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AC Milan: The Fall of a Giant

In the mid-2000s, AC Milan was one of Europe's biggest teams. Almost 20 years later, they are merely mediocre. How did this happen?

AC Milan: The Fall of a Giant Photo: © IMAGO/Colorsport/Insidefoto/KI
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On May 23, 2007, AC Milan ascended the throne of European football. 

Thanks to a brace from Filippo Inzaghi, the Carlo Ancelotti-coached "Rossoneri" won the Champions League final against Liverpool 2-1. 

This marked the seventh time in the club's history that the squad, featuring players like Kaka, Paolo Maldini, and Andrea Pirlo, lifted the coveted trophy. At the same time, the Milanese got their revenge for the legendary Istanbul final, where they squandered a 3-0 half-time lead against the "Reds".

But while Milan was one of Europe's most dominant teams in the mid-2000s, the 2007 triumph also marked the end of an era.

Now, almost 20 years after their last victory in the Champions League, Milan will face FC Salzburg in the Europa League on Thursday (6:45 PM CET in the LIVE ticker>>>).

Although the seven-time Champions League winner remains one of European football's big names, the club is far from its former supremacy in terms of sporting performance.

First Rebuilding Proved Successful

At the time of the 2007 triumph, several key "Rossoneri" players were actually at their peak or had already passed it.

Nevertheless, a successful transition initially followed. With new players like Thiago Silva, Kevin-Prince Boateng, and Zlatan Ibrahimovic, the Milanese managed to clinch the Scudetto once again in the 2010/11 season.

Yet, Milan's creeping decline still began, primarily linked to an individual who wasn't on the field: Silvio Berlusconi.

Berlusconi's Sporting Revolution

Berlusconi's Sporting Revolution
Marco van Basten, Arrigo Sacchi, Franco Baresi, Silvio Berlusconi, Frank Rijkaard und Ruud Gullit
Foto: ©imago / Buzzi

"It was Berlusconi's AC Milan. He was a true revolutionary who changed the rules of the game through entrepreneurial management of the club and turned football into a spectacle," says Italian journalist Valentino Beccari to LAOLA1.

Berlusconi, who passed away in June 2023, first took over the club in 1986 and led it as president until 2004, and again from 2006 to 2008. Under his leadership, the Rossoneri experienced their most successful period. Milan won seven league titles and five Champions League titles under Berlusconi.

Alongside the mid-2000s, the late 1980s era was a golden age for AC Milan. On the pitch, this period was shaped by the three Dutch "Tulips."

"The idea was to sign three exceptional Dutch players like Ruud Gullit, Marco van Basten, and Frank Rijkaard and to rely on a visionary coach like Arrigo Sacchi, who introduced pressing, the extreme offside trap, and interchangeability of roles," says Beccari.

"Things were much simpler with Berlusconi"

Under Berlusconi, Milan not only had sporting prowess but also the financial clout to compete with Europe's top teams. 

Beccari comments: "With Berlusconi, many things were simpler, also because he personally intervened to increase the club's capital. This gave Milan more leverage in the transfer market."

Investmentfonds wollen natürlich mit dem Fußball Geld verdienen. Deshalb steht die Gewinnlogik über allem.

Valentino Beccari

Although the "Rossoneri" celebrated countless successes under the former Italian Prime Minister, problems eventually arose. While he stepped down as president in 2008, he remained deeply rooted in the club as honorary president even after that. 

Sportingly, the club increasingly stagnated in the 2010s. After winning the championship in 2011, the club slid further and further into Italian mediocrity season after season. In 2015, the club finished a season outside a single-digit league position for the first time in the new millennium.

Complicated Takeover

Two years later, the Berlusconi era at Milan finally came to an end. The sale of the club in 2017 was meant to enable a fresh start. Berlusconi's holding company Fininvest handed over Milan to Chinese businessman Yonghong Li. The purchase price was around 740 million Euros, but the financing of the takeover caused significant controversy.

Already in 2018, the US investment fund Elliott Management took control of the club after Li was no longer able to meet his financial obligations. This marked the beginning of another phase of upheaval for Milan.

A report from the Italian sports newspaper "La Gazzetta dello Sport" in January 2020 illustrated how little the substantial investments initially achieved. According to the report, Milan had spent approximately 467 million Euros within about 30 months without making significant sporting progress. Elliott alone had invested almost 240 million Euros of that.

At the same time, coaches and executives changed frequently, while a clear sporting direction was difficult to discern.

The Market Dictates the Rules

The Market Dictates the Rules
Foto: ©IMAGO / Buzzi

The problem, therefore, wasn't simply that Milan had too little money available. Rather, the club failed to convert its expenditures into sustainable sporting success. New players were supposed to enable the next step, but the team fell short of expectations.

For Beccari, the transition from Berlusconi to investment funds marks a crucial turning point.

"Milan's decline began with the end of the Berlusconi era and the transition to investment funds," explains the journalist. 

With them, the economic orientation also changed. Instead of personal capital injections, financial sustainability increasingly became the focus. "With the advent of investment funds, the market dictated the rules. The club now finds it difficult to spend more than it earns," says Beccari.

Profit Maximization

Under Elliott, financial stabilization became the central task. The club had to control its costs, improve revenues, and solidify its economic foundation. At the same time, Milan was expected to rebuild a competitive team.

A key component of this strategy was the signing of young players whose market value was to be increased through sporting development. With suitable offers, they could later be sold for a profit.

Der Meistertitel von 2022 hätte der Beginn eines neuen Zyklus sein können.

Valentino Beccari

Beccari sees a fundamental risk in this: "Investment funds naturally want to make money from football. Therefore, profit logic takes precedence over everything."

The so-called 'trading model' is widespread in modern football and can certainly be successful. However, it requires a club to identify talents early, correctly assess their development, and integrate them into a functioning team.

"This model necessitates a strong scouting network and does not allow for many mistakes," warns Beccari.

Maldini, Massara and Pioli

Maldini, Massara and Pioli
Frederic Massara, Stefano Pioli und Paolo Maldini
Foto: ©imago images / LaPresse

Despite criticism of the new investor group, things started looking up again for the "Rossoneri" from 2019. With Frederic Massara as Sporting Director, Paolo Maldini as Technical Director, and Stefano Pioli as coach, three crucial figures were installed. 

In 2021, Milan became vice-champions, finishing a season in a Champions League spot for the first time in eight years. In the following season, they achieved the ultimate success: Milan won the Scudetto again for the first time since 2011.

"The 2022 championship title could have been the beginning of a new cycle – with an experienced coach like Pioli, two reliable executives like Maldini and Massara, and high-calibre players like Rafael Leao, Theo Hernandez, and Mike Maignan. But then the club decided to replace the management, thus taking a step backward," says Beccari.

In the following season, Pioli's team sensationally reached the Champions League semi-finals, where they had to concede defeat to city rivals Inter. Despite this, Maldini and Massara still had to leave at the end of the season.

Expensive Flops

Expensive Flops
Goncalo Ramos und Diego Moreira
Foto: ©IMAGO / Gribaudi / ImagePhoto

For Beccari, this was a clear misjudgment: "In my opinion, it was a serious mistake to dismiss two football operations executives like Maldini and Massara and instead rely on Ibrahimovic, who lacked the necessary experience."

In recent seasons, Milan has consistently invested over 100 million Euros in new transfers, yet the new transfer strategy hasn't truly paid off. Stars like Theo Hernandez and Rafael Leao were sold below market value, and new signings – especially offensive players – mostly turned out to be flops.

This summer, the "Rossoneri" signed Diego Moreira and Gonçalo Ramos, their record acquisitions to date. Ramos, in particular, has been struggling with considerable initial difficulties. The Portuguese, who moved from Paris to Milan for 74 million Euros, has only scored one goal so far.

Inconsistency has also plagued the coaching bench since Pioli's departure. The current coach, Ruben Amorim, is already the fourth coach within two years.

Long-term Plan

For Beccari, it is therefore clear what needs to change: "Managers must be found who understand football better than finance."

The 2022 Scudetto showed that Milan can win titles again even under changed conditions. With Maldini, Massara, and Pioli, the club had found a setup that was successful on the pitch. The fact that this was dismantled after the greatest success in recent club history is emblematic of the "Rossoneri's" problem.

The path back to the top therefore does not lead solely through expensive new signings or the next high-profile coach. The decisive factor will be whether Milan finally develops a sporting vision that those in charge will adhere to long-term.

UEFA Europa League: FC Salzburg - AC Milan, Thursday, from 6:45 PM CET in the LIVE ticker >>>

VIDEO: They played for Inter and AC Milan

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You can find the original LAOLA1 article here.