The Chicago Cubs feel that they’ve put together a good, complete team that can make a deep playoff run this season. And they did it with a little of everything– some key free agent acquisitions, a big trade, and the rise of various internal pieces.
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Looking beyond the 2026 season, though, there are some real concerns.
As much as half the team could be gone via free agency at the end of this baseball year. Chief among the potential outgoing talents are core team components Ian Happ, Nico Hoerner, Seiya Suzuki, Matthew Boyd, Jameson Taillon, and Shota Imanaga.
Pressure’s on Ian Happ ahead of free agency

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Happ, especially, has to feel some pressure. He’s been a Cub since the start of his pro career as a 2015 no. 1 draft pick. Heading into his tenth season in the majors, he’s staring down the possibility that Chicago may decide that they can only keep one of their corner outfielders and that the team will have to choose between him and Suzuki.
The 31-year-old is saying all the right things as Opening Day approaches, although it’s still pretty clear that the pending free agency is weighing on his mind. He’s doing his best to focus on this season and on winning with his fellow Cubs.
“The focus is just so much on this group,” Happ told The Athletic. “Both enjoying it and playing really good baseball together. It makes it a lot easier when you’re on a good team that’s going to compete that that can be the main focus.”
When asked if he’d talk to the Cubs regarding an extension during the season, he’s not sure, but he’s also understanding why the front office may not want to engage in contract talk as games are being played.
“It’s hard because they’re focused on this year and winning as well,” he asserted. “If their mind isn’t in that place — I want their focus to be on winning this year, and my focus to be on winning this year. So let’s do that.”
“That’s their job, right?” Happ added. “To figure out what are the things that are valued and how does that equate. My job is to be the best player I can be. You can’t think about what the model is going to spit out on you. You have to play and impact winning, impact the organization.”
A big decision awaits

Cubs president of baseball operations Jed Hoyer will find himself in a tough spot at the end of this season and he was well aware of that as last year closed.
“I think my hope and expectation is that we’ll have extension talks with a number of our players this offseason,” Hoyer said at his end-of-season press conference last year. “I think that we have a number of players that we’d love to keep long term, and we’ll have those conversations. We have clean books going forward, we have good players, and we’ll have those conversations.”
Hoyer’s decision, when it comes to outfield, seems to be Happ or Suzuki. While Happ has been the much more consistent player and a Gold Glove-level fielder, Suzuki has the greater offensive upside and is coming off a career year with the bat.
Big decisions are ahead for all involved. For now, Happ and the Cubs just seem focused on winning.
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