The Chicago Cubs are on the Verge of Making a Major Mistake in Team Building

The Chicago Cubs may be making a critical error in roster planning and unfortunately, the timing could not be worse. In baseball, whether a team is rebuilding or on the brink of contention, one principle holds: bold moves often outweigh cautious ones.

Long-term, high-value free-agent deals can backfire over time, yes. But championship windows are fleeting, and when a team is close to competing for a World Series, leaving money on the table is rarely wise. Such contracts can occasionally create bottlenecks in player development, but contenders prioritize proven talent, depth, and roster flexibility, even if it temporarily limits opportunities for top prospects.

Too often, MLB teams let fear of a contracts downside block their actual potential. They prioritize development schedules over maximizing the current playoff window. Unfortunately, the Cubs appear to be falling into this exact trap.

After winning 92 games in 2025 and remaining competitive throughout the season, the Cubs still fell short, finishing five games behind the Milwaukee Brewers in the NL Central. They won the Wild Card Series against San Diego but were eliminated by Milwaukee in the NLDS, losing 32 in the first postseason clash between the rivals. That should have been a clear signal: Milwaukee had the edge, and the Dodgers remain the benchmark for excellence.

Looking toward 2026, the road to a World Series for Chicago is challenging. Complicating matters, Kyle Tucker the Cubs third-most valuable player in 2025 became a free agent, and the team showed little interest in matching his anticipated contract. He is likely to sign with a strong National League team, possibly the Dodgers, further widening the gap between Chicago and contention.

Analysts widely agree that while re-signing Tucker wasnt strictly necessary, the Cubs should have redirected those funds toward multiple impactful acquisitions. For example, pairing a frontline starter like Dylan Cease with a middle-of-the-order bat such as Kyle Schwarber would cost roughly the same as Tuckers expected deal, while improving the team on two fronts. Yet, this appears not to be the plan.

Reports indicate the Cubs intend to give top prospects Owen Caissie and Moiss Ballesteros significant playing time in 2026. This approach emphasizes development, regular at-bats, and tolerance for mistakes a strategy that may cost games and is at odds with a team primed for a championship run.

Patrick Mooney of The Athletic wrote: Cubs officials will continue working on their plans to replace Tucker, reallocating resources to different parts of the roster, utilizing Seiya Suzuki more in right field, and creating the runway for young hitters Owen Caissie and Moiss Ballesteros to develop and improve at the major-league level. During this period before next weeks Winter Meetings, Jed Hoyers front office remains focused on adding to the pitching staff in quantity and quality.

While prioritizing pitching is sensible, the offense faces setbacks without Tucker, arguably the teams best hitter. The current roster is not stronger than it was at the end of 2025, and assuming otherwise is optimistic.

The Cubs have developed their core Justin Steele, Cade Horton, Matt Shaw, and Pete Crow-Armstrong and unearthed valuable talents like Michael Busch. That stage of development is largely complete; now is the moment to push for victory, not delay.

Instead of capitalizing on a strong 92-win foundation, the Cubs are emphasizing player development while other teams are acting aggressively. Financial constraints may explain Jed Hoyers cautious approach, with resources focused on pitching. However, ownership needs to provide the additional investment required to transform the team into a World Series contender. Right now, fans are being asked to accept patience when bold action is needed, and unless this approach changes, the Cubs may drift further from a championship rather than toward it in 2026.

Author: Sophia Brooks