The Cubs are heading into an offseason with a familiar problem hanging over everything: they’re good enough to reach October, but not close enough to feel finished. Even with the possibility that Ben Brown, Justin Steele and Cade Horton might have changed the playoff picture if they’d been available, the larger issue stayed in place. Chicago still looks a step behind the Brewers, and if the Wild Card round told us anything, it’s that the Padres may have been a tougher matchup than the Cubs could handle too.
That reality is going to shape the next few months for Jed Hoyer. One of his first jobs is figuring out who should still be around in 2027, and the list is long.
Some of those decisions will come through free agency. Others will come via trade, especially with a possible work stoppage on December 1 putting a hard edge on the calendar.
Matthew Boyd is one of the clearest names on the way out. Every member of the current rotation is set to hit free agency after the World Series, and while the Cubs could have interest in bringing back a few arms, Boyd does not sound like a priority. He has helped over the last two seasons, but the Cubs do not usually chase the top of a market when regression has already started to show.
Kevin Gausman is in a similar spot, even if the fit is not quite as clean. When Chicago acquired him at the deadline, there was at least a thought he could stick around beyond this year. That idea is still alive, but his uneven run with the Cubs probably won’t lead to a fast push for a new deal.
The bullpen and depth group also looks like it will be turned over in a big way. Hunter Harvey gave the Cubs almost nothing for the money they spent, making just four appearances before a triceps injury shut him down for the year.
There’s no real path to a reunion there. Caleb Thielbar ended the season looking far closer to a DFA candidate than a trusted late-inning arm, and that makes an offseason return unlikely too.
Colin Rea’s situation says plenty about where things stand. He was a stabilizer for the pitching staff over the last two years, but by the end of the 2026 season he had been pushed into mop-up work.
That kind of usage doesn’t point to a big role ahead. Shota Imanaga is harder to pin down because his season swung so wildly, with flashes of ace-level stuff mixed with starts that forced Craig Counsell to keep a short leash.
Even so, the Cubs were not eager to commit to him long term last offseason, and that doesn’t sound like it has changed.
The catching market could pull another important name away. Carson Kelly is expected to be one of the better free agents available behind the plate, and the Cubs would likely like to keep him.
The issue is cost. They probably won’t outbid the rest of the market just to do it.
The same financial logic could apply to Ian Happ, whose future in Chicago is now tied up with Seiya Suzuki’s as both head for free agency this winter. The Cubs will need to reshape the outfield, and the sense here is that Suzuki is the preferred return while Happ is allowed to leave.
There are also several roster pieces who look more like movable parts than core answers. Gabriel Arias filled in nicely late in the year while Dansby Swanson was out, but he does not look like a 2027 bench lock. Tyler Austin never got the chance to reestablish himself after a knee injury in spring training, and it would be a mistake for the Cubs to keep paying for the hope that he can still become something more.
Matt Shaw could be headed in a different direction entirely. Chicago will need pitching this offseason and is likely to work the trade market, which could make Shaw a piece used to land a controllable starter. Tyrone Taylor is another possible return, though his market may be stronger than the Cubs want to match, especially in a thin free-agent class.
Kevin Alcantara may be on the move as well. He is out of minor-league options, and the Cubs have never seemed especially eager to hold onto him. An offseason trade as a change-of-scenery candidate feels like the likeliest outcome.
As for Michael Conforto, the Cubs will appreciate what he gave them in 2026, but with so many position players rising through the system, making his return a priority does not make much sense.
In Other News...
Pete Crow-Armstrong Just Put Cubs Fans On Notice About October
The Cubs return to the postseason ended quickly against the Padres, and the disappointment was felt most sharply among the lineups biggest names. Chicago was outscored 12-2 across the Wild Card Series, and Pete Crow-Armstrong, one of the clubs most important bats during the regular season, never found his footing at the plate while the games tightened and the margin for error disappeared.
Crow-Armstrong was blunt about his role in the setback, acknowledging that he did not contribute in October the way he had hoped after a strong year. For a young player whose growth has helped shape the Cubs outlook, the series served as an early reminder that regular-season production does not always carry over when the calendar flips, and he made clear the disappointment was as personal as it was team-wide. [Read more 🡒]
Ian Happ Just Turned A Painful Cubs Question Into A Real One
The Cubs postseason ended abruptly with a sweep by the Padres in the National League wild-card series, but the more lingering story may be what comes next for Ian Happ. The veteran outfielder has spent his entire 10-year MLB career in Chicago, and with free agency arriving this offseason, his future now sits at the center of one of the teams most emotional questions.
Happs reaction made clear this is not a routine roster decision for the Cubs or for the player. Dansby Swanson also spoke about Happs impact on the club and their friendship, underscoring how much he means inside the room as well as on the field. There is already speculation that a reunion could still happen, possibly on a hometown discount, but for now the real issue is whether one of the organizations most familiar faces is about to test a market that has suddenly made his value a real conversation. [Read more 🡒]
Cubs Never Found Momentum In A Playoff Exit Fans Will Question
The Cubs never really got the kind of clean, sustained push they needed in the wild-card round, and that left them on the wrong end of a 4-1 loss to the Padres in the clincher. San Diego completed the sweep and moved on to the National League Division Series, where it will open against the Brewers on Saturday, while Chicago was left to absorb a playoff exit that never quite found its turning point.
Nick Pivetta set the tone for the Padres, and the bullpen carried it from there, with Gavin Sheets delivering the biggest swing as a pinch-hitter with a two-run homer. For the Cubs, the frustration will linger because this was not a series defined by one meltdown so much as a failure to build momentum at any stage, the kind of postseason ending that tends to spark more questions than answers once the clubhouse empties. [Read more 🡒]