🚨 Cubs Offseason Questions: Navigating Free Agency, Trades, and Team Decisions 👇

The Chicago Cubs enter 2026 with a mix of optimism and uncertainty. While they’ve built a competitive roster with enough quality position players to field a solid lineup, there are still many decisions to be made this offseason, particularly regarding their pitching staff and key players like Nico Hoerner. The Cubs have spent time rebuilding their bullpen, but questions remain about their rotation options, the future of Hoerner, and the team’s ongoing reluctance to use deferred money in contracts.

Here’s an in-depth look at some of the biggest questions surrounding the Cubs’ offseason:

Why Does the Idea of Trading Nico Hoerner Keep Coming Up?

One of the most baffling and persistent rumors surrounding the Chicago Cubs this offseason has been the idea of trading Nico Hoerner. While fans and players alike have expressed disbelief over this topic, the reality is that Hoerner’s contract expires after this season. The Cubs’ front office is known for valuing pre-arbitration players and finding the best value in trade discussions. In a system where no player is off-limits, the potential for a trade becomes more likely when a player is approaching free agency, especially if they’re coming off a career-high season, as Hoerner is.

Hoerner’s defense, base-running ability, and high-contact hitting make him an incredibly valuable asset to the Cubs. However, his lack of power keeps him from being viewed as a true star, which slightly diminishes his trade value despite his impressive all-around skills. With Hoerner’s WAR at 4.8 in 2025, the Cubs may see this as the perfect time to trade him at his highest value, but the chances of him being traded remain low unless the Cubs make a major move and bring in another player like Alex Bregman.

Why is the Cubs Organization Against Deferred Money?

The Cubs have been somewhat resistant to using deferred money as part of their financial strategy, especially when compared to other teams in big markets. Deferred money, used by teams like the Los Angeles Dodgers to secure deals for players like Shohei Ohtani, has been instrumental for some teams in making big signings without taking a massive immediate financial hit. The Cubs, however, have a conservative approach to team-building and ownership prefers maintaining flexibility for future seasons.

While the Cubs have used deferred money in the past, notably with Jon Lester and Jason Heyward during their World Series run in 2016, their post-championship approach focuses on sustainability rather than going all-in for one season. The Cubs want to avoid taking away resources from future teams, which could explain why they’ve avoided the heavy use of deferred contracts that some other top franchises have embraced.

The Cubs’ Bench Construction: What’s the Plan?

With the potential for Matt Shaw to take on a super-utility role, the Cubs are working to bolster their bench for the 2026 season. The Cubs are already looking at a few low-cost options to strengthen their roster, such as adding Tyler Austin, a former Yankees player who spent the past few years playing in Japan. Austin posted an .834 OPS with the Yokohama BayStars in 2025 and could provide some depth as a right-handed hitter off the bench.

The Cubs are also considering three catchers for their Opening Day roster, given their glut of young position players at the Triple-A level. Players like Willi Castro and Rob Refsnyder—who was recently signed by the Seattle Mariners—have been floated as potential bench pieces, but the challenge remains in recruiting bench players who will accept limited playing time and are not guaranteed regular at-bats.

What Happened to Kevin Alcántara, and What’s His Role in 2026?

Kevin Alcántara, once considered a top-100 prospect, had a bit of a setback in 2025 due to core surgery. It’s unclear how much that injury held him back during the season, but he is expected to be fully recovered by spring training in 2026. Alcántara has always been known for his defensive ability, particularly in center field, where he is at least an average defender and possibly a plus one.

His offensive potential is immense, but Alcántara has been inconsistent, and his lack of playing time in 2025 is a reflection of the Cubs’ relatively healthy outfield and their focus on Pete Crow-Armstrong and Ian Happ. Alcántara will need to find consistency in his game to have a chance to contribute in the majors, but whether that’s with the Cubs or in a trade remains an open question.

Could the Cubs Be in the Running for Tyler Glasnow?

The Cubs were reportedly involved in trade talks for Tyler Glasnow before the Tampa Bay Rays agreed to send him to the Los Angeles Dodgers in a five-year, $136.5 million contract extension. The Cubs have shown interest in adding a frontline starting pitcher, but they’re reluctant to give up top prospects like Jaxon Wiggins or Cade Horton. The team faces a dilemma: how to improve their rotation without parting with their elite young talent.

While the Cubs have reportedly discussed Ian Happ in potential trades for starting pitchers, Happ’s no-trade clause makes it unlikely he would be dealt. However, if the Cubs are serious about landing a star pitcher, they will have to balance long-term growth with immediate needs.

Jaxon Wiggins: Is He Ready for the Big League Stage?

The Cubs are high on Jaxon Wiggins and see him as a potential contributor in 2026. However, the most likely scenario is for Wiggins to start the season in the minors and continue to develop before making an appearance in the major leagues. The Cubs are looking for opportunities to add depth in the rotation and bullpen, and if Wiggins stays healthy and improves his command, he could earn a role as a valuable piece of the pitching staff.

The Future of Pete Crow-Armstrong: A Long-Term Cubs Star?

Pete Crow-Armstrong remains the Cubs’ most valuable asset, and long-term contract discussions are expected to ramp up in the near future. Crow-Armstrong’s development as a Gold Glove-caliber center fielder and offensive weapon makes him the face of the franchise moving forward. His potential to be with the Cubs for the next decade has the front office engaged in contract talks, and the team is keen on locking him down for the long haul.

As Crow-Armstrong continues to develop into one of the top young players in baseball, the Cubs will look to extend him before he becomes a free agent in 2030. He could very well be the centerpiece of the team for many years to come.

Conclusion: A Critical Offseason for the Cubs

As the Cubs head into 2026, the team faces critical decisions on the roster, trade market, and young talent development. While the Cubs have shown a willingness to make moves in free agency and trades, they’ve also been cautious about taking risks that could affect the team’s future flexibility.

With a potential big splash still on the horizon, the Cubs’ offseason is far from over. Whether it’s landing a key free agent like Alex Bregman or making a trade for a frontline pitcher, the front office will need to balance immediate improvement with the long-term health of the organization. The next few months will determine whether the Cubs can take the next step toward contention or whether they’ll need to reevaluate their approach.