The life and times of Silvio Berlusconi: How Italy's controversial Prime Minister became one of European football's greatest-ever presidents

"He is good, smart, kind, and able to stimulate our lads," the club president said. "But I decided to add extra stimulation, so I told the lads, 'You will play Milan, Juventus, etc... so if you beat one of these big teams, I will have you greeted in the locker room by a bus full of whores!'"

It was classic Berlusconi and his 'joke' was met by laughter in the room. However, when a video of the speech went viral, many Italians - who had long considered Berlusconi a national embarrassment - failed to see the funny side.

Which was wholly unsurprising, of course. The media mogul remained a hugely divisive figure across the country. His political career was blighted by scandal and yet, in 2022, he managed to secure a senate, while his Forza Italia party became a key component in the new right-wing coalition government led by Giorgia Meloni.

What is beyond dispute, though, is that Berlusconi made history in football, time and time again, first with AC Milan and then at Monza.

Funnily enough, Berlusconi always felt his work went unappreciated, particularly at San Siro. Back in 2004, he complained, "They speak of the Milan of [Arrigo] Sacchi, [Alberto] Zaccheroni and [Carlo] Ancelotti and never talk of the Milan of Berlusconi. Yet it is I who for 18 years has been picking the team, stating the rules and buying the players... It seems as if I do not exist!"

In truth, though, both Berlusconi and his contribution to Italian football were impossible to ignore. It was he who awakened Serie A's sleeping giant. The club was on the verge of collapse when Berlusconi took over in 1986, and he deserved immense credit for doing so, because Milan was not a particularly attractive proposition at the time.

"Milan's [financial] situation would have discouraged anyone," he pointed out shortly after the acquisition. "Even now the gaps in the accounts have not been found and the amount of debt is not fully quantified, but it was impossible to behave differently.

"On the one hand, there was a Milan that could be exposed to dramatic situations - bankruptcy, liquidation, courts etc. On the other, though, there was Berlusconi the fan, who did not feel like witnessing such a massacre. At that point, the heart intervened and the decision to buy Milan was obligatory."

It was a gamble that paid off spectacularly, thanks to both Berlusconi and his right-hand man, Adriano Galliani. In just three years, the pair put together arguably the best team club football has ever seen.

"According to [a FIFA vote], Arrigo Sacchi's Milan played the most beautiful football in history. It's actually difficult to say, but certainly the thrill of seeing that team play was incomparable," Berlusconi later told the Gazzetta dello Sport. "I'm happy that my father, who had led me by the hand since I was a child to rejoice and suffer for Milan, was still alive to see it."

Sacchi's side were certainly a joy to behold, one of the few teams in history that actually changed the game, thanks to their brilliant Italian backline and trio of Dutch superstars: Marco van Basten, Frank Rijkaard and Ruud Gullit.

The appointment of Sacchi had been key, though, another high-risk move that proved a masterstroke. He had one title to his name - the Serie C1 title - and his arrival at San Siro was greeted with a mix of scepticism and incredulity. Many influential figures in the media were aghast that the responsibility of reviving Milan had been entrusted to a coach that had never played at the highest level.

Sacchi famously reacted to the questioning of his qualifications by quipping, "I never realised that in order to become a jockey, you have to have been a horse first."

Milan won eight trophies during Sacchi's spell in charge, including back-to-back European Cups, and all while playing a brand of football that changed the game. It was, as Berlusconi put it, the most beautiful beginning to an "epic" empire that saw him become the most decorated president in club football.

Hardly surprising, then, that he came to consider himself an expert in tactics. Throughout his three-decade tenure, there were reports and accusations of interfering in team selections. At one point, he even publicly declared that "any Milan coach will be obliged to play at least two strikers. It's not a request; it's an obligation."

In that context, it's a minor miracle that Ancelotti managed to last eight seasons at San Siro. He didn't just have to put up with his president not only questioning his formation and selections, there were also little digs at his portly frame!

By the end of Ancelotti's time at Milan, though, it was starting to become clear that Berlusconi was no longer in a position to continue pumping money into the club. In 2009, he even addressed talk of a potential sale but, in typically self-aggrandising fashion, Berlusconi claimed that he had yet to find a buyer "who would benefit the club more than me".

What followed was a gradual but noticeable reduction in spending. Milan won the league in 2010-11 but lost key duo Zlatan Ibrahimovic and Thiago Silva to Paris Saint-Germain the following year - the clearest evidence yet that Berlusconi could no longer keep up with the sport's nouveau riche. Indeed, when he finally parted company with the club in 2017, he lamented that "to compete at the highest level in modern football requires investments and resources that a single family is no longer able to sustain."

And that appeared to be that, as far as Berlusconi was concerned from a footballing perspective. He was 80 years old and still very active in Italian politics. However, just over one year later, Berlusconi was back, having been surprisingly convinced to buy AC Monza by his old friend and most trusted advisor, Galliani.

The Biancorossi's potential was undeniable. Located in one of the most industrious areas in northern Italy, in a city home to one of Formula 1's most famous race tracks, not far from the metropolis that is Milan, Monza had attracted plenty of ambitious investors in the past. However, where others failed, Berlusconi succeeded, spectacularly, taking Monza from Serie C to Serie A in just four seasons - an achievement made even more incredibly by the fact that they had never previously played in Italy's top-flight.

“It’s amazing for a club like Monza, founded in 1912, to gain promotion after 110 years," Berlusconi said after the play-off final win over Pisa in 2022. "Being in Serie A, we must win the Scudetto and go to the Champions League and win it too. I am accustomed to winning all the time, so let's see..."

Monza may not have achieved the lofty goals Berlusconi had in mind - but he lived long enough to see the club beat Juventus home and away during a debut season that saw them finish 11th in the Serie A standings, while he was also understandably proud of the foundations he had put in place to help the Biancorossi achieve future success.

"We doubled our training ground, Monzello, which is now the biggest and most beautiful in Italy," Berlusconi stated. "We have also put in place the stadium with a small expenditure of €25 million (£22m/$27m). So, things have changed: when we arrived, there were 300 people watching Monza, now there's 10,000."

Berlusconi's passing, thus, came as a bitter blow to Monza, who were relegated in 2025 - just two years after the death of their controversial but charismatic benefactor, whose legendary status played nearly as big a role as his wealth in attracting players to the club.

As success stories go, Monza's brief rise to prominence might not have been quite on the same level as taking Milan from the verge of bankruptcy to world domination, but it was another undeniably impressive achievement by Berlusconi in the incredibly competitive world of football.

Unsurprisingly, his death divided opinion in Italy, primarily over whether he did more harm than good during his personal and professional life. He certainly wasn't mourned by many women or leftists. And if he did make it to heaven, he might well have had a few angry angels to deal with upon his arrival. But, for whatever it's worth, he was one hell of a president for Milan and Monza.