Former Italian prime minister Silvio Berlusconi died Monday at the age of 86.

Berlusconi, who ultimately became a billionaire, wasn’t born into luxury. He grew up in Milan in a middle-class family, the son of a bank employee and housewife. He went on to study law at the University of Milan but made his mark in business before moving on to politics.

Politics

Berlusconi was elected Italy’s prime minister four times—in 1994-95, 2001-05, 2005-06, and 2008-11—for nine years total. His tenure made him the longest-serving post-war prime minister in Italy. His party was the center-right party, Forza Italia, which he led for over a decade—he also helmed the revived version in 2013. The party’s name was a soccer cheer, literally translating to, “Let’s go, Italy!”

Soccer

That was no coincidence—Berlusconi was a massive fan of the beautiful game. His dad, he recalled, used to take him to watch AC Milan, one of Italy’s historic football teams. But historic doesn’t always translate into victories. By 1980, AC Milan had been relegated to Serie B, Italy’s second tier—a serious demotion that resulted in less money and more financial challenges.

Berlusconi bought the team in 1986, saving it from near bankruptcy. He constantly promoted the team—and in his first season, he and the team made a dramatic entrance into Arena Civica, arriving in helicopters to Wagner’s “Ride of the Valkyries.”

He wasn’t all flash. Under his ownership, AC Milan won 29 trophies in 31 years, including eight Serie A titles and five European Cups. After three decades, he agreed to sell his stake in the club to a group of Chinese investors for 740 million euros (then $788m).

Scandals

As Berlusconi’s wealth grew, so did the stories surrounding him.

In 2010, a then 17-year-old Moroccan belly dancer called Karima Keyek, better known by her stage name Ruby Rubacuori, or Stealer of Hearts, raised eyebrows when she said Berlusconi had given her cash and jewelry. She also shared details about private parties held in his mansion—the so-called “bunga-bunga” parties he threw at his villa. Berlusconi’s second wife divorced him over the scandal, and he faced criminal charges related to paying a minor for sex—he was initially found guilty, but the verdict was overturned on appeal.

Tax Fraud

Accusations and scandals followed Berlusconi for years, and nothing seemed to stick—until he was convicted of tax fraud.

The tax fraud scheme involved a series of offshore companies. Berlusconi was charged with using the companies to buy TV rights for nearly 3,000 films and, based on the value of those films, claiming certain tax breaks. The rights were later resold to related companies at inflated prices, and Berlusconi was accused of pocketing the difference. According to prosecutors, it was a deliberate and significant case of tax evasion.

Berlusconi was initially sentenced to a four-year prison sentence, a sentence Berlusconi referred to as “a political, incredible and intolerable judgement.” He went on to say, “It is without any doubt a political verdict just as all the cases invented against me are political.”

His jail sentence was eventually reduced to one year because of prison overcrowding. And even after the conviction was upheld in 2013 following an appeal, Berlusconi managed to avoid jail time. His sentence was eventually commuted to community service due to his age.

He was also punished with a hefty fine of 10 million euros and a multi-year ban from holding public office.

Berlusconi’s ban from public office was set to expire in 2019, but following an appeal from his lawyers, a court in Milan overturned the ban, finding that he had been rehabilitated.

More Politics, More Soccer, More Scandal

In January 2019, at age 82, Berlusconi expressed his intention to throw his hat back into the ring. He announced that he would return to politics “out of a sense of responsibility” to stand for the European parliament. He became the oldest member of the assembly, but his roll-call attendance clocked in below 59%—missing almost 1,700 votes, more than any other member.

Berlusconi also got back into the game—football. His holding company, Finnvest, took over AC Monza in 2018. The team finished fifth in Serie C, Italy’s third tier, in that first season. By the start of the 2022 season, the team was back in Serie A, Italy’s top league.

Still, scandal followed. At the team’s Christmas party, Berlusconi promised, “I’ll bring in a busload of whores“ if they won an upcoming game against Inter, Juventus, or Milan—their competition. Monza went on to sweep Juventus in regular league play.

Finances And Legacy

Around the time of his death, Berlusconi and his family were estimated to have a net worth of $6.8 billion, landing him at #353 on Forbes’ billionaires list.

His wealth may be easy to quantify, but his legacy is ultimately complicated. Perhaps no one expressed this more than Former Italian Premier Matteo Renzi who noted on Twitter that Berlusconi could be divisive: “Silvio Berlusconi made history in this country. Many loved him, many hated him: everyone today must recognize that his impact on political but also economic, sporting and television life was unprecedented.”

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