According to sources, the Pirates plan to be spenders on the free-agent market, something they haven’t done over the past decade.
The left side of the infield and the corner outfield spots seem like the most obvious places for the Pirates to target, though the club hasn’t signed a free-agent hitter to a multi-year deal since December 2015, when they gave John Jaso a two-year, $8 million contract.
“We have tried,” Cherington said. “It’s bound to happen; the odds increase a little bit each offseason with the combination of players seeing the strength of our pitching and the opportunity to win with that pitching foundation, and a little bit more flexibility. I think the combination of those two things give it a better chance, but we’ll find out. The bottom line is we want to add to our position player group and we’ll explore all kinds of ways to do that.”
It’s unclear exactly how much the Pirates plan to spend, but sources estimate it at roughly $30-40 million in payroll for 2026. The departures of Ke’Bryan Hayes, David Bednar and Isiah Kiner-Falefa cleared significant space on the payroll last season, while free agents Andrew Heaney, Andrew McCutchen and Tommy Pham accounted for about $14 million in 2025.
The Pirates went 71-91 in 2025, their seventh straight losing season, extending their streak to 10 seasons since they last made the playoffs.
“We need to win more games, and believe we’ll have flexibility to pursue some things in free agency and trades,” Cherington said. “We need to add to the offense and we’ll be disappointed if we don’t; what that looks like, we don’t know. We’ll pursue lots of stuff, I’m sure.”
The Rays will be active on the trade market this winter, and to a lesser extent, in free agency. But Tampa Bay will be adding an important piece to their club regardless of what the roster looks like when Opening Day arrives: their home.
“We couldn’t be more appreciative of the Yankees offering up Steinbrenner, the accommodations, in a really difficult situation,” Rays president of baseball operations Erik Neander said. “Their generosity, their setup, was the absolute best you could have hoped for or asked for under the circumstances. That being said, it’s still very much like sleeping on your friend’s couch rather than living in your own home.”
The Rays went 41-40 at Steinbrenner Field last year, going 77-85 overall for their second straight losing season after six consecutive winning records. By the time the season reached August, the toll it was taking on their players was apparent to Neander.
“There was never a complaint; everyone understood that we were there because of something much more important than baseball, and they went about their work all year like true professionals,” Neander said. “Having said that, when you’re not home for that long, it does get a little exhausting. It kicked our [butt] a little bit more than we thought.”
The Rays averaged 49.5 wins per year at the Trop between 2021-24, so while the ballpark may not have some of the amenities that the newer stadiums around the league do, Neander believes his team will benefit greatly by returning to its familiar surroundings. Fly-ball pitchers like Ryan Pepiot and athletic position players like Chandler Simpson and Jake Mangum should benefit from the more spacious dimensions and controlled environment.
“We learned how much that matters by being away from it,” Neander said. “We’re just looking back to getting into that natural habitat that we’ve enjoyed for so long. I’ve heard the words, ‘I missed the Trop’ far more often in the last six months than I probably would have ever expected. That’s our home. It will be helpful to be back there and get back into a normal routine.”
The Royals made a huge commitment – and statement – in February 2024 when they gave Bobby Witt Jr. an 11-year, $288.8 million extension following his first two years in the league. The deal could be worth as much as $377 million over 14 years thanks to a club option at the end of the 2034 season.
On the other hand, it could also be torn up after the 2030 season, as Witt has opt-out clauses at the end of each season between 2031-34, allowing him to go back on the open market.
Do Witt’s opt-outs create a sense of urgency for the Royals to contend?
“I don’t know if I would use the word urgency, but there’s an awareness that we feel like we are in a window right now,” said Royals GM J.J. Picollo. “Our goal is to extend that window beyond 2030, but we’re in a window where we have one of the best players in the game. Our pitching staff going into 2026-27, we feel like we have enough, at least on paper. We have to build around him to help us achieve what we want to achieve, but we’re in that window where the expectations are a little bit higher.”
The Royals reached the postseason in 2024, sweeping the Orioles in the Wild Card round before falling to the Yankees in four games in the ALDS. Kansas City went 82-80 last season, finishing five games out of the final AL Wild Card spot.
“It was a kick in the teeth,” Picollo said. “We didn’t assume we were going to be in the playoffs, but it felt like at times we played like we thought we were a playoff team – then we found out we weren’t. Hopefully we grow and learn from it. Was the year a total disaster? No. I still think we did some nice things.”
The Royals are focused on the outfield market, looking to add a left fielder – ideally one who can play every day – and a right-handed bat who can complement the left-handed hitting Jac Caglianone in right field.
“We don’t want to spend a lot of money on the short side of a platoon, but the reality is we need it,” Picollo said. “If we can find the right person, the right bat to complement Cags, that would be great.”
Kansas City’s payroll should be in the $140 million range, which is where it was last season, though Picollo said owner John Sherman has shown a willingness to consider anything if it’s the right move for the club.
“If you look at going into 2023, we were at $100 million, then we jumped to 130, then we jumped to 140; that’s a 40 percent increase in a two-year period,” Picollo said. “He’s made a pretty significant commitment, and now it’s on us to make this work. He’s always been open-minded; we did it last year with [Carlos] Estévez at the end of the winter. That 140, it’s not a hard 140, but we have to be able to go to him and say, ‘This makes a lot of sense.’”
