Cubs Face Pivotal Offseason: Will Jed Hoyer Finally Pull the Trigger on a Big Trade?

With most of their long-term payroll flexibility lining up with the end of the current Collective Bargaining Agreement in 2026, the Chicago Cubs are sitting on a rare kind of leverage this offseason. They’ve got financial room to maneuver, a fan base hungry for postseason relevance, and a roster that-while promising in places-still needs serious reinforcement, especially in the starting rotation.

But here’s the thing: if the past few offseasons are any indication, Cubs fans shouldn’t expect a spending spree. Outside of last winter’s Kyle Tucker blockbuster (a rare swing from the front office), Tom Ricketts and Jed Hoyer have largely played it safe. They’ve stayed out of the deep end of the free agent pool, even as the team continues to rank among the most profitable in the league.

So if big checks aren’t being written, the trade market becomes the logical path forward-and this winter’s crop of potential trade targets is tailor-made for a team like the Cubs. According to MLB Trade Rumors’ top 40 list of likely trade candidates, the Cubs could realistically be in play for as many as eight of the top 10 names.

Now, let’s be clear: not every name on that list is a fit. Freddy Peralta and Sonny Gray, both key arms for NL Central rivals, are highly unlikely to be shipped to a division opponent.

Peralta, in particular, was a workhorse for the Brewers in 2025 and is expected to get some Cy Young consideration. Milwaukee’s not about to hand him over to a team they face 13 times a year.

But beyond that? It’s wide open.

The list is loaded with pitching-eight of the top 10 names are arms-and several of them have already been linked to the Cubs in past trade deadline chatter. Think Mackenzie Gore, Joe Ryan, Pablo López, Sandy Alcantara.

These aren’t fringe guys. These are legitimate rotation upgrades, frontline starters who could immediately elevate a Cubs staff that, while solid in stretches last season, lacked the kind of dominance needed to make a deep October run.

Before Hoyer starts dialing up rival GMs, though, he’s got to figure out what to do with Shota Imanaga. The lefty was electric for most of his rookie campaign in 2024, but the wheels came off late, and his home run issues made him a liability in high-stakes postseason moments. His contract situation is complicated and could go in a few different directions this winter, depending on how the Cubs choose to handle his option.

Beyond Imanaga, the Cubs do have some returning arms to work with. Matthew Boyd, who earned his first All-Star nod in 2025, is back.

So is rookie Cade Horton, a promising right-hander who showed flashes of real potential but is still finding his footing in the big leagues. Jameson Taillon enters the final year of his four-year, $68 million deal, and Justin Steele-who missed nearly all of 2025-should be back in the mix at some point, which would be a major lift for the rotation.

Still, outside of Horton (and even that’s a bit of a wait-and-see), this is a group that could use a serious injection of talent. The Cubs need a horse-someone who can take the ball every fifth day and give them a real shot to win, especially in the back half of the season when the pressure ramps up.

The good news? The market is there.

The Cubs have a top-heavy farm system with enough high-upside talent to get a deal done. The question, as always, is whether Hoyer and the front office are ready to push their chips in and make the kind of aggressive move that signals they’re serious about contending-not just in theory, but in practice.

This offseason may be the turning point. The pieces are in place.

The targets are available. Now it’s up to the Cubs to decide whether they’re ready to act like a team that wants to win now-or continue to play the long game while the rest of the division gets better around them.