The Chicago Cubs are one of the most storied franchises in Major League Baseball history. The team’s fan base has witnessed highs and lows, but perhaps no event has marked the franchise more than the century-long drought between World Series championships.
After finally breaking the infamous 108-year curse in 2016, the Cubs gave their loyal fans a taste of what it feels like to see the ultimate triumph.
Yet as the years have passed since that magical moment, the Cubs have found themselves struggling to reclaim that level of success.
In fact, some might argue that they are repeating the same mistakes that contributed to the prolonged drought in the first place.
The 2016 Championship: A Flash in the Pan or Sustainable Success?
The Cubs’ 2016 World Series victory remains a beacon of hope for fans. The team’s dynamic roster, featuring the likes of Kris Bryant, Anthony Rizzo, and Jake Arrieta, brought a level of excitement not seen in decades.
Under manager Joe Maddon, the Cubs blended a strong blend of analytics with an emphasis on player development, leading to a perfect storm of success that culminated in the team’s first championship in 108 years.
However, the euphoria of 2016 has been tempered by a sense of disappointment in the years that followed.
The Cubs’ front office, led by president of baseball operations Theo Epstein, built the team on a foundation of solid scouting and player development. But as is often the case in baseball, success can be fleeting.
Since their 2016 triumph, the Cubs have struggled to replicate the same level of success, and many of the key players from that championship squad have seen their performance decline.
This leads to the question: Is the Cubs’ franchise repeating past mistakes, or is the nature of the sport simply a cruel reminder of how difficult it is to sustain success in Major League Baseball?
The Player Development Dilemma
One of the pillars of the Cubs’ 2016 championship was their emphasis on player development.
From the scouting of future stars like Bryant and Javier Báez to their focus on building an analytics-driven system, the Cubs built a model that was widely lauded for its forward-thinking approach.
However, in the years following the championship, the team failed to continuously develop young talent to replenish its roster.
The Cubs’ inability to adequately replace aging stars or develop the next wave of talent has been a significant issue.
While they have managed to remain competitive in some seasons, the lack of sustained player development has become glaring. The team has found itself in an awkward position, with an aging core and limited future impact players in the minor leagues.
As the Cubs’ championship-caliber stars began to decline or leave via free agency, the team was left without the necessary pipeline of talent to maintain a high level of performance.
This brings to mind the Cubs’ past mistakes, particularly during the decades leading up to their 2016 victory. For much of their history, the franchise struggled with poor drafts and inconsistent player development.
While the front office has attempted to improve in this area, the Cubs are once again facing questions about their ability to sustain success by developing homegrown talent.
Relying Too Heavily on Expensive Veterans
In addition to its struggles with player development, the Cubs’ roster construction has raised concerns.
One of the key issues has been their reliance on expensive veterans, often at the cost of investing in younger, more cost-effective players.
In an era of baseball where financial flexibility is more important than ever, the Cubs have frequently handed out big contracts to aging stars, hoping that their experience and leadership will guide the team to victory.
This reliance on veteran players has placed the Cubs in a precarious position. While veterans like Rizzo, Báez, and Bryant once represented the core of a championship-caliber team, they have increasingly struggled to produce at a high level.
In contrast, other MLB teams have focused on cultivating young, cost-controlled talent and improving their farm systems, giving them an edge in roster construction.
Moreover, the Cubs’ willingness to commit significant financial resources to players who may no longer be at their peak raises the question of whether the organization is repeating the mistakes of its past.
In earlier decades, the Cubs often failed to recognize when it was time to rebuild or part ways with aging players, which delayed their chances of success.
If the Cubs are not careful, they could be repeating the same errors of over-committing to veterans past their prime.
The Future: A Crossroads for the Cubs
As of 2025, the Cubs find themselves at a crossroads. The team has a strong fan base that expects more than just occasional playoff appearances.
The franchise must go through a competitive landscape that includes not only established powerhouses but also emerging teams that have adopted a more aggressive approach to team building.
While the Cubs’ front office has made some notable moves in recent years, they are facing a significant challenge: balancing the need to stay competitive while simultaneously rebuilding the core of the team.
The Cubs have a choice to make. They can continue to pour resources into their aging roster and hope that a few more stars can lift them to championship contention, or they can look toward the future, investing in youth, analytics, and player development to build a sustainable championship contender for years to come.
Ultimately, the Chicago Cubs are at risk of repeating the same mistakes that plagued them in their lengthy World Series drought if they do not adjust their approach.
To avoid falling back into mediocrity, they must learn from their past and focus on long-term success over short-term fixes. Whether or not they can capitalize on the lessons of their past remains to be seen, but for the Cubs, the future is now.
