On a rainy Friday morning in July 1986, 10,000 bewildered and hopeful Milan supporters gathered at the Arena Civica, a small training field in the center of Milano, to get introduced to their new President and the roster for the upcoming season. They didn’t know what to expect.
Out of nowhere, three helicopters suddenly appeared in the grey sky and came fluttering along, the roar of their rotor blades mixed with the loud music coming from some strategically placed loudspeakers pumping Richard Wagner’s Ride of The Valkyries. It was like being in Apocalypse Now.
The helicopters landed on the pitch, and the players theatrically emerged from them one by one while the crowd erupted in wild chants. And then, lastly, he appeared. Silvio Berlusconi. The new President of Milan. No, the Rossoneri fans didn’t know what to expect. But you can tell a good day from the morning, even a rainy one.
Much can be said about Silvio Berlusconi, who passed away on Monday at 86 years of age. Arguably the most controversial and polarizing character in Italy in the last 40 years, he lived one and many lives, journeying through multiple entrepreneurial adventures as a real estate constructor, a broadcaster, a politician (to date, he is the country’s longest-serving Prime Minister), and, of course, a football club owner.
And, since a whole book wouldn’t be enough to encompass the life and tales of this Very Italian Person, one that truly epitomized and amplified the vices and virtues of the average Italiano, here we will only focus on his days as a football president, first of Milan and then, more recently, of Monza.
Because one may have loved him or hated him, but there is no denying that Berlusconi has changed the way a football club operates at a global level, making the whole game transition to a truly modern era. For good or for bad.
Before the American investment funds, before the Asian, Russian, Middle Eastern magnates would start splashing some cash in the beautiful game, before the players would understand they could be influential stars with a global outreach and start acting accordingly, there was this man who understood that a football club must be structured and managed like a corporate company. It seems obvious nowadays, but that was not the case in the mid-1980s.
Back in the days, the roster of an average football team was made of 11 undisputed starters, an experienced backup goalkeeper, two-three versatile substitutes, and a couple of home-grown youngsters. That was it.
With his “invincible” Milan, Berlusconi was the first to theorize and make the concept of squad rotation possible, ensuring the good Fabio Capello had at least two – if not three – potential starters in each role. He did so by not hesitating to mercilessly pillage and plunder the transfer market, bringing to Milanello any player that came under his radar like your average Nasser Al-Khelaifi would do.
Did all this do any good to football? Only time will tell. But one thing is for sure: There would not have been any Roman Abramovic or Tedd Boehly without Silvio Berlusconi.
Here’s a very short resume of the man, to put things in the right context: Born and raised in a middle-class family, Silvio Berlusconi made his fortune in the real estate industry between the mid-1960s and the late 1970s, building some visionary housing complexes that are still regarded as some prime examples of “ideal city” featuring green spaces and all services integrated in the neighborhood.
While doing so, he did not neglect his childhood passion, football. His first company Edilnord also featured a football club, of which he was, of course, the President, but also the coach. That was the track record that, years later, would make him feel entitled to “offer” his coaching tips (and expect them to be implemented…) to most of the managers on his payroll, be them Carlo Ancelotti or Clarence Seedorf.
“I know who the right manager for Milan would be,” he joked (but maybe not…) in 2014, at the dusk of his age as the Rossoneri owner, with the club now struggling both in Serie A and internationally: “Silvio Berlusconi.”
When he put his hands on Milan, in February 1986, Berlusconi had switched from the real estate to the TV industry. He was now the owner of three private TV channels, the first media outlets aside from the state-owned RAI channels to broadcast across all Italy.
Since the Italian law did not allow yet for private networks to be “live” at a national level, he used the escamotage of sending recorded tapes of his programs to multiple local TV stations and broadcasting them with a few minutes of delay from each other. Again, pure Italian shrewdness and art-of-making-do. But that experience was important because it put him in contact with the man who would become his right hand at Milan: Adriano Galliani, another entrepreneur who owned a small broadcasting services company but also happened to love calcio.
Berlusconi and Galliani took over a once-glorious club that was gasping for breath, left on the verge of bankruptcy by the previous owner Giussy Farina, and coming from two seasons in Serie B in the past four years. It was difficult to do worse than that. Still, Berlusconi’s impact on Milan was immediate and revolutionary: The club, we said, is a corporate company, where everybody has a role. The footballers’ role is to play and that must be their only concern. The club will take care of everything else, be it making sure their bills get paid or their kids have the right school to go to.
The first season of the Berlusconi age was encouraging. Managed by Nils Liedholm, a former Rossoneri legend as a player, the team snatched a UEFA Cup qualification after a playoff with Sampdoria. The season wasn’t all roses, though. In a Coppa Italia game, Milan were outclassed by Serie B side Parma and their unknown young coach, who seemed to preach an audacious football credo. Berlusconi, who didn’t like to lose, enquired: “Who is this guy?”
That guy was Arrigo Sacchi and, a few months later, he was sitting on Milan’s bench.
That was the first of his visionary ideas applied to football, putting in charge a gaffer with basically no pedigree while building a team with huge ambitions. Because if the choice for a new coach was a bet, Berlusconi and Galliani’s first transfer market acquisitions were straight to the point: First the young talent Roberto Donadoni – whom they reportedly snatched from Juventus – then the fantastic Dutch trio, Ruud Gullit, Marco Van Basten, Frank Rijkaard.
In the space of two seasons, the Rossoneri became the state of the art of football. Sacchi’s fast-paced, offensive-minded calcio philosophy and his battery of champions took the Serie A by storm. Milan won the title in 1987/88 after a thrilling battle with Diego Maradona’s Napoli, recovering a five-point gap from the Partenopei and beating them 3-2 at the San Paolo in an epic title decider.
The following year, Milan had their European consecration, clinching the European Cup (the Champions League’s forefather) for the first time in 20 years. During their 1988/89 European run, Arrigo Sacchi’s Milan probably showed their best football, forever immortalized in the last two games they played – first, a 5-0 demolition of Real Madrid in a Semi Final second leg, and then wiping out Steaua Bucuresti of Romania 4-0 in the Final.
Between the end of the 1980s and the beginning of the 1990s, Silvio Berlusconi’s Rossoneri cemented themselves as a truly international Team with a global resonance and appeal. While domestically they had to surrender their title hopes to Giovanni Trapattoni’s “Inter dei Record” and then to Napoli, outside of Italy Milan were no match for any opposition. They won again the European Cup in 1989/90, adding two European Supercups and two Intercontinental Cups (brushing aside Nacional Medellin of Colombia and Olimpia Asuncion of Paraguay in what once was the epic, one-off game between the European and South American club champions) to their trophy cabinet.
Silvio Berlusconi was the man to be. While his media empire thrived and his Milan side reaped successes across the world, he would occasionally pay a visit to his boys during training sessions, landing on the pitch with a helicopter like he had done in the day of his introduction, and casually throwing his overcoat at some obsequious assistant who had to promptly grab it. Like a boss.
If that wasn’t clear, Berlusconi had quite a high opinion of himself and his beloved creation. A story frequently recollected by Italian journalists narrates about that day when he met with Pope John Paul II. Apparently, he was not told that he was supposed to deliver a speech to the Holy Father, so he had to improvise: “You know, Your Holiness,” Berlusconi commenced. “You are very similar to my Milan. You are frequently away, like us, to bring around the world a winning idea, which is the idea of God.”
On top of informing the Pope that he was created at Milan’s image and likeness, Berlusconi often remarked that “Italy is known around the world for three things: mafia, pizza, and Milan.”
But even the Invincibles have their down periods and, when in the summer of 1991 Sacchi left Milanello to become Italy’s coach, Berlusconi’s perfect machine was tested for the first time. His solution to fill the gap was as visionary as usual, as the newly appointed manager was Fabio Capello – whose only previous experience in the dugout was as a Rossoneri caretaker for a few weeks in 1987.
But, once again, the intuition was a right one. Fabio Capello’s Milan turned out to be, if possible, even more dominating than Sacchi’s. Milan won three Italian titles in a row, and four in five years. In 1991/92, they won the Scudetto without losing a single league game. In 1993/94, they clinched the title by never scoring more than two goals per game and conceding only 15 (!) in 34 matches.
During the same season, the Devils added another pearl to their European collection in what went down in history as Fabio Capello’s Milan’s signature game: It was a 4-0 thumping of Barcelona in a Champions League Final played in Oslo, with the Blaugrana coach Johann Cruijff left dumbstruck after having incautiously boasted about his chances of winning the cup in a pre-game presser.
On the other hand, Berlusconi and his faithful Galliani continued to run riot in the transfer market arena. They wanted that player, they got him, especially if – in one way or another – the player in subject had happened to cross and disrupt Milan’s path.
Crvena Zvezda of Beograd won the European Cup in 1990/91, succeeding to Milan? Berlusconi would bring to Milanello the “Genius” Dejan Savicevic, their brightest star and, for his own admission, his favorite player ever.
Olympique Marseille kicked the Rossoneri out of the competition in the same season? If you can’t beat them, buy them. And so, two seasons later, France talent Jean Pierre Papin donned a red-and-black jersey.
That said, there is a “before” and an “after” in the Age of Silvio Berlusconi at Milan. Right in the days when Milan dismantled Barcelona in the Champions League Final, Italy was going through an epochal change in its political landscape. With the umpteenth coup de theatre in his career, Berlusconi had announced he would run for Prime Minister leading his brand-new party named Forza Italia and a newly formed center-right coalition.
Since the days of his life-changing discesa in campo, things would never be the same for the club. Without getting into the details of his controversial, see-sawing political trajectory, suffice to say that Silvio Berlusconi’s commitment to Milan inevitably started to fade as he got involved in the country’s matters.
When Capello also left the Rossoneri in 1996, a few lackluster seasons followed, which many attributed to their owner’s progressive disengagement. The fan base started to grumble. “Enough with Forza Italia, from now on only Forza Milan,” a banner at the San Siro once warned him.
But Berlusconi was still there and made his presence felt. In 1998/99, Milan caught an unexpected Scudetto with Alberto Zaccheroni at the helm, coming from behind to pass Lazio at the last lap. In the following season, another calciomercato hit joined Berlusconi’s court at Milanello as he secured the services of the “Nightingale of Kyiv” – Dynamo’s starlet Andriy Shevchenko.
In the meantime, he didn’t refrain from offering his (unsolicited) tactical advice. When Italy suffered a heart-breaking defeat to France in the Euro 2000 Final, his assessment of the Azzurri coach Dino Zoff was caustic: “Our coach was unworthy, he acted like a true amateur. You just cannot leave Zidane free.” Zoff was so offended that he resigned immediately after.
In 2001, Berlusconi caught a major political success. He won the Italian elections, conquered a wide majority in both the Parliament chambers, and became Prime Minister for the second time, after a short stint between 1994 and 1995. As his political power peaked, he became much more than “the President of Milan” and turned into the most polarizing character in Italy, the subject of ferocious hate and undeclared admiration.
Political leaders and commentators alike frowned at his bizarre antics and his often-untimely exploits on the world scene. From defining US President Barack Obama “tanned”, to making German Chancellor Merkel wait several minutes to officially greet him ahead of a NATO Summit because, he said, “I was on a phone call with the Turkish PM Erdogan.” During a G20 Summit, Queen Elizabeth II scolded him like a child because he was shouting too loud as the world leaders posed for a group picture.
However, Milan continued to thrive. The third major winning cycle in the Berlusconi presidency opened when Carlo Ancelotti became the manager of the Rossoneri. That same Carlo Ancelotti who was a Milan player during the Sacchi days.
After a four-year desert crossing across the turn of the century, more trophies came. The Champions League won in 2002/03, beating Juventus on penalties in the first all-Italian Final in the top European competition. The 2003/04 Scudetto, which coincided with the breakthrough of the Brazilian talent Kaka.
Another Champions League in 2007, the last of the Berlusconi Age, with Milan taking revenge against Liverpool two years after the Reds had inflicted them the most shocking defeat ever – canceling a three-goal deficit in six minutes before prevailing on penalties.
Political commitments kept Berlusconi away from Milanello and the club for long stretches of time but, make no mistake, no one at Milan should forget who the boss was. In April 2004, Milan won a Derby di Milano in emphatic fashion, coming from behind after being down 0-2 to Inter at half time. Berlusconi was happy but irritated at the same time. So, he announced to the press: “Tomorrow I will send a letter to the Milan coach. I will explain to him that Milan – just because they ARE Milan – must always play with two strikers.” So long to Ancelotti’s beloved “Christmas Tree” 4-3-2-1 module.
But football was changing. Ancelotti’s departure in 2008 coincided with the beginning of an inevitable decline. Berlusconi no longer had the time and the finances to compete in a football landscape that was shifting dramatically. His final calciomercato hits consisted in big names who were quite past their prime, be it Ronaldinho or David Beckham.
Zlatan Ibrahimovic was perhaps the last major transfer market success, and his arrival coincided with the last Scudetto won by Silvio Berlusconi’s Milan. It came in 2010/11 with Massimiliano Allegri at the helm, and that was perhaps one last bet won by the visionary owner, who offered Allegri his first major role in the dugout after a couple of promising seasons at Cagliari.
When Ibrahimovic was sold, together with defensive stalwart Thiago Silva, at the end of the following season, it became clear that the glory days were over. The club needed to monetize. As Andrea Agnelli’s Juventus started to put their grip on the Serie A, the Rossoneri progressively fell behind in the league’s pecking order. Poor Galliani had to make do on the calciomercato with his now scarce resources.
The last few seasons were an ordeal as Milan also disappeared from the European landscape, their traditionally favorite hunting ground. In 2016, just a few months before a tormented negotiation would transition the club from his hands to those of the mysterious Chinese entrepreneur Yonghong Li, Berlusconi took stocks of the bad performances of the Rossoneri – in his own way, of course.
During a gala dinner, he theatrically patronized his players, who listened silently: “We cannot keep making such poor figures! I have been talking to these gentlemen [some sponsor representatives], who give us a lot of money. They just told me that, if we keep playing like that, they won’t give us any more money. Then, I will ask such money to you. No, better: I’ll stop paying you, so you will have to sue me. Do you know how long does a trial last in Italy? Eight years!”, he said, showing once again his perfect understanding of who things work in the Belpaese.
One could say that Berlusconi knew a great deal about trials because he was involved in so many, being at various times accused of tax evasion, false accounting, bribery, defamation and so on and so forth. Ultimately, he was only convicted for tax evasion – but that is such a controversial and complicated matter that falls outside of our purpose here.
The end of the story is known: On April 13, 2017, the Age of Silvio Berlusconi at Milan came to an end with Mr. Li’s purchase of the club. A few months earlier, Milan had won their last trophy, an unexpected Supercoppa Italiana success over Juventus on penalties. Berlusconi left after 31 years at the helm, and after having collected 29 trophies. No other football club owner, domestically or abroad, has ever won that much. Many years before, and with many accomplishments already behind him, he had pleasedly remarked: “I taught Milan how to play football.” Period.
However, if that was the end of the Milan story, the old entrepreneur still had the energy for a new challenge, together with a Friend. In April 2018, during a dinner, Galliani came close and whispered to him: “The Colombo Family has put Monza on sale.” Galliani was born and raised in Monza, and the Biancorossi were his childhood club. Berlusconi smiled: “Adriano, just go and do it.”
Four years later, a club that had never seen the Serie A during their 106 years of existence, achieved promotion to the top-flight.