Silvio Berlusconi: A Complicated Legacy in Italian Football

“He is talented, intelligent, kind, and capable of inspiring our players,” remarked the club president. “To enhance their motivation, I informed them, ‘You will face teams like Milan and Juventus, so if you manage to defeat one of these giants, I’ll arrange for a celebratory welcome in the locker room with a bus full of women!’

This was emblematic of Berlusconi, and his so-called ‘joke’ elicited laughter in the room. However, when a video of the speech circulated online, many Italians—who have long viewed Berlusconi as a national embarrassment—failed to find humor in it.

This reaction was not surprising. The media mogul remained a deeply divisive figure throughout the country. Despite a political career marred by scandal, Berlusconi secured a Senate seat in 2022, with his Forza Italia party becoming a crucial element in the newly formed right-wing coalition government led by Giorgia Meloni.

What remains indisputable is that Berlusconi made significant historical contributions to football, repeatedly making headlines first with AC Milan and later with Monza.

Interestingly, Berlusconi frequently expressed that his efforts went unacknowledged, particularly concerning AC Milan. In 2004, he lamented, “People talk about the Milan of [Arrigo] Sacchi, [Alberto] Zaccheroni, and [Carlo] Ancelotti, yet I, who have spent 18 years selecting the team, creating the rules, and acquiring players, am often overlooked! It feels as if I do not exist!”

However, both Berlusconi and his impact on Italian football were impossible to ignore. He revitalized Serie A’s dormant giant. When Berlusconi took over AC Milan in 1986, the club was on the brink of collapse, and he deserves substantial credit for its turnaround, as Milan was not particularly appealing at that time.

“The financial situation of Milan would have discouraged anyone,” he remarked shortly after acquiring the club. “Even now, there are gaps in the accounts yet to be addressed, and the total debt remains unclear, but there was no other choice.

“On one side, there was a Milan exposed to dire circumstances—bankruptcy, liquidation, and legal battles. On the other, there was Berlusconi the fan, unwilling to witness such a tragedy. At that moment, my heart took over, making the decision to purchase Milan unavoidable.”

It was a gamble that yielded remarkable results, courtesy of Berlusconi and his right-hand man, Adriano Galliani. In just three years, they assembled arguably the finest team in club football history.

“According to a FIFA vote, Arrigo Sacchi’s Milan played the most beautiful football ever. It’s hard to articulate, but witnessing that team play was an unparalleled experience,” Berlusconi reflected in an interview with Gazzetta dello Sport.

“I’m grateful that my father, who guided me through the highs and lows of supporting Milan since my childhood, lived to witness it.”

Sacchi’s team was indeed a pleasure to watch, featuring a historically transformative squad that boasted a brilliant Italian defense and a trio of Dutch superstars: Marco van Basten, Frank Rijkaard, and Ruud Gullit.

Appointing Sacchi was pivotal—another high-stakes decision that turned out to be a masterstroke. With only one title to his name—the Serie C1 title—his arrival at San Siro was met with skepticism and disbelief. Many influential media figures were aghast that the responsibility of rejuvenating Milan was entrusted to a coach lacking experience at the highest level.

Sacchi famously responded to doubts regarding his qualifications by quipping, “I never realized that to become a jockey, one must have been a horse first.”

Under Sacchi’s leadership, Milan secured eight trophies, including back-to-back European Cups, while playing a revolutionary style of football. As Berlusconi noted, it was the most beautiful beginning to an “epic” empire that established him as the most decorated president in club football history.

It’s hardly surprising, then, that he came to consider himself a tactical expert. Over his three-decade tenure, there were numerous reports and allegations regarding his interference in team selections. At one point, he even declared that “any Milan coach must field at least two strikers. This isn’t a request; it’s a mandate.”

In that context, Ancelotti’s eight-season tenure at San Siro is nothing short of remarkable. He had to contend not only with a president who questioned his formations and selections but also endured lighthearted jabs at his weight!

By the conclusion of Ancelotti’s time at Milan, it became increasingly clear that Berlusconi was no longer in a position to continuously invest in the club. In 2009, he even addressed rumors of a potential sale but, in his characteristic self-aggrandizing manner, claimed he had yet to find a buyer who would “benefit the club more than I do.”

What ensued was a gradual, yet noticeable, reduction in spending. Milan clinched the league title in 2010-11 but subsequently lost key players Zlatan Ibrahimovic and Thiago Silva to Paris Saint-Germain the following year—an unmistakable signal that Berlusconi could no longer compete with the sport’s nouveau riche. Ultimately, when he departed from the club in 2017, he lamented that “competing at the highest level in modern football requires investments and resources that a single family can no longer sustain.”

And that seemed to be the end of his footballing journey. At 80 years old and still actively engaged in Italian politics, Berlusconi surprised many by returning just over a year later, persuaded to buy AC Monza by his long-time friend and trusted advisor, Galliani.

The potential of Monza was undeniable. Situated in one of northern Italy’s most industrious regions, home to a famous Formula 1 racetrack and close to the bustling city of Milan, Monza had previously attracted numerous ambitious investors. However, unlike others, Berlusconi succeeded spectacularly, leading Monza from Serie C to Serie A in just four seasons—an incredible feat considering they had never before competed in Italy’s top tier.

“It’s remarkable for a club like Monza, established in 1912, to achieve promotion after 110 years,” Berlusconi stated following the playoff final win against Pisa in 2022. “Now that we are in Serie A, we must aim for the Scudetto and strive to conquer the Champions League as well. I’m accustomed to winning, so let’s see…”

While Monza may not have reached the ambitious heights Berlusconi envisioned, he lived to witness the club’s victories over Juventus twice in their inaugural season, finishing 11th in Serie A, and he proudly recognized the infrastructure he established to support the Biancorossi’s future success.

“We expanded our training facility, Monzello, which is now the largest and most impressive in Italy,” Berlusconi emphasized. “We also improved the stadium with a modest investment of €25 million (£22m/$27m). Things have changed: when we arrived, there were 300 spectators attending Monza’s matches; now, we see 10,000.”

Berlusconi’s passing was a significant loss for Monza, who faced relegation in 2025—just two years after the death of their controversial yet charismatic benefactor, whose legendary status played a crucial role in attracting players to the club.

As success stories go, Monza’s brief ascent might not quite match Berlusconi’s remarkable transformation of Milan from the brink of bankruptcy to global domination, but it remains another impressive achievement in the highly competitive realm of football.

Unsurprisingly, his death sparked debate throughout Italy, largely concerning whether he had done more harm than good over his lifetime. He certainly wasn’t mourned by many women or leftists. If he did find himself in heaven, he might have faced a few disgruntled angels upon his arrival. Regardless, he undeniably served as an extraordinary president for both Milan and Monza.