Cubs offseason takeaways: playoffs, free agents and Owen Caissie

The Chicago Cubs’ latest postseason run didn’t just expose the intensity of October baseball—it really spotlighted how fragile and thin their pitching depth is.

Now, as the organization looks ahead to 2026, the front office and manager Craig Counsell are staring at a pivotal winter. How aggressively will they invest in starting pitching, and how do they balance immediate needs with a still-developing farm system?

Chicago Cubs Enter 2026 Offseason With Pitching as Top Priority

The narrative around the Cubs isn’t about rebuilding anymore. A 92-win season and a nine-game jump in the standings show this club is built to contend now.

But missing the NL Central crown and ending up in the wild-card grind really exposed just how thin their margin for error is, especially on the mound.

Four elimination games in October drained the pitching staff. Counsell, who’s managed deep playoff runs before, didn’t sugarcoat it: the Cubs have to rotation-with-soroka-and-kittredge-acquisitions/”>upgrade their starting rotation if they want to survive and advance in future postseasons.

Craig Counsell’s Message: More Quality Starters, Not Just More Arms

Counsell’s takeaway from October? Quality starting pitching is the foundation of sustainable postseason success.

The Cubs weren’t short on effort; they just didn’t have enough fully trusted options. Injuries and usage patterns forced them into matchup-based scrambling when they needed stability.

That lesson is shaping the front office’s offseason priorities. Depth matters, but they’re focused on pitchers who can handle 25–30 starts and still have something left for October.

Shota Imanaga Returns, But Rotation Questions Remain

One major domino has already fallen. Shota Imanaga accepted the Cubs’ one-year, $22.025 million qualifying offer, so Chicago gets a frontline left-hander back for 2026.

It’s a big win, both financially and competitively, for a club that really couldn’t afford to lose a top starter.

Yet Imanaga’s return doesn’t close the book on the rotation. If anything, his decision gives the Cubs a higher floor, but they still have work to do.

Injuries Exposed the Rotation’s Thin Margin

The Cubs’ October strain started long before the postseason. Injuries to Justin Steele and prized young starter Cade Horton undercut the rotation’s ceiling at the worst possible time.

What should have been a strength became a precarious balancing act. Without both at full strength, Counsell had to lean heavily on whoever was available in high-leverage spots.

The result: a staff stretched to its limits, and a clear message heading into winter—Chicago needs more proven starting pitching to withstand a 162-game season plus October.

Cubs Navigate a Complex Pitching Market

The Cubs didn’t just sit back and watch the pitching market unfold. They jumped right in, including a pursuit of a familiar name with big upside.

Missed on Dylan Cease, But Not at Any Cost

Chicago was involved in negotiations for Dylan Cease, a former Cubs farmhand who ultimately landed a massive deal with the Toronto Blue Jays.

The front office liked the pitcher, but they didn’t like the price enough to match what Toronto offered.

General manager Carter Hawkins said the current free-agent landscape hasn’t produced full-blown sticker shock. It’s about context—what a player costs versus how he fits the roster, the payroll, and the long-term plan.

In Cease’s case, the calculus just didn’t justify the commitment Toronto was willing to make.

Thin Pitching Prospect Pool Puts Pressure on Development

The Cubs’ pitching prospect depth is thin. They can’t just assume the next wave of arms will naturally show up at Wrigley in a year or two.

That makes both free agency and player development crucial.

Jaxon Wiggins: High-Octane Arm With Big Upside

One name drawing internal optimism is Jaxon Wiggins. The right-hander is still more projection than finished product, but his tools jump off the page.

He’s recovering from Tommy John surgery, yet he’s already flashed a fastball in the upper 90s and even hit 100 mph, paired with a sharp breaking ball.

If he can refine his command and stay healthy, Wiggins could follow a path similar to Cade Horton, moving quickly once everything clicks.

Still, banking on rehab arms is risky. The Cubs can’t rely solely on internal growth to fix their rotation problems.

Owen Caissie and the Position Player Pipeline

While pitching dominates the headlines, the Cubs also have a notable young talent on the position-player side prepping for a bigger stage in 2026 and beyond.

Caissie Eyes Wrigley and the World Baseball Classic

Outfielder Owen Caissie is on track to take on a much larger role. He’s expected to compete for Team Canada in the 2026 World Baseball Classic and is training like someone ready for the Wrigley Field spotlight on Opening Day.

Internally, there’s belief he can step in and eventually take over the type of everyday impact role you’d expect from a star corner outfielder—he’s even being groomed to replace the production of a player like Kyle Tucker.

If Caissie emerges, he could give the Cubs both lineup thump and financial flexibility as they invest heavily in pitching. It’s a lot to ask, but the upside is hard to ignore.

What It All Means for the Cubs’ 2026 Blueprint

The Cubs aren’t just aiming for October anymore. They want to stick around and actually make some noise when they get there.

After a 92-win season and a tough postseason, Chicago’s front office faces a clear task. Build a rotation that can carry this core deep into October—not just once, but again and again.

 
Here is the source article for this story: Cubs takeaways from playoffs and free-agent deals, Owen Caissie’s WBC decision and more