Our legacy is often defined through the eyes of the person depicting it. What we leave behind or are remembered for will never be finite, partly because it is based on the unpredictability of emotion. A great deed here could have hurt someone else there. Our actions and – perhaps more importantly – the consequences of them will vary immensely from person to person.

This is simply a fact of life and football is not unique in this regard. Fans will find any and every excuse to tear down a rival player’s worth and their team’s accomplishments, naturally because they usually coincide with their own misery. They will boil it down to things such as the competition they faced or even the aesthetics of their performance. This phenomena is expected, but it’s an entirely different dilemma when the merit of their accomplishments is clouded by their lack of morality.

For 31 years, Silvio Berlusconi was the constant at AC Milan. The visage of his pearly white smile and transplanted slick backed hair was as synonymous with the club as the colours red and black. He arrived in his Agusta helicopter as the all-conquering hero; equipped with deep pockets and a reputation for building business empires.

He was a novice to the world of calcio but it was hardly of concern. He exuded a confidence and a Midas touch that knew no bounds. Twenty-nine trophies would make their way to the Mondo Milan Museum during his reign, but so too would a litany of sexual controversies, bunga-bunga parties, corruption, racial remarks, homophobia, tax evasion and mafia association.

From a supporter’s point of view, much of what Berlusconi did in his personal time had little bearing on his ability to effectively run his club. Memories of transgressions or verbal gaffes vanquished over 90 minutes as the wins piled up and the good times rolled.

The later stages of his tenure would invite more introspection, a result of a deteriorating club and long-simmering anger over perpetual mediocrity. Nevertheless, inside the legendary walls of the San Siro, the mention of the name Berlusconi is still sure to conjure up positive feelings. Once you stroll past those tickled with nostalgia, his name can elicit palpable embarrassment to downright hatred. It’s a bed he has made for himself and one in which his memory will have to sleep in.

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The son of a bank employee and a housewife in Milan, Silvio Berlusconi was born in September 1936. He studied law at university and would eventually graduate with honours, but his true love was always music. For a while he was an upright bass player in a nightclub band before trading it in for singing gigs aboard cruise ships. The joy and adrenaline rush he could excavate from his performances never translated into a steady income. So, in the 1960s, he turned his focus to construction and real-estate development, spearheading the wildly successful Milano Due project.

In amassing his first small fortune, Berlusconi would also discover his limitless power of deception. Setbacks or questionable business practices would be disguised with bombastic declarations (one of his favourite sayings was to “Always carry the sun in your pocket”), and made-up quotations that he would attribute to famous American tycoons to instil motivation.

His cheeky smile and patented Silvio charm was hypnotic in its ability to earn him credibility and opportunity in an array of fields. Berlusconi first entered the world of media in 1973, starting up a small cable television company, TeleMilano, to service units built on his properties. TeleMilano was the first private Italian television channel, and later evolved into Canale 5, the first national private TV station.

Even as a young entrepreneur, Berlusconi possessed an acute understanding of what the masses craved. His television stations would become a utopia of entertainment and women, importing American shows such as Dallas, Dynasty and Baywatch. At the time in Italy, private stations could broadcast only locally, not nationally. Operating a semi-legal business would bring pause to many, yet Berlusconi overcame these statutory obstacles rather easily.

Then prime minister and head of the Socialist Party, Bettino Craxi, would become a close friend. In 1984, when judges in Turin, Pescara and Rome decided to shut down Berlusconi’s channels, Craxi simply issued a decree that reclassified his nationwide network of “local” stations as legal. It would emerge some years later that Berlusconi’s Fininvest media group funnelled close to 21bn lire (around $17m) into Craxi’s secret offshore bank accounts.

Ultimately, the decision came as a huge relief to millions of Italians and, most of all, Berlusconi himself. Their unbridled thirst for this new wave of television had made him some 113bn Italian lire (€58.3m) in the process, opening the door to a myriad of other business ventures. The continual amassing of assets and friends in high places was merely a shield for Berlusconi against inquires or prosecution. Having already conquered the worlds of media and publication, his earnest eyes would next set their sight on Italy’s second-biggest religion – calcio.

The 1980s were a tumultuous and scandal-ridden time for football in Italy. Two Roman shopkeepers, Alvaro Trinca and Massimo Cruciani, were approached by the Guardia di Finanza and grilled for hours on what they knew about corruption within the sport. A thorough investigation would eventually reveal the nefarious scheme, centred around a betting syndicate paying players and officials to fix the outcome of matches. Totonero 1980 was born, and with it came a cascade of relegations and substantial fines to some of the countries biggest clubs.

Original Series | The Football Italia Years

Sitting atop the list would be AC Milan; the defending champions and one of Serie A’s most recognisable brands. Their punishment would be harsh, subsequently relegated to Serie B for the first time in their history and stigmatised as a “cheating club”.

Milan achieved promotion back to Serie A on their first attempt, winning the 1980/81 Serie B title, but were again relegated a year later. In 1983, Milan won the Serie B title for the second time in three seasons to return to Serie A, but their squad was hardly convincing. The chaotic atmosphere surrounding the club would only be amplified in the coming years, as mounting debts would sink them to the brink of bankruptcy. It was a crippling realisation for Milanisti everywhere, and their slow decline would see Juventus take over the throne as king of the peninsula.

However, if Juventini believed that Milan’s supporters would be content to see their club dismissed to the role of court jester, it quickly became clear how very wrong they were. In December 1985, a large swath of the Milan crowd unfurled a banner across the San Siro urging the mercurial Silvio Berlusconi to buy their club and rescue them. The declaration may have well been a neon sign from heaven for the business magnate. With a desperate fan base now by his side, Berlusconi sat patiently, keen for a new Serie A TV deal to kick in after the New Year.

On 24 March 1986, Berlusconi officially took over, named Milan’s 20th president and its brightest hope for change. At a press conference a few days after buying the club, he declared: “Milan is a team, but it’s also a product to sell; something to offer on the market.”

Berlusconi’s vision to transform the club went far beyond just winning games and stashing trophies. More than just something that could be enjoyed on game days alone, he wanted AC Milan to represent a lifestyle. With this in mind, he pushed forward with the opening of an apparel shop near the city’s world0famous Duomo and the publication of the Forza Milan magazine. Milan had become a modern and progressive club, operating with an entrepreneurial spirit at odds with the still largely family-run world of the Italian game.

These measures instantly made the team more profitable, and a record 60,000 season tickets would be sold. The most important task, however, still remained. He needed to build a team that would keep Milan’s attention, so he assembled one of the greatest sides the world has ever known.

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Berlusconi’s first season in charge would show signs of immediate progress. Milan would finish fifth in Serie A, riding on Pietro Paolo Virdis’ league-leading 17 goals, in addition to qualifying for the UEFA Cup thanks to a victory in their playoff encounter against Sampdoria.

Beyond a few tinkerings, the expectation was for Milan to enter the new campaign mostly intact, but their new president had other ideas. While Juventus were implementing their blueprint of catenaccio, Berlusconi favoured an attacking style of play that could captivate the masses. His quest for a new manager would eventually lead to Arrigo Sacchi, a former shoe salesman turned ascending manager of Serie B side Parma.

Sacchi’s appointment was immediately met with criticism from the Milan press. They argued that such an inadequate player could never go on to be a successful coach, let alone at such a prestigious club. Sacchi, however, had different ideas, firing back at them: “I never realised that in order to become a jockey you have to have been a horse first.”

Along with Vice-Chairman Adriano Galliani, Sacchi devised a blueprint of what he wanted his squad to look like, and Berlusconi obliged with his chequebook. Inheriting a squad that already included Franco Baresi, Roberto Donadoni and a promising Paolo Maldini, Milan would sign Ruud Gullit and Marco van Basten to anchor the attack, while the midfield would be cemented with Roma’s Carlo Ancelotti.

Sacchi favoured a full press, with each of his players relentlessly attacking the ball. An added emphasis on fluidity and space were staples of his 4-4-2 formation. His philosophy would yield immediate results: Milan would capture the Scudetto in 1988 for the first time in nine years.

Vindication had washed over Sacchi but he was hardly satisfied. Frank Rijkaard would arrive in the summer, forming a Dutch triumvirate that could rival the attacking talent of any squad on the planet. The Rossoneri would simply become unplayable, marching their way to back-to-back European Cup triumphs in 1989 and 1990. It was a throwback to the glory days of the Roman Empire when vast tracts of Europe were plundered by its armies and raided of its riches.

It was in the midst of this euphoric time that Berlusconi recognised the immense power of the European stage. Up until that point, the tournament followed a winner-takes-all knockout format right from the beginning of each season. Concerned that his team could lose early and miss out on potential revenues somewhere in the millions, Berlusconi approached UEFA with the idea of making the competition a season-long affair. All parties eventually came to an agreement, renaming the tournament the Champions League and setting a new barometer for all of Europe’s top clubs to be measured by.

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Despite the tremendous success of Sacchi’s reign, his time at Milan would eventually come to an end as he left to manage the national team. He was replaced by Fabio Capello, who would guide the Rossoneri to three consecutive Serie A titles between 1992 and 1994, a spell which included a 58-match unbeaten streak in the league – earning the team the label ‘the Invincibles’ – and a string of three consecutive Champions League final appearances from 1993.

Seemingly everything on the pitch appeared to be going Berlusconi’s way, but his power off it was becoming more precarious by the day. A group of prosecutors in Milan launched an investigation into corruption in Italian politics and the results were staggering. Nearly all political parties were involved in some form of bribery, but Berlusconi’s old friend Benito Craxi’s Socialist Party was its chief benefactor.

Fininvest was found to be among Craxi’s biggest donors, and indictments were handed down to a number of executives. In fear that he too could face real prison time, Berlusconi decided to enter the political arena by founding the Forza Italia party.

The disillusionment many Italians now held for established politicians opened the door for an outsider. Despite his connections to the very same corruption they supposedly loathed, Berlusconi’s promise of a ‘Rivoluzione Liberale’ intoxicated the masses. Seemingly overnight, a political movement comprised of men in designer suits from his media empire were now in charge of the country.

Infighting amongst factions in his administration would see Berlusconi’s tenure as prime minister end prematurely, but his involvement in politics was far from done. He would be named prime minister again in 2001 and 2008, seizing much of the attention he previously afforded to his football club.

For a while, Milan barely skipped a beat. Galliani and his team of scouts continued to identify talent with astonishing accuracy, and the money being supplied by Berlusconi was instrumental in retaining it. Carlo Ancelotti’s appointment would take Milan to the pinnacle of European football once more in 2002 and in 2007, but only one Scudetto would find their trophy cabinet during his eight years in charge.

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The summer of 2009 would prove to be a flashpoint in the Rossoneri’s future, as Ancelotti departed to Chelsea and the beloved Kaká to Real Madrid. Since then, a revolving door of managers including Leonardo, Max Allegri, Clarence Seedorf, Pippo Inzaghi, Siniša Mihajlović, Cristian Brocchi, Vincenzo Montella and now Gennaro Gattuso have taken turns in charge.

Berlusconi’s involvement in over 20 court cases during his political career, including being sentenced to four years imprisonment (he served no time because of his age), and a five-year ban from public office for tax evasion in 2013 took an enormous financial toll. A €560m lawsuit against his holding company, Fininvest, was equally as damaging.

Star players such as Andrea Pirlo, Zlatan Ibrahimović and Thiago Silva were shown the exit door, replaced by the likes of Alessandro Matri, Philippe Mexès and the infamous Cristian Zapata. The image of a half-full San Siro slowly became the norm, as banners in the Curva Sud implored for their club to be saved from the very man that did the saving in 1986.

The once innovative and enviable Milan had slowly become a relic in the face of the modern game, and Berlusconi was public enemy number one. In the words of lifelong Milan supporter and illustrator Federico Manasse, “Solely in terms of the football side of him, I probably view [Berlusconi] similarly to how many Arsenal fans will view Wenger after he conclusively leaves. Berlusconi did wonderful things for the club, and helped it resurrect from the Serie B abyss, but during his last six years or so he was just clinging on to his toy without any regard for the fact that everything was going down the drain.”

It became clear that the situation was unattainable for all parties involved. Despite a litany of delays in negotiations and failed last-minute investment opportunities, Berlusconi sold his beloved Milan to Chinese businessmen Yonghong Li and David Han Li. The €740m transfer of power officially concluded an era of dominance in Milan and European football history. “I leave Milan with pain and sorrow, but knowing that in modern football, to be at the top in Europe and in the world, you need constant investments and resources that one family on its own cannot afford to provide anymore,” Berlusconi’s parting statement read.

For almost four decades, Silvio Berlusconi’s fingerprints could be found all over Italy’s largest institutions. His banishment from the political arena and subsequent sale of his club have put him in a very unfamiliar position of vulnerability. The days of seemingly limitless power have been replaced with campaigning for a party he can’t physically represent.

Where Milan now go under the ownership he handpicked will almost certainly have a rippling effect on his legacy, but it won’t end there. Some will remember the European Cups and the incredible teams; others the damaging scandals and lives interoperably ruined. For better or worse, however, what cannot be disputed is the colossal shadow cast over the club by one of Italy’s most divisive figures in modern history.

By Justin Sherman @JShermOfficial