Cubs’ Winter Plan: What Fans Need to Know About Offseason

The Chicago Cubs are heading into the 2026 season with a pretty clear goal: fix the pitching. At the recent Las Vegas GM meetings, President of Baseball Operations Jed Hoyer and GM Carter Hawkins talked about a plan to address the pitching problems that popped up late in 2025.

They seem confident in their group of position players — even though free agent Kyle Tucker is probably leaving. The front office believes getting back to contention really depends on bringing in top-tier starters and bullpen arms that can handle big moments.

Strategic Pitching Focus for 2026

The Cubs’ offense sputtered in the second half of 2025 and during the playoffs. That made it obvious they needed steadier run prevention.

Hoyer hinted that, while they’ll look at batting depth, pitching is the real priority. They want a frontline starter to go with Matthew Boyd, Cade Horton, Justin Steele, and Jameson Taillon — that’s at the top of the shopping list.

Key Rotation and Bullpen Targets

They’re also looking to beef up the bullpen, especially after those close-game meltdowns last season. The plan is to mix proven vets with up-and-coming arms, hoping to build a pitching staff that can actually get them deep into October.

The Shota Imanaga Decision

One big call this offseason is what to do about starter Shota Imanaga’s contract. The Cubs didn’t pick up his three-year, $57.75 million option, but they did extend a qualifying offer for $22.025 million.

Most expect Imanaga to decline it, which means he’ll probably look for a new multi-year deal somewhere else. If that happens, the Cubs need to find a replacement starter on the market.

Payroll Flexibility and Resource Planning

Money’s not really an issue here. The 2025 payroll sits around $214 million, and outside of Dansby Swanson’s $28 million salary in 2026, there aren’t many big long-term contracts.

That gives Hoyer and Hawkins some room to get aggressive with free agents or trades. They can fill a few roster holes without putting the future at risk.

Learning from Past Moves

Hoyer still seems a bit frustrated about missing out on Alex Bregman, which kind of sums up their careful approach to big-name signings. Last year’s midseason trades didn’t do much, so management is tweaking their strategy — they want new additions to make an immediate impact, not just fill a spot.

Offensive Uncertainty Post-Kyle Tucker

Replacing Kyle Tucker’s bat is a real question mark as winter meetings approach. Since it’s almost certain he’ll leave in free agency, the front office might just look at internal options like Owen Caissie.

They could bet on younger guys stepping up, which would save money for pitching and give prospects a shot at real playing time.

Possible Offensive Scenarios

If they do go outside the organization, expect them to look for hitters who bring both power and on-base skills. Still, with Hoyer backing the current position group, it feels more likely they’ll promote from within instead of making a splashy signing.

Fan Expectations and Organizational Outlook

Wrigley Field keeps bringing in strong revenue, so ownership can back the front office’s plans. Cubs fans, who know all about the ups and downs, will be watching to see if this pitching-first approach pays off.

With the Cubs saying they’re “ready to play a game tomorrow,” the message is pretty direct: the core is solid, but they know they need a few key upgrades.

The Road Ahead

The winter meetings are coming up fast. The Cubs’ offseason choices will show if their focus on pitching can actually cover up those nagging offensive issues.

They’ve got some financial flexibility, a set of clear goals, and a front office that seems fired up. That could mean some big moves are on the way—at least, if they play their cards right.

Key Offseason Priorities:

• Land a frontline starting pitcher to anchor the rotation.
• Add a couple of high-leverage bullpen arms.
• Figure out how to replace Kyle Tucker’s offensive production.
• Use payroll flexibility to really improve the roster.
• Take advantage of strong revenue streams and future event hosting chances.

 
Here is the source article for this story: Column: Winter is coming, but the Chicago Cubs’ offseason strategy is on a need-to-know basis