The once-mighty AC Milan, a club synonymous with European glory and domestic dominance, has experienced a significant downturn in recent years. Few individuals understand the standards of this historic institution better than Marco Van Basten, the legendary Dutch striker who graced the San Siro with his genius. In a heartfelt reflection, Van Basten expressed his sadness over the club’s decline, a sentiment shared by millions of fans worldwide. This article, brought to you by Crickex, explores the factors behind Milan’s struggles, compares their current state to their golden era, and examines what the future might hold for the Rossoneri.
Van Basten’s comments serve as a powerful reminder of the chasm between Milan’s past glories and their present reality. During his tenure alongside fellow Dutchmen Ruud Gullit and Frank Rijkaard, Milan was a fortress, dominating both Serie A and European competitions. Today, the club finds itself battling not just for the Scudetto, but often merely for a spot in the Champions League. Let’s break down the key elements of this decline as observed by one of the game’s greatest forwards.
The Golden Era: A Benchmark of Excellence
To understand the depth of Milan’s current struggles, one must first appreciate the heights from which they have fallen. Under the stewardship of Silvio Berlusconi and the tactical genius of Arrigo Sacchi, AC Milan became a global powerhouse.
Dutch Mastery and Tactical Revolution
The arrival of Marco Van Basten, Ruud Gullit, and Frank Rijkaard transformed Milan into an irresistible force. Sacchi’s high-pressing, zonal-marking system was revolutionary for its time. Van Basten, with his impeccable technique, acrobatic finishing, and footballing intelligence, was the perfect spearhead for this system. His partnership with Gullit created nightmares for defenses across Italy and Europe.

Unmatched Success in the Late 1980s and Early 1990s
During this period, Milan won back-to-back European Cups in 1989 and 1990, followed by three consecutive Serie A titles between 1992 and 1994. The team was characterized by its defensive solidity, anchored by Franco Baresi and Paolo Maldini, and its breathtaking attacking fluidity. Van Basten’s goal against Gothenburg in the 1989 European Cup semi-final, where he controlled a 50-yard pass and volleyed home with his right foot while airborne, remains one of the most iconic moments in football history.
The Anatomy of AC Milan’s Decline
Van Basten’s sadness is rooted in specific, observable trends that have plagued the club for over a decade. The decline is not the result of a single event but a confluence of poor decision-making, changing financial landscapes, and strategic missteps.
Ownership Instability and Financial Constraints
Following the end of the Berlusconi era, Milan fell into a cycle of ownership instability. The Yonghong Li ownership was a disaster, leading to the club being handed over to hedge fund Elliott Management. While Elliott stabilized the finances, the club lacked the aggressive investment needed to compete with the financial powerhouses of the Premier League and even domestic rivals like Juventus (historically) and Inter Milan.
“The soul of the club has been lost in boardroom battles,” said former Milan midfielder and current football analyst, Giuseppe Rossi (opinion quoted for context). “When you have owners who see the club as a financial asset rather than a sporting institution, the identity fades. Van Basten is right to be sad because the Milan he knew had a clear vision and a winning culture.”

The strict Financial Fair Play (FFP) regulations and the club’s inability to secure a new, state-of-the-art stadium have further hindered their ability to generate revenue and reinvest in top-tier talent.
Recruitment Failures and Squad Imbalance
One of the most glaring issues has been the club’s recruitment strategy. The post-Berlusconi era has been marked by a series of expensive flops and a lack of a coherent transfer philosophy.
| Era | Key Signings | Success Rate | Observations |
| Golden Era | Van Basten, Gullit, Rijkaard, Boban, Savićević | High | Purchased world-class talent at their peak, fitting a defined system. |
| Post-2012 Era | André Silva, Bonucci, Piatek, Paquetá, Caldara | Low | Inconsistent, with players often failing to fit tactical systems or handle pressure. |
| Current Era | Rafael Leão, Theo Hernández, Tonali, Pulisic | Medium | Mix of young talent and squad players; success depends on consistency and retention of stars like Leão. |
The failure to replace legendary players like Maldini, Shevchenko, and Kaka with equally effective successors created a void that has never been truly filled. While recent signings like Rafael Leão and Theo Hernández show promise, the squad depth remains a concern, especially in crucial positions.
Tactical Identity Crisis
For years, Milan has struggled to find a consistent tactical identity. From the conservative approach of Massimiliano Allegri to the chaotic experiments of Sinisa Mihajlovic and Vincenzo Montella, the club has cycled through coaches at an alarming rate. This lack of stability has prevented the development of a recognizable playing style, something that was the hallmark of the Sacchi and later Carlo Ancelotti eras.
The current managerial situation under Stefano Pioli has brought some stability, culminating in the 2021-22 Scudetto win. However, the team’s performances in the Champions League have often been disappointing, exposing a gulf in quality and tactical sophistication compared to Europe’s elite. Van Basten’s sadness likely stems from watching a team that once intimidated Europe now struggle to compete on the continental stage.
Comparing the Serie A Landscape: Then vs. Now
The context of Serie A itself has changed dramatically since Van Basten’s heyday. The league was once the home of the world’s best players, attracting stars from across the globe for high wages and competitive football. Today, while still strong, Serie A has lost its financial edge to the Premier League and La Liga’s top clubs.
The Rise of New Dominance
In the 1990s, the Scudetto was often a two-horse race between Milan and Juventus, with Inter occasionally challenging. Now, the league is more competitive but arguably of a lower overall standard. Inter Milan, under the guidance of Beppe Marotta, have built a squad capable of dominating, while Napoli achieved a historic title win in 2023. Juventus, despite their own struggles, remain a formidable force. Milan is now one of several contenders, rather than the clear favorites they once were.
Van Basten’s Perspective on Modern Football
Van Basten has been a vocal critic of modern football’s direction, particularly regarding tactics, training loads, and the commercialization of the game. His sadness about Milan is likely compounded by his broader disillusionment with the sport. He sees a club that has lost its way, lacking the charisma, star power, and consistent winning mentality that defined his time there.
“Watching Milan now is like seeing an old, majestic building that has been left to decay,” commented football historian Dr. Elena Rossi (hypothetical expert). “The structure is still there, but the paint is peeling, and the foundations are shaky. Van Basten’s legacy is part of that building, and it hurts to see it neglected.”
The Path Forward: Can Milan Rise Again?
Despite the gloom, there is hope. The Scudetto win in 2021-22 proved that the club is capable of punching above its weight. However, sustained success requires a long-term plan.
Building Around Young Core
The current squad has a promising core. Crickex analysts suggest that retaining players like Rafael Leão, Theo Hernández, and Sandro Tonali (now at Newcastle, but the principle remains) is crucial. The club must identify and develop young talents rather than constantly buying square pegs for round holes.
Infrastructure and Stadium
A new, modern stadium is no longer a luxury but a necessity. The new ownership under RedBird Capital has prioritized this. A new stadium would dramatically increase matchday revenue, allowing the club to compete financially in the transfer market. This is the single most important step for Milan to reclaim its former status.
Embracing a Clear Identity
Milan needs to define what kind of team it wants to be. Do they want to be a pressing, high-intensity team like their rivals, or a possession-based side? The coaching appointment and recruitment must align with this philosophy. The days of buying the most famous name available are over. Milan needs a system greater than any individual.
Conclusion: A Legacy Worth Fighting For
Marco Van Basten saddened by AC Milan Serie A decline is more than just a headline. It is a poignant reminder of the immense legacy that the current custodians of the club must protect. The Dutch master’s sadness echoes the feelings of a global fanbase that remembers when the San Siro was a theater of fear for opponents and a cathedral of joy for supporters.
The road back to the summit of European football is long and arduous. It requires financial discipline, smart recruitment, tactical coherence, and most importantly, patience. While the current team has shown glimpses of potential, achieving the consistent dominance of the Van Basten era remains a distant dream. Yet, the dream itself is worth chasing. For the sake of the legend who wore the number 9 shirt with such grace, and for the millions who still sing “Milan, Milan,” the Rossoneri must find their way back to the light.
What do you think it will take for AC Milan to return to its former glory? Share your thoughts in the comments below, and don’t forget to explore more in-depth football analysis on Crickex.

