The Chicago Cubs are the third largest market in Major League Baseball. Yet, their performance and financial investments don’t seem to match up to their advantage. Compared to teams like the New York Yankees and Los Angeles Dodgers, who regularly sign top players and lead in salary spending rankings. The Cubs seem to be caught in a cycle of performance due to the team’s ownership being cautious with money and questionable moves made by their management team.

The Ricketts family, who owns the Cubs, has faced growing criticism for their unwillingness to push payroll to competitive heights. Despite the financial windfall of a massive market, the Cubs frequently operate below expectations for a franchise of their stature. Even after shedding significant salaries during their rebuild, they haven’t reinvested at the level fans anticipate. Even now, after years of restructuring, the Cubs operate with a payroll that pales in comparison to their market peers.

Star power deficiency: The Chicago Cubs’ identity crisis

According to ESPN’s Jesse Rogers, in the aftermath of a blockbuster Kyle Tucker trade, the Chicago Cubs let Cody Bellinger walk away, leaving the fans with disappointment. One agent sarcastically commented, “I guess this is the Cubs’ version of going all-in.” Under Jed Hoyer’s leadership as the President of Baseball Operations following Theo Epstein’s exit, it has been frustrating for the Cubs. They have failed to make it to the playoffs for two years in a row despite having resources at their disposal. Hoyer’s moves often generate more questions than confidence.

For example, he traded for Kyle Tucker, a bonafide star, but simultaneously allowed Cody Bellinger to leave. While Tucker bolsters the offense, Bellinger’s departure highlights the Chicago Cubs’ inability to retain key contributors. The front office also struggled to address glaring needs. They failed to land a top-tier catcher despite the position ranking near the bottom of the league in production last season. Their rotation lacks an ace, and their bullpen issues—exposed in 2024—remain unresolved.

These failures contribute to a pattern of unfulfilled promises, frustrating fans expecting more from one of baseball’s marquee franchises. For the Cubs to reclaim their status as perennial contenders, they need a culture shift—both in spending and roster-building. Until ownership and the front office align their vision with the expectations of a large-market powerhouse, mediocrity may continue to define Chicago’s north side.

A hollow rebuild, where did the money go?

The Chicago Cubs embarked on a rebuilding journey after disassembling their championship-winning core in 2016 with the vision of a future driven by flexibility and emerging talent in the team’s roster. Key players like Kris Bryant and Anthony Rizzo were traded for promising prospects, while payroll adjustments were made to pave the way for strategic reinvestment efforts. However, the anticipated spending spree did not quite materialize as expected.

Although the Cubs made acquisitions such as Marcus Stroman and Dansby Swanson during this period. They fell short in pursuing top-tier free agents who could potentially propel the team to contender status. In contrast to what’s typically anticipated for a team in the third-largest MLB market, this emphasis on cost-effectiveness is quite surprising. Adding to the disappointment, the Chicago Cubs’ investments during the rebuild have delivered inconsistent returns—financial commitments lingered on underperforming veterans like Jason Heyward, while attempts to rebuild through trades yielded only partial success.

Though prospects like Pete Crow-Armstrong offer hope, the team has struggled to develop a pipeline of contributors ready to make an immediate impact. As payroll savings from the rebuild remain underutilized, glaring roster holes—such as at catcher and in the bullpen—continue to hinder the team’s ability to compete. Without significant reinvestment and bold decision-making, the rebuild risks becoming a hollow exercise rather than the foundation for sustained success.

To break free from mediocrity, the organization must align ownership’s resources with bold, strategic decisions that address critical roster needs and rekindle fan confidence. Do you feel that without urgent action, the gap between the team’s promise and performance will only grow wider? Share your take in the comments.