Chelsea’s Season of Contradictions: Cup Final Appearance Masks Deeper Concerns
Chelsea’s path to the Carabao Cup final has provided something rare in their 2023–24 season: a clear, upward moment. Mauricio Pochettino’s side saw off Middlesbrough with an emphatic semi-final second leg, booking a trip to Wembley that will offer a chance at silverware and, perhaps more importantly, a moment of clarity in an otherwise confusing campaign.
Yet for all the celebration that greeted the final whistle, Chelsea’s broader picture remains difficult to decipher. Sitting mid-table in the Premier League, far from European contention, and with continued uncertainty in performance and personnel, it is hard to tell whether the club is building or simply treading water.
The final itself will not answer every question. But it may shape the way this season is remembered—and whether it becomes the foundation for something stable or yet another footnote in a prolonged transition.
Pochettino’s Balancing Act
Mauricio Pochettino arrived at Stamford Bridge tasked with more than just improving results. He was expected to stabilise a young and expensive squad, instil identity, and bring order to a club that had undergone significant change post-Abramovich. The promise was not immediate success, but visible structure.
So far, that structure remains elusive.
Chelsea’s form has veered between spirited and static. Wins have come, but rarely with the authority or consistency that suggests a team on the rise. In some matches—particularly cup outings—the team has shown purpose and cohesion. But in the league, old habits reappear. Defensive lapses, midfield imbalances, and a lack of composure in the final third continue to undermine progress.
Pochettino, to his credit, has remained composed. He has spoken of patience, of trusting the process. But around him, both fans and pundits have begun to question whether the manager’s influence is translating into real development.
Youth, Promise, and the Price of Inexperience
One of the defining characteristics of Chelsea’s new era is its youth. The club’s investment in players under 23 has been bold, even unprecedented. Cole Palmer, Enzo Fernández, Moisés Caicedo, and Benoît Badiashile are all seen as long-term pillars.
But with youth comes volatility. The performances have been energetic but often naive. Game management has faltered under pressure. Mistakes, particularly at the back, have cost points that more seasoned sides would have closed out.
The talent is not in doubt. The question is whether the current environment is helping it flourish. With few experienced leaders in the dressing room and no stable spine, the team often plays like what it is: a high-potential group still learning how to compete at the top level.
Ownership and Expectations
Above the pitch, Chelsea’s ownership continues to cast a long shadow over football operations. The Todd Boehly-led consortium’s approach to recruitment and structure has been ambitious but unorthodox. Sporting directors have come and gone. Contracts have been lengthened, transfer strategies widened. Yet results on the field have not caught up with the planning off it.
Supporters, once willing to buy into a long-term project, are beginning to show signs of fatigue. The club that once measured success in trophies is now being asked to measure it in potential. For many, that is a difficult adjustment.
A Final with Real Implications
Should Chelsea defeat Liverpool in the Carabao Cup final, it would provide more than silverware. It would offer Pochettino something to build on—a tangible success to point to amid mixed results. It could also lift the mood in the dressing room and affirm belief in the broader direction.
But failure to capitalise would reopen the same debates. What is Chelsea’s identity? Is the squad balanced? And perhaps most crucially—what does progress actually look like under this regime?
The Carabao Cup may not be the club’s ultimate ambition, but in a season short on clear victories, it now carries weight.
Not just for the record books—but for the narrative of what Chelsea are becoming.