2 burning questions the Cubs must answer with the New Year underway

It's 2026, and a clear case can be made that the Chicago Cubs are worse now than they were at the end of the 2025 season. Other than Owen Caissie and Moises Ballesteros, the Cubs have no established plan to replace Kyle Tucker and have yet to address the need they have near the top of their starting rotation.

The Cubs have rebuilt their bullpen, and it's hard not to believe in their pitching infrastructure getting the most out of the veteran arms that were added. Reconstructing the bullpen was clearly the goal during the early months of the offseason, and after their latest gamble on Hunter Harvey, the other questions facing the Cubs this offseason must be answered.

2 burning questions the Cubs must answer with the New Year underway

Setting aside their work in the bullpen, the Cubs' offseason has been a failure. Again, there's reason to like each of the bullpen additions the team has made, but they may not be closer to taking the NL Central from the Milwaukee Brewers.

A path exists for the Cubs to reach that point and it will start by answering these questions.

Will the Cubs address their in the starting rotation?

The answer to this question had better be yes. The Cubs approached the trade deadline last season with a need in the rotation, and they came away with an oft-injured swingman in Michael Soroka. That failure was exposed in the playoffs.

If the Cubs weren't going to replace Kyle Tucker this offseason and they don't add a top-of-the-rotation starting pitcher, this offseason will be a failure.

The good news is that there remain several options available to the Cubs. Tatsuya Imai is the clear choice, but if the Cubs don't land him, a quick pivot to Zac Gallen may be the move.

Is this the offseason the Cubs land Alex Bregman?

It does feel like the Cubs are desperately looking for a way to add Alex Bregman to their roster this offseason. In simpler times, when the Cubs acted like the big-market team they are, they could easily sign Bregman and not think twice about it. Instead, they want the value to be exactly aligned with their long-term goals, and that is the biggest reason why they aren't at the forefront of his sweepstakes.

The hunch is that the Cubs won't land Bregman this offseason, and that is largely due to the reason that they will spend on an established starting pitcher in free agency. However, if the Cubs trade for a cost-controlled starting pitcher, they may move quickly to sign Bregman to the long-term contract that has alluded him this offseason so far.

These two questions have defined the Cubs' cautious spending this offseason. If they find a way to answer yes to just one of them, that could change the outlook of their entire winter.