The Chicago Cubs find themselves at a pivotal crossroads this offseason – not in crisis mode, but certainly in the haze of transition. With close to $100 million available to spend (assuming they stick to the first tier of the luxury tax threshold), you’d expect the front office to be aggressive.

But the specter of a looming work stoppage after 2026 could keep their checkbooks holstered when it comes to long-term commitments. So the Cubs may look more like a team in holding mode than one swinging for the fences this winter.

That affects the big-ticket decisions – and none looms larger than what happens with Kyle Tucker. Unless Tucker decides he’s open to a short-term, prove-it deal to rebuild his value following a rough second half of the season, his return to Wrigley feels far-fetched. Most signs point to an exit.

Instead, the Cubs seem poised to roll into 2026 with the bulk of their current core – and while continuity can be a strength, in this case, it might be more of a burden. Here’s a look at several key players slated to return in 2026, and why their continued presence poses as many questions as answers for a front office trying to retool on the fly.

Ian Happ, LF: Still Here, Still a Trade Candidate

Ian Happ is the obvious name that sparks a “what if?” conversation.

Statistically, his 2025 season wasn’t a wash – a 116 wRC+ and 23 home runs is right in line with his career norms – but the journey to those numbers was anything but steady. His slumps were deeper and longer than we’ve seen in years, and his offensive inconsistency was hard to miss.

In a more flexible world, Happ would be a prime trade piece. He’s a switch-hitting, defensively capable outfielder with proven pop who could headline a deal for a front-line starter – exactly what the Cubs lack.

But that’s not reality. Happ holds a full no-trade clause, and by all accounts, he’s not going anywhere.

So despite the need to get creative with roster construction and the opportunity to reshape the pitching staff, the Cubs are pretty much locked in here. The bat is still competent, but the ceiling?

That’s where the doubts start to creep in.

Ben Brown, RHP: Live Arm, Short Leash

There’s no shortage of belief in Ben Brown’s tools. The fastball explodes, the breaking stuff misses bats, and when he’s locked in – particularly against the Milwaukee Brewers – he flashes upper-rotation potential. But let’s not sugarcoat it: a 5.92 ERA in 2025 won’t give opposing hitters nightmares.

Brown represents the eternal balancing act for a club like the Cubs – raw talent versus results. The front office is invested in making the experiment work, and he’ll get another crack in 2026.

But this next season isn’t just important for Brown – it feels like a make-or-break moment. If he doesn’t turn a corner, the Cubs may have to start thinking of him less like a piece of the future and more like the latest “what could’ve been.”

Eli Morgan, RHP: On the Margins but Still in the Plans

Eli Morgan’s 2025 campaign was, in plain terms, a mess. After flashing some promise with the Guardians in 2024, his stint in Chicago was marked by inconsistency and ineffectiveness. And yet, because he still holds a minor-league option for 2026, the Cubs appear poised to keep him in the mix – at least for depth.

That decision will raise eyebrows. This bullpen isn’t a luxury – it’s an area of pressing need.

Given that urgency, it’s hard to justify banking on reclamation arms like Morgan. There’s always a chance he recaptures whatever worked before, but the Cubs have to ask themselves whether their limited flexibility is best spent on projects or production.

History says they’ll bet on upside again – but the leash should be considerably shorter this time.

Dansby Swanson, SS: Defensive Wizard, Offensive Questions

Dansby Swanson may be the most polarizing name on this roster right now. He remains one of baseball’s elite defenders at shortstop – and that matters. His glove played a huge part in the Cubs slipping past the Padres in the Wild Card series, turning game-shifting plays with paralyzing consistency.

But the bat is another story. Swanson’s offensive regression isn’t just a minor dip – it’s looking more like a trend than an anomaly. His approach at the plate is starting to lag, and unless he can adjust, his bat threatens to fall below the league average for the foreseeable future.

The Cubs aren’t really in a position to ask questions about Swanson’s place on the roster – they’re committed. But that doesn’t mean they can look the other way. If the Cubs want to make a push in the next two years, they need Swanson’s glove to keep carrying elite weight – and they need his bat to at least pull its share.

Big Picture: A Contender in Limbo

So here’s where things stand: The Cubs aren’t resetting, but they’re not going all in, either. What they do have is a roster that includes a mix of declining offensive contributors, high-variance pitchers, and unmovable contracts. They have room to spend but may shy away from big moves until after the labor picture clears in 2026.

If they want to redirect the narrative and start building toward something sustainable, they’ll need internal breakouts, better health from their rotation, and an offseason that’s more savvy than splashy.

Because right now, this version of the Cubs feels stuck in no man’s land – good enough to stay afloat, but not quite built to thrive.