Sox know firsthand how he helps other players, especially younger ones.
But retaining Bregman will be expensive, and it’s not clear how much the Red Sox will spend coming off what was a year of progress. If they pay to retain Bregman, they will still need a thumper. At the end of a year in which the division rival Toronto Blue Jays have officially emerged as one of baseball’s money monsters — joining the Los Angeles Dodgers, New York Yankees, Mets and Phillies — will the Red Sox continue to ante up for the rising cost of talent? It’s unclear.
The most notable missed opportunity for any team in the past 15 months was Baltimore squandering its chance to land Garrett Crochet — the Orioles matched up better with the Chicago White Sox than any other team, given their group of position prospects, and the $170 million deal that Crochet signed with Boston wouldn’t have been prohibitive for Baltimore. Crochet went on to lead the Red Sox into the playoffs, and the Orioles finished last in the American League East. Oh, what could have been.
Baltimore is trying to regain its footing now. The Orioles finally invested a multiyear deal in an arm by signing closer Ryan Helsley to a two-year contract over the weekend. But more is required if they’re going to take advantage of this window when Gunnar Henderson is wearing an O’s uniform.
The Orioles have Trevor Rogers, Kyle Bradish, Dean Kremer, Tyler Wells and Cade Povich among their starting pitchers for next season, but they know firsthand how pitching injuries can derail a season, and they need more rotation options. Nobody expects them to spend like the Yankees, Blue Jays or Red Sox, but Helsley is the only pitcher under contract for 2027. There has to be a greater devotion of resources this winter to this need.
New York Yankees: A veteran outfielder
One rival evaluator said it’s possible that the Yankees could go with what they currently have, now that they’ve retained Trent Grisham to play center alongside Judge in right field. That would mean a full commitment to 22-year-old Jasson Dominguez, who has yet to declare himself an everyday big league player; he had a 101 OPS+ last season and accumulated 0.5 WAR in 381 at-bats. The Yankees could bank on prospect Spencer Jones ascending into their outfield mix in 2026, after he hit 35 homers in Double-A and Triple-A this year (with 179 strikeouts in 506 plate appearances).
But moving in the direction of very young players will be hard to do, given how important veteran Cody Bellinger was to the team in 2025. He was a perfect fit in so many ways — the defense, the positional pliability, the speed, the comfort in the New York market. But some agents and rival evaluators aren’t sure if the Yankees will be willing to pay the price to either retain Bellinger or pursue fellow free agent outfielder Kyle Tucker. If not, they’ll still need to add someone with major league experience — ideally a right-handed hitter who can play center field.
Gleyber Torres was on base a lot for Detroit this past season, accumulating a .358 on-base percentage, and he’ll be back for 2026 after accepting the qualifying offer. The Tigers also have some high-end prospects who will soon manifest in the big leagues, such as shortstop Kevin McGonigle and outfielder Max Clark.
But if they keep Skubal for 2026 — which most rival evaluators believe they will do — in an effort to contend next season before he walks away as a free agent the following winter, they desperately need another masher, somebody who can produce in the No. 3, 4 or 5 spot in Detroit’s lineup and complement Riley Greene and Kerry Carpenter.
Bregman would be a nice fit — just as he would have been last winter, when the Tigers came close to signing him. A hitter like Bichette would also be ideal, but signing him would be expensive — more than the Tigers might be willing to pay to bring in someone who would project as a second baseman or third baseman in the future — and Detroit would have to use some of its payroll flexibility. The only players the Tigers have under contract for 2027 and beyond are Colt Keith and Javier Baez (whose deal expires after the 2027 season).
The Kyle Tucker of April, May and early June transformed this lineup, with his ability to get on base, hit for power and create opportunity. But it’s unclear where the bidding for Tucker‘s services will go this winter and whether it’s certain that the Cubs will consider keeping him if he’s out of their price range.
If the Cubs continue to be conservative with their budgets — and, to date, there’s no reason to think they’ll be big spenders — they’re going to have to offset the loss of Tucker in whatever ways they can. Maybe that’s by loading up on pitching by pursuing the likes of Ryan and trying to make do with an offense that ranked 20th in runs scored in the second half of 2025. Or maybe they pursue a thumper. But they need something.
As he was last winter, Bregman would be a perfect fit in how he plays both defensively and offensively. But signing him was too expensive for the Cubs last winter.
Los Angeles Dodgers: Bullpen help
Let’s be clear: This is hardly a panic situation that requires overpaying. The late-inning hole in the relief corps existed throughout October, and the Dodgers still won their second consecutive World Series title. They also have internal candidates for the closer role — including Tanner Scott, who was signed to a four-year, $72 million deal last winter — and a possible fallback option for 2026 in Roki Sasaki, who demonstrated in the playoffs that he has the ability to be a lockdown force in the late innings.
But the Dodgers still view Sasaki as a future starter — to go with their other cast of rotation stars — and given their desire for a three-peat, it would behoove them to add a reliever who could reliably take the eighth or ninth innings of big games.
Here’s one more great thing about the heights the Dodgers now occupy in the MLB universe: Veteran free agents want to play for them for a chance at a ring, to the point that they might even pass up better offers from other teams. Great players want to play for the Dodgers. At some point, they will bolster their bullpen.
