In 1992, Gianluigi Lentini was signed by AC Milan for a world record transfer fee of £13m. The press carped on about it in scandalised terms: murmurs about Vatican outrage here, griping about moral decadence there. A world away from Milan, in a tidy but dull Dublin suburb, hearing mention not of millions but billions of lire in relation to the transfer was a shock to the system for a young Irishman to whom £1 meant a week’s worth of Maxi Twists. More so since the club had splashed out on the sly, lethal Papin that very same summer. Didn’t they realise they already had Van Basten, Gullit, Donadoni? Why did they need any more? A short, greasy man the papers kept calling a “mogul” appeared to be losing his mind, spending most of his cash on football players. It all seemed so impossibly glamorous.

From the moment the news of Lentini’s signing broke, an obsession with all things AC Milan and Serie A took root in the mind of that once-innocent Irish lad. It turned out to be a fascination that inexplicably failed to dwindle in the face of relentless corruption, falling standards and apathetic crowds, not to mention the rise of less alluring competitions – such as the admirable but overly wholesome Bundesliga. Though both the club and the league may have lost the lustre of their 1990s peak, they retain the glorious pomp that separates Italian football from the rest through the projection of a uniquely Italian bravura: a bizarre magnetism derived from the country’s chaos, drama and style. “If there’s one club that sums up everything good, bad and ugly about Italian football, it’s AC Milan,” was the perfect summation of The Rough Guide to Cult Football. “Their history covers glory and shame, brilliance and bluster, technical genius and boardroom chicanery.”

Even in decline, it’s a combination that’s hard to resist.

It’s now very clear that AC Milan are in trouble. After years of going nowhere fast they are suddenly going backwards. The playing squad is populated by overpaid, average footballers, while those in the boardroom are preoccupied with the typically petty, self-absorbed squabbling so common to Italian club direction, but which the omnipotence of Silvio Berlusconi had kept in check for so long. Now, Don Silvio’s influence is waning and there’s a new Berlusconi on the block: his daughter, Barbara.

Barbara’s main adversary is Adriano Galliani. She wants him gone and, sooner or later, she’s likely to get her way. But Galliani is a hard man to shake off and, for now at least, he remains in place after “crisis talks” in May. In many ways, Galliani is as ‘Berlusconi’ as Barbara herself, having been there from the very beginning of Silvio’s Milan regime in 1986. His relationship with Berlusconi is comparable to that of Passepartout’s to Phileas Fogg: a wonderfully resourceful factotum. Galliani’s departure would be as much the end of an era at Milan as Berlusconi selling the club, rumours of which have been circulating over the past year or so. Singaporean businessman Peter Lim is mooted to have made a bid.

If any bid for control of Milan were successful, it would signal a marginalisation of Silvio Berlusconi within the club, a retreat that would occur in tandem with his gradual disappearance from the forefront of public life in Italy.

Love him or hate him, Berlusconi helped change football in Italy – and beyond – when he took control of Milan in the mid-1980s. He brought the club from the brink of anonymity to the peak of world football in half a decade, turning what had become an ordinary provincial team into a flash, attractive and gifted side that captivated a continent. You may not miss Silvio when he goes – he is after all a comically vulgar specimen – but we shouldn’t lose sight of the fact that what he set into motion at Milan had a profound effect on the game, as well as Italy itself.

“When dealing with modern Italy,” writes Paddy Agnew in Forza Italia, “it is impossible to ignore Silvio Berlusconi. […] This applies as much to football as to politics or business.”

Berlusconi is nothing if not an opportunist. So much of his success in all walks of life has come about by seeing a chance and taking it. He started out in construction, building luxury compounds, but spotted a niche when cable TV began to be deregulated in Italy. The residents of his élite gated communities wanted more from their televisions, and Berlusconi was only too happy to provide it. Gradually, the majority of transmitters in Lombardy were snapped up by Mediaset, Berlusconi’s media company, and in the early 1980s, it became clear that televised football could drive huge viewing figures in Italy. Mediaset’s flagship channel, Canale 5, carved out a name for itself based on its coverage of the sport, and by the middle of the same decade, Berlusconi had become a media baron. Over the years, Berlusconi changed the way people watched football. Out went the old-fashioned, and in came the dancing girls, comedians and everyday celebrities to spice up the world of football coverage. Footballers became the object of TV gossip, a notion seized upon by Berlusconi’s channels.

“The modern history of Milan can now be written only with reference to a key moment: 20 February 1986,” says John Foot in Calcio. In the months preceding that moment, Don Silvio had begun to take an interest in AC Milan. Then as now, the club had stagnated, floundering in mid-table in the aftermath of a relegation and – shock – a financial scandal, so Berlusconi got the club on the cheap. Quickly, he set about revamping Milan in his own image: grandiose, loud and ambitious. Berlusconi wanted the club to be successful, for it to reflect on the pitch his own achievements off it. But the club was more than a vanity project; it was a commercial crutch, an enhancement of the Berlusconi brand. To make it work, he needed the team to win, so he began spending money.

Long before the famous purchase of Lentini, in came the Dutch trio of Gullit, Van Basten and Rijkaard. Van Basten had been courted by Berlusconi at the Italian’s palatial villa in Arcore, while it had taken two flights in a private jet to convince Gullit to come to Milan. By the time Rijkaard arrived in 1988, the club was soaring, with home-grown players like Paolo Maldini, Billy Costacurta and Franco Baresi emerging to complement the international stars. At the end of Rijkaard’s first season, Milan had returned to the top of Serie A, their first title since 1979. Berlusconi’s shrewd direction, ably assisted by Galliani in the role of roving talent-scout and head coach Arrigo Sacchi, had paid instant dividends. The appointment of Sacchi was famously a masterstroke, with the little man from Fusignano electrifying the then staid world of Serie A with a unique brand of high-pressing, technical attacking play. Alongside the Dutch triumvirate, Sacchi was integral to Milan’s early success, and it was the vision of Berlusconi that brought them all together.

Relentlessly, his media empire rammed AC Milan down the throats of TV viewers, forcing their popularity on the audience – of course, it helped that they were in fact an outstanding side – and bringing in huge amounts of revenue to bolster the team. Already, Silvio was indicating a strong desire to take a hands-on approach to his new acquisition. Over time, it would be an approach that would help sweep him into power as the Prime Minister of his country.

While Milan were busy conquering Europe, retaining the European Cup in 1990 after doling out a thrashing to Steaua Bucharest in the 1989 final, a political system that had dominated half the continent since World War Two was receding. Communism’s collapse in eastern and central Europe worked along roughly the same timeline as AC Milan’s return to prominence. Italy, with its borders on Yugoslavia, had long centred its politics on the “red threat”, with the prime focus of political parties there being to keep left-wing politics out of government. So when communism disappeared as the fear factor, Italian politicians were at a loss. Sensing his time had come, the arch-opportunist Berlusconi seized centre-stage and launched his political party, Forza Italia, in 1993. In May 1994, AC Milan scorched Johan Cruyff’s Barcelona in the Champions League final: one month later, Silvio Berlusconi was Prime Minister of Italy. It was all about symbiosis: football, politics and media – the triple-pronged attack that put Silvio Berlusconi and AC Milan at the forefront of a continent’s attention.

On the pitch, Milan won in style. It was not for nothing that Berlusconi had, memorably, registered the club to his company’s “entertainment” wing. He wanted the team’s football to win hearts and minds, and his eccentric little coach helped deliver on that. Sacchi’s attacking strategy, as well as the presence of a number of charismatic players, made them a mouth-watering prospect. At the back they were iconic, intimidating and classy: there was Baresi, the great libero described so evocatively by Sheridan Bird as a “rumpled leader”; Maldini, pre-Raphaelite god and gifted reader of the game; Costacurta, sheer class; Tassotti, hard as nails. The midfield was anchored by Rijkaard, Ancelotti and Albertini, flanked by a variety of stars like Donadoni, Boban and, of course, Lentini. Up front there was Van Basten, the “Swan of Utrecht”, Gullit, and a host of others such as Simone, Massaro and Papin. Early-Berlusconi Milan was a super-team.

They, along with a general uplift in the fortunes of Italian football, made Serie A the most attractive league in the world by the mid-1990s, with Sampdoria, Juventus, Inter and Parma all either winning or reaching the final of Europe’s two main continental competitions. Now, to hear the names of even mediocre players of the epoch is to experience instant retro-zeitgeist, to be transported back to a time when the “A” pitches were stalked by the best in the world, and the league dominated the international transfer market. From 1952 to 2000 the world transfer record was broken 22 times, 18 of which were by Italian clubs. In the 1990s, with the league awash with cash, Serie A broke the record six times. The Milan method had spread fast.

With Berlusconi’s channels now piping the league – and his populist political message – into millions of homes, the decade became a golden era for Serie A. Indeed, television coverage is central to the perception of the league. Even from the point of view of an outsider looking in, one can’t look back at the glory years of Serie A without seeing them through the prism of how they were transmitted to our own lonely north-western isles. Enchanted by the dulcetry of James Richardson and Peter Brackley, a certain generation of Channel 4 viewers in the UK and Ireland will always associate the league with Gazzetta Football Italia.

Fittingly, though, it was television that was to end the boom-time that it created in Serie A. “Many of these teams were built on borrowed money and had fanciful expectations about future incomes”, Richardson himself told The Guardian in 2006. “And when the TV bubble burst, the whole thing collapsed.” Milan hung on longer than most, largely because of the acumen of their padrone. While the league was collapsing around them, the club was reborn in the mid-2000s after a quiet period in the late ‘90s and the early-millennium. Berlusconi had lost his mandate in the Italian cabinet in 1995, and did not return to office until 2001, where he would remain on-and-off until 2011. Not long after his second term had begun, his government passed “creative accountancy” legislation that allowed Milan to write off losses of almost €250m. Coincidentally – or not – this return to power overlapped with two Champions League victories in ’03 and ’07, while the 2005 final proved to be simultaneously one of the great European stories and one of its greatest injustices. Milan were as powerful a club as any in the world during this period, particularly given that Adriano Galliani was also serving as president of the Italian league at the time.

But it wouldn’t last.

The cracks had long since begun to appear in the Forza Italia setup. As the party’s fortunes dipped and lapsed into infighting, so too did AC Milan. The club wasn’t helped by a general drop-off in Serie A’s standards against the background of scandals involving match-fixing, bribery and general corruption. Berlusconi the politician was weakened, as was Berlusconi the president. Where once the club had been pulling off transfer coups like the capture of the three Dutchmen, they were no longer doing so, instead beginning to pay large wages for players not quite out of the top drawer – Sulley Muntari, Kevin-Prince Boateng, Keisuke Honda – and putting them in a team with veterans, journeymen and also-rans like Abbiati, Bonera and Taarabt. Worryingly for il Diavolo, their league record has seen the team win just two league titles in the 21st century, and from the second decade of the new millennium, AC Milan have begun to look a very average side indeed. Since their 2007 triumph, the club have not made it past the Quarter Final of the Champions League, only once going beyond the second round in that time, and will take part in the Europa League next year.

It’s hard to say with certainty exactly what is behind the decline, but it is most certainly tied up with the gradual weakening of both Berlusconi’s political and entrepreneurial power, as well as the infernal, internal power struggle. Additionally, Milan have been faced with the rebirth of one of their closest rivals, Juventus. Where once Milan were the innovators, splashing out on training grounds, ultra-professional organisation and administration, the Old Lady has since caught up or even overtaken them in that regard. Juve now have their own stadium – a rarity in Italy – and a modern training complex at Vinovo to rival Milanello. The Turin team have won three league titles in a row, and look ominously superior on the field to the rest of “A”.

Worrying also for Milan is the fact that the league’s middle-ranking clubs, often also-rans in comparison to the country’s big clubs, have recently started to catch up. Teams such as Roma, Lazio, Napoli, Parma and Fiorentina have all been resurgent over the past number of years, emerging to challenge the traditionally dominant trio of Milan, Inter and Juve. Sides like these now possess players of gifts comparable to those on the books of the big three. Fans who enjoyed “A” at its 1990s peak will know that the strength of the “second tier” teams made the league what it was – many of the best memories of Serie A were created by gifted sides emerging from mid-table normality to challenge for titles. Think of the Sampdoria of Mancini and Lombardo, the Fiorentina of Batistuta and Rui Costa, and the unforgettable Parma of Buffon, Thuram, Cannavaro, Veron, Chiesa and Crespo. Although today’s Serie A cannot be compared to its peak in the 1990s, it is currently a more competitive league than it has been over the past ten or so years, with the playing quality being as evenly distributed as it was in the final decade of last century. The Italian World Cup squad for Brazil contained just nine players from the big three – not a single Inter player made the cut – with Parma and Torino providing three apiece, and one each from Genoa, Lazio, Roma, Fiorentina and Napoli.

Perhaps, Milan have in recent times relied too much on foreign players, but a new generation of local youth is emerging to take the club forward. It is with them that the future lies, whether that be in the form of Stephan El Shaarawy, Mattia De Sciglio, Ignazio Abate or Mario Balotelli. A solid core of Italians must be fostered if the club is to regain an identity slowly slipping away with the demise of Berlusconi and the old playing guard. Fittingly, the man entrusted to guide the club in the right direction is Filippo Inzaghi, formerly Milan’s youth team coach.

Inzaghi replaced Clarence Seedorf as head coach, another ex-player whose installation at the helm was highly politicised, wrapped up as it was in the contretemps between Barbara Berlusconi and other club directors. Super Pippo will bring intelligence and guile to the role, facets of his playing style that have been reflected in his coaching manner at youth level. Though inexperienced like Seedorf with regard to management, his time with the primavera will have provided a foundation upon which he can build his career. He will hope to avoid the precedent of Andrea Stramaccioni, the former Inter coach who was also elevated to a first team position having impressed in his club’s youth setup.

Evidently, Milan like to promote from within and for some time now, Paolo Maldini has been hovering on the fringes of the Milan directorship: many see him as a potential replacement for Galliani somewhere down the line. Certainly, his connections within the game would make him an ideal candidate, while the prospect of a Maldini-Inzaghi axis will have many slavering in delight. If anyone has the authority and charisma to drag the directors back in line and arrest the slide, one feels it may be Maldini, though his influence and popularity make him an intimidating prospect for directors more concerned about their own careers. Should Maldini end up the new Galliani, he will have to replicate some of the transfer wisdom shown all the way back in the 1980s, when the bald eagle of Monza first helped the Dutch to colonise Milan.

Italy is a country familiar with falls from grace. The Romans were doing it long before it was cool, but we still look back in awe at their feats, at the glory they once achieved. We know that even if they no longer boast an empire, they once ruled half the world. There is, unquestionably, a legacy. So it is that whatever happens to AC Milan and Serie A, it should be appreciated that they are great institutions of our game, whose continued decline ought to be viewed not with schadenfreude, but with dismay. The football world is a darker place without a strong Serie A, and the league a dull one bereft of a marauding Milan – or Inter, for that matter. Those who delight in their fall should remember the joys with which they have provided us in the past. After all, even Silvio has his merits.