The MLB offseason is in full swing, with the likes of Kyle Schwarber, Pete Alonso and Edwin Diaz signing at an otherwise-quiet Winter Meetings. Most front offices around baseball have yet to act on promises made to their fanbase, and star players on the roster.
Whether those stars play for a contender (such as Aaron Judge and Bryce Harper) or pretender (Paul Skenes and Corey Seager) doesn't make much of a difference. Players expect progress year over year, and they aren't always granted that wish.
Jose Ramirez, Cleveland Guardians
Jose Ramirez made a statement once the Guardians were knocked out of the AL Wild Card series by the division rival Tigers: He's tired of doing it all on his own. In an interview after the season ended, Ramirez made it clear the Guardians front office hasn't held up their end of the bargain.
"Things are going to change for the 2028 extension talks.," Ramirez said. "The General Manager didn’t do what we talked about back then. They were supposed to take advantage of my discount and build a team to win."
Ramirez has arguably left nine figures on the table to stay in Cleveland. Even during that interview, he told Guardians fans how much he enjoys playing for the organization and living in the city during the season. All he wants is for that love to be reciprocated.
The 33-year-old Ramirez won't reach free agency until after the 2026 season. By then, who knows what kind of player he'll be, as Ramirez will be in his late-30's. His game should age well, as he's not particularly reliant on any one facet. Hopefully the Guardians put a real winning roster around Ramirez while they still can.
Bobby Witt Jr., Kansas City Royals
Bobby Witt Jr. is one of the game's most electric stars. The Royals have some pieces, but are still a ways away from competing for the AL Central crown. Both the Tigers and Guardians are a step ahead, and even should Detroit lose Tarik Skubal this winter via trade, it's tough to argue AJ Hinch's team wouldn't be well-positioned to jump the middle tier of the Central despite that rotation weakness.
So far this offseason, the Royals have signed Lane Thomas and Alex Lange. The Royals front office, which has promised fans for far too long that they plan to spend, hasn't been in on many of the top-tier free agents available.
After the 2025 season, Royals owner John Sherman took a soft stance on the team's 2026 spending, and it rubbed some fans the wrong way.
“I think you have to have the right mix of players,” Sherman said. “On the pitching staff, we’ve got (Seth) Lugo and (Michael) Wacha, they’re veteran guys, but we’ve got young guys making the minimum," Sherman said. "That mix of salary, you’ve got to have both for a team like ours. I’m comfortable there. But to me, it’s always been with J.J.: What makes us better? If there’s something that makes us better, let’s talk about it.”
The Royals principal owner doesn't sound eager to add payroll. Witt Jr. isn't going anywhere, but you can bet he'll make his feelings known if this disappointing offseason continues.
Paul Skenes, Pittsburgh Pirates
Paul Skenes won his first NL Cy Young award for his excellent 2025 season. While he was drafted just a few short years ago with the No. 1 overall pick, Skenes has already been mentioned in trade talks. Per one former Pirates teammate, Skenes once mentioned how much he'd love to play for the Yankees when voicing his frustrations with Pittsburgh's front office and lack of urgency.
While Skenes refuted that report, it's easy to see why it made the rounds. Skenes would be just the latest in a long run of talented Pirates players to be wasted by ownership, and eventually traded away for more prospect capital. If there were an award for top farm system, the Pirates would surely hang a banner.
This winter was supposed to be different, and still very well might be. The Pirates were linked to both Kyle Schwarber and Pete Alonso. Heck, they reportedly made a nine-figure offer for Schwarber before he re-signed with the Phillies. Ben Cherington and Bob Nutting are trying, but their reputation is getting the best of them.
Why would any high-priced free agent want to sign in Pittsburgh, knowing full well that once they sign on the dotted line, Nutting will go back to pinching pennies? That's not how a contender is built, and just another reason why Skenes and the Pirates have a reputation problem on their hands.
Tarik Skubal, Detroit Tigers
There's no better way to get on a two-time AL Cy Young winner's bad side than to try to trade him one year ahead of free agency. The Tigers don't believe they can afford a Tarik Skubal extension, and for the most part, they are correct. Skubal will want at least $400 million should he finish top-5 in Cy Young voting once again in 2026. Skubal is also a Scott Boras client, so the likelihood he tests free agency is high.
Skubal's inclusion on this list isn't because he has some personal vendetta against Detroit. He loves the city and pitching for the Tigers. It's because there's been little-to-no movement on a possible extension to keep him with the team long term. Rather, Scott Harris all but confirmed Skubal's been discussed in trade talks at the Winter Meetings.
The Tigers want to win now. One would assume their best way to win a World Series would be to keep Skubal on the roster. That's a conundrum for Harris, though, as they risk losing their ace for nothing after the 2026 season if they sit on their hands. Harris is likely to make the unpopular decision to trade Skubal. Whether Tigers fans riot or not will likely depend on the return, and what Detroit does with the money they could've just handed the best starting pitcher on the planet.
Corey Seager, Texas Rangers
The Texas Rangers are cutting payroll. The days of competing for a World Series in Arlington are gone, at least with this core. Texas already traded Marcus Semien to the New York Mets. They let Adolis Garcia walk, and he signed with the Phillies on Monday. Seager could be next, and would likely bring back the best return for the Rangers via trade.
Seager is just 31 years old, and while he does have some injury issues, he's had three straight seasons of at least 5.0 bWAR. Last season, he had an .860 OPS and is by no means trending downward as he enters the later stages of his prime. The question, then, is why the Rangers seem so eager to trade him?
Chris Young told reporters at The Winter Meetings that he expects the Rangers Opening Day payroll to be under $200 million. The Rangers ended last season with a payroll of $226 million. Young doesn't seem to think it'll make much of a difference.
“I just don’t feel sorry for ourselves that our payroll is going to be smaller than it was,” Young said. “I don’t think it’s going to inhibit us. …I’m a competitor. It doesn’t deter me. It means we better be better at our jobs. And that’s what I expect to do. I think the biggest thing that we need to do is play up to our expectations. This past season and the year before, we did not do that.”
Dumping Seager would help the Rangers reach that mark, but it would also eliminate their hopes of winning the AL West in 2026.
Aaron Judge, New York Yankees
Aaron Judge's Yankees took a step back in 2025, as New York not only didn't reach the World Series for the second-straight season, but also failed to win the AL East. Now looking up at the Toronto Blue Jays, and level with the Boston Red Sox, it'd be fair to expect a big offseason in the Bronx. Not so fast!
Hal Steinbrenner and Brian Cashman aren't chomping at the bit to add to the team's payroll for 2026. Steinbrenner has said as much, despite whiffing on Juan Soto's $765 million last winter.
"Would it be ideal if I went down [with the payroll]? Of course," Steinbrenner said on a video call with reporters. "But does that mean that's going to happen? Of course not. We want to field a team we know could win a championship -- or we believe could win a championship."
Steinbrenner pushed back when reporters mentioned that the Yankees made a profit in 2025, perhaps previewing what's to come for Judge this offseason.
"I don't want to get into it, but that's not a fair statement or an accurate statement," Steinbrenner said. "Everybody wants to talk about revenues. They need to talk about our expenses...Nobody spends more money, I don't believe, on player development, scouting, performance science. These all start to add up. If you want to go look at the revenues, you got to somehow try to figure out the expense side as well. You might be surprised."
Judge committed long term to the Yankees. He is their captain, after all. But, one season after losing a player of Soto's caliber to a crosstown rival, one would hope the Yankees would show a little more urgency to reach baseball's mountaintop once again. Instead, they're content with good enough.
Juan Soto, New York Mets
It has been a brutal offseason for the New York Mets. Just weeks after Juan Soto told New York media he'd prefer to run it back with many of the same Mets stars who have since signed in new cities, David Stearns is left sitting on his hands.
Sure, the Mets signed Jorge Polanco. That is, indeed, something. Stearns did what Stearns always does, and chose not to overpay for a closer in Edwin Diaz. Because of that long-held belief, Diaz signed with the Los Angeles Dodgers. That move could haunt Mets fans this season as the Dodgers chase a three-peat. To make matters worse, it turns out the Mets offered Diaz just as many years, and nearly matched with deferred dollars. Diaz didn't care. He just wants to win.
Losing out on Alonso to the Baltimore Orioles is a far more painful reality the Mets must embrace. Alonso is the franchise's all-time leading home run leader. He's still in his early-30's and is coming off one of the better seasons in his career. He should thrive at Camden Yards, and the Orioles are arguably in a better position to win in the AL than the Mets are in the National League thanks to the Dodgers.
Soto took $765 million from Steve Cohen prior to last season with the expectation the Mets would keep building around him. In his first offseason with the team, Soto is finding out the hard way that billionaires don't always keep their promises.
Bryce Harper, Philadelphia Phillies
Why should Bryce Harper be upset? The Phillies kept Kyle Schwarber around on a five-year deal and signed Adolis Garcia on Monday. The Phils have some promise, but their product has grown stale. Philadelphia has lost its last two postseason series, first in 2024 to the New York Mets, and last season to the eventual World Series champion Dodgers. There's a very real chance that the Phils best opportunity to win their own title has passed them by.
So, what did the Phillies do? Well, they kept manager Rob Thomson and even gave him an extension, and they've failed to make any early moves to shake up the clubhouse. That includes keeping Schwarber, though he is universally beloved in Philly.
To make matters worse for Harper, president of baseball operations Dave Dombrowski challenged him in his end-of-season press conference, and to hear Dombrowski tell it, the comment took on a life of its own.
“Of course, he’s (Harper) still a quality player,” Dombrowski said. “He’s still an All-Star caliber player. He didn’t have an elite season like he has had in the past. And I guess we only find out if he becomes elite or if he continues to be good...Really, he’s the one who will dictate that more than anything else. That’s what it comes down to. So I don’t think he’s content with the year that he had. And, again, it wasn’t a bad year. But when I think of Bryce Harper, you’re thinking elite, right?"
"I've been reading that the Phillies may trade Bryce Harper. That couldn't be further from the truth."
— Foul Territory (@FoulTerritoryTV) October 23, 2025
Dave Dombrowski says Bryce Harper is an elite talent, and his comments weren't meant to be criticism. pic.twitter.com/HMJY6TjPsv
Harper took this the wrong way, suggesting he gave his all to Philly, and he was injured for much of the season.
“I have given my all to Philly from the start,” Harper told The Athletic. “Now there is trade talk? I made every effort to avoid this. It’s all I heard in D.C. (with the Nationals). I hated it. It makes me feel uncomfortable.”
Harper is unlikely to be traded in part do to his contract, but Dombrowski got on one of his best players' bad side real quick. Factor in that with a complacent offseason, and Harper has a lot to be upset about before spring training.