The Fall of the Mighty: AC Milan's descent to Inferno 

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The Rossoneri
The past does not haunt us. We haunt the past. We allow our minds to focus in that direction. We open memories and examine them. We re-experience emotions we felt during the painful events we experienced because we are recalling them in as much detail as we can. - Augusten Burroughs

So did they, too. When they took to the pitch at the Olympic Stadium in Athens on the night of 23rd May 2007, the lacerations Milan had suffered two years ago seemed to be laid fresh and bare in their minds.

Carlo Ancelotti's men knew they would be fighting two battles that night. While the world held their breaths and anticipated nothing short of a war on the pitch, inside their heads, the Rossoneri found themselves in a skirmish against the evocations of that fateful night in Istanbul.

“It was an incredible loss. Ahead of the 2007 final, my team-mates – who were there for 2005 – were frightened. They were worried about playing against Liverpool again, so it proved a very important win. Even I was quiet before the game, but that’s part of my personality. Many of the others felt a lot before the match, but I tried to treat it like a normal game – even though it was a final." - Massimo Oddo

Pertaining to the words of Herbert Kilpin, the English expatriate who was one of their founding fathers, Milan was a team of voracious devils wearing the red and black strips looking to trounce and scare the living daylights out of their adversaries.

But for this once, seven of those eleven men found themselves shackled and locking antlers with the Inferno that was the devil's abode. They found themselves immured with the very red and black strips they had embroidered their hearts with.

Dida, Alessandro Nesta, Paolo Maldini, Andrea Pirlo, Gennaro Gattuso, Clarence Seedorf and Ricardo Kaka were feeling the heat of the Istanbul nightmare as if it had come to pass just yesterday.

Little did they know that the gods would favour them this time.

90 minutes and two Filippo Inzaghi goals later, AC Milan were wheeling away in vehement jubilation, buoyantly soaking themselves in the glory of their seventh European title.

While the aforementioned seven titans lent a helping hand in lifting the famous silverware, the crevices in the star-spangled squad were crystal-clear than ever; the cracks that later formed the base of the lamentable downfall of one of the greatest clubs on the earth.


The angel who turned into a demon

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Silvio Berlusconi was both the angel and the demon at the San Siro

It's in the nature of men, isn't it? To ignore a seemingly dangerous thing, condition or circumstance that looks trivial? And when we get the total blast of how perilous our ignorance proves to be, there's hardly any time for us to make amends.

Now, whether Silvio Berlusconi saw that chink in his thumping great squad of demigods or remained nescient about it is a question only he can answer. However, being the prime minister of Italy and above all, one of the most successful businessmen in Mussolini's nation makes it rather hard to believe he would have been unaware of the snag that would later take the shape of a Gordian knot that destroyed his footballing empire.

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Frank Rijkaard(L), Marco van Basten(M) and Rudd Gullit(R)

There's a part of Berlusconi's reign, a fable the Milan fans just love reminiscing; A 29-trophy haul that included five Champions League trophies, eight league titles, five Uefa Super Cups and one Club World Cup. In a manner of speaking, Berlusconi was very much the Messiah, the angel who rescued the Rossoneri from its darkest days and led them into a revolution.

His inquisitions of the three Dutch musketeers in Marco Van Basten, Rudd Gullit and Frank Rijkaard and then Arrigo Sacchi, one of the greatest tactical minds in the game's glittering history, kickstarted their era of glory.

Immortal as those names were, Berlusconi failed to know that the bodies were still...earthly and human; that one day they would wear out and the club would need adequate and able successors to safeguard the legacy of San Siro.

However, it's the last great team he built that we need to pay attention to; the troupe of players that won the seventh and the last Champions League title to date.

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Paolo Maldini was 39 when he captained AC Milan in the UCL 2007 Final against Liverpool

He failed to know, or should we say, ignore the fact that the legendary Paolo Maldini was 39 when he led his team to the final. He perhaps chose to turn a deaf year when his colleagues might have reminded him of the reality that Inzaghi (34), Seedorf (31) and Nesta (31) were steadily marching towards the act of calling time on their sparkling careers.

Only 3 players amongst the squad that conquered Europe were under 30, with every player apart from the artistic Kaka were 28 or above. It was a team of seasoned players protruding experience of the highest class.

Age was reflecting brightly, the very problem Silvio Berlusconi chose to ignore and reap the consequences later. And for not taking care when it mattered, from being the adored saviour that he was, the Italian owner was all of a sudden the demon that the Milan faithful wanted to banish from their beloved club.


The corollaries of financial conundrums

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AC Milan suffered financially due to multiple attempts to build a new stadium

If you ever walk down the memory lane to discern the causes that led to the fall of the giants, for sure, your eyes won't miss the financial conundrums that keep waving frantically at you. The paucity of monetary strength is a common factor in any of the tales about deceased football clubs, and the Rossoneri are no exception to the shortage of wealth.

To start with, Silvio Berlusconi had put the rival Italian clubs to shame with his extravagant spending. But, the Italian prime minister failed to cut off the debts that had haunted the club for almost a decade. But, that was just one of the many factors that strained Milan financially.

The Rossoneri's bank accounts suffered considerably due to their futile attempts to build a new stadium of their own and leave their tenancy at the San Siro behind. Furthermore, the global financial crisis of 2007 played its part in affecting the balance books.

It's unequivocal how the Serie A has not been up to snuff when pitted against other major leagues in Europe in terms of the popularity; the Italian league has seen its appeal plummeting in the recent years. Their adamance on sticking to their age-old defensive style of play and failing to adopt a more offensive and fast-paced method of football can be deemed responsible for the same.

As a result, with the league's revenues from TV rights going downhill; the clubs found themselves miles behind in financial competitions with their Spanish, English and German counterparts.

Last but not the least, the Italian billionaire's crusade in the country's political scene was an indirect curse to the club's wealthy coffers. The groundwork to the 2013 elections in Italy further exacerbated their already weak pecuniary stability with Berlusconi opting to steadily withdraw the financial input in the club.

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Silvio Berlusconi's political crusades affected the club's coffers severely

As Italy became a victim of financial turmoil, finance expert Andrea Bricchi, who covers economics for the website PianetaMilan (Milan Planet), threw a light on how the elections incidentally damaged the Italian heavyweights.

Berlusconi is still Italy's richest man. He could still spend €300m a year on transfers, but his political advisers forbid it. In this era of austerity, it would look frivolous and wasteful.
His aides advise him to splash out during electoral campaigns. Milan bought Ibrahimovic, Robinho and Mario Balotelli before recent elections. But they won't let Berlusconi sell the team or spend heavily too often. Both would lose public favour and votes.

Quite clearly, the repercussions in Silvio Berlusconi's political career had an adverse effect on the club, weakening their balance books. The Rossoneri were steadily on the decline from their celestial grace as one of the major powerhouses in Europe.

In such cases, budget cutting is the only option that presents itself - and AC Milan did choose to make up for the losses by signing mediocre players. However, they could have saved themselves of all that misery and the after-effects that came with it.

He was found guilty of tax evasion in 2013 which incurred heavy monetary losses. As if that wasn't enough, a €560 million lawsuit against the club's chief investors, Fininvest, dented the financial stability.

The summers when it all started crumbling...

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Andrea Pirlo, David Beckham and Ronaldinho

The once mighty Il Diavolo who ruled the transfer market was struggling to find appropriate reinforcements for their legends; A statement backed up by their transfer activities in the summer of 2008.

Engaged vehemently in floundering battles with financial extremities, Milan brought a waning Ronaldinho for €21 million, who arrived at the San Siro amidst a bucket load of expectations after finding himself surplus to requirements in Pep Guardiola's system.

That's it.

The costliest and the only marquee signing they would make that summer. Of course, they brought another well-known personality in Gianluca Zambrotta - another player past his thirties - followed by the loan acquisitions of the suave David Beckham and their former legendary marksman, Andriy Shevchenko.

Berlusconi's supplies were steadily drying up, and that was starkly visible from how the Italians tried to plug the gaps in their squad by signing aged players like Beckham and Shevchenko on loan.

Results, you ask? Finished third in the league, eliminated in the round of 16 in Coppa Italia and in the first round in the UEFA Cup. Perhaps, the only notable thing the spectators about season 2008-09 is Paolo Maldini's final bow as a footballer, the most fabled warrior ever the Rossoneri had the privilege of bragging about in their incandescent chronicles.

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The Rossoneri lost Kaka to Real Madrid in a world record deal in 2009

Season 2009-10 commenced with midfield maestro Andrea Pirlo entering his thirties, behind the fiery and diminutive anchorman Gennaro Gattuso. The club, however, failed to estimate the importance of ameliorating their midfield. They lost their beloved Brazilian prince Kaka that summer, to Real Madrid in a world-record €65 million deal back then, while Dutch hitman Klass-Jan Huntelaar made the reverse move for €15 million.

With Maldini saying his goodbyes, Thiago Silva's arrival was the only notable piece of business Milan would accomplish that summer of 2009. The midfield, however, remained in the dark and wailing desperately to be refined. Another fruitless season fast followed, and the dangers of avoiding a squad revamp were ringing alarmingly more than ever.

Season 2010-11 saw the revolving door of San Siro busy with arrivals and departures. Beckham left, followed by the ineffective Huntelaar. With Silvio Berlusconi hungrier more than ever for the taste of silverware, the club signed the charismatic Zlatan Ibrahimovic on loan, Manchester City flop Robinho, and a promising midfielder in Kevin- Prince Boateng.

The club was hit by an epidemic of injuries with more than most of the starters being sidelined. Berlusconi and co were forced to work again, as they brought in Antonio Cassano and Mark Van Bommel; but those were far from the long-term solutions Milan needed.

Yet, the trifecta of Ibrahimovic, Robinho and Alexandre Pato were enough to help them avoid a third consecutive trophyless season, as they delivered the 18th Scudetto - their first since the 2003-04 campaign.


2012: The year of the Apocalypse

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Zlatan Ibrahimovic was one of the big names to embrace the exit door at Milan in 2012

None in the modern times can aptly explain the term 'living hell' better than a set of Rossoneri devouts. And, to those ardent fans of the red and black devils, reminiscing this vexatious walk down the memory lane might be a carking one.

Massimiliano Allegri, the man who took over the stewardship after Leonardo's departure had delivered a Scudetto to everyone's delight at the club, but the festivities were short-lived. As a matter of fact, they still are craving to be relived.

AC Milan have clinched the Supercoppa Italiana twice in this decade (2012 and 2016), but are yet to end a barren run, a seven-year wait for the Scudetto and move out of Juventus' frightening domination.

2012, if anyone has the faintest reminiscence of, was touted to be the year the world would cease to be; the age of the apocalypse. While the eschatological beliefs were far from being true, the End of Days theory was visibly materializing in Milan.

The Rossoneri had already parted ways mutually with Andrea Pirlo in the summer of 2011. The midfield virtuoso waved sayonara to the club with nothing but a Cartier pen in his hand, apparently a gift from the club for his decade-long service.

365 days later, an exodus would follow.

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Thiago Silva and Alexandre Pato followed Ibrahimovic out of the San Siro

Filippo Inzaghi and Massimo Oddo called time on their careers. Gianluca Zambrotta, Alessandro Nesta, Gennaro Gattuso, Mark van Bommel, Clarence Seedorf; all left for free, bringing in no monetary benefits in the days when they were direly needed.

That's not all, folks. Zlatan Ibrahimovic, Thiago Silva and Alexandre Pato too embraced the revolving door at the San Siro albeit for a combined fee of €78 million.

The legendary star-studded team of AC Milan saw a stark end that year, as names far from being worthy to shoulder and preserve their legacy joined the club. Riccardo Montolivo, Stephan El Shaarawy, Cristian Zapata, Nigel De Jong, Bojan and Mario Balotelli formed the new face of the great footballing institution.

However, they were far from helping the once mighty Il Diavolo who plunged deeper into the abyss, with their hopes for revival diminishing as days passed by.

Milan have undergone a couple of managerial changes ever since the mass exodus that is well-documented in their history books. Giant figures Clarence Seedorf and Filippo Inzaghi, who once ruled over Europe in the red and black shirt, failed to repeat history as the head honchos of the club.

The ardent Milan supporters are yet to savour the music of the Champions League, apparently, the chocolate to every football fan's ears, at the San Siro since it was last heard in 2014.


The end of the Berlusconi era

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Yonghong Li and Han Li completed the takeover of Milan for €740 million in 2017

A single ray of hope, perhaps the brightest in a long period of time, came to pass through when Silvio Berlusconi stepped down as the honorary president at AC Milan. The Italian Prime Minister's bittersweet reign saw the club winning 29 trophies including 5 European Cups, making them the second most successful club in Europe with 7 titles behind Real Madrid.

While Berlusconi sold Milan in a €740 million deal to Rossoneri Sports Investment Lux in April 2017, new owners Yonghong Li and Han Li wasted little time in letting their intentions known to the public.

AC Milan had the finest transfer market of the decade in summer 2017; they roped in 11 players for a cost-effective fee of £146 million. Leonardo Bonucci, Andre Silva, Hakan Calhanoglu, Mateo Musacchio and Lucas Biglia to position themselves as serious title-challengers.

Vincenzo Montella won the Italian Super Cup as the Rossoneri returned to Europe after three years, in the Europa League for season 2017-18. The tactician, however, barely stayed for 18 months before receiving a sack, only to be replaced by another of Milan's old and decorated generals, Gennaro Gattuso.

Off the field, turmoil haunted the club again as their Chinese owner Yonghong Li lost the ownership to Elliot Morgan Corporation. His negligence in keeping up with the loan investment plan of €32 million that aimed at refinancing a €303 million debt, a sum incurred in order to acquire the club ownership from Silvio Berlusconi, proved far too costly.

Rubbing salt to the wound, the Red and Blacks were banned from entering the UEFA Europa League despite a sixth-place finish, on the charges of breaking the Financial Fairplay Rules in the transfer market. The ban, however, was lifted and millions of Rossoneri heaved a sigh of relief.


Gennaro Gattuso: The devil personified

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Can the devil deliver the promised land?

Two of Milan's legendary players, Inzaghi and Seedorf, have fallen short of reviving their beloved club. Yet, that history didn't deter Gennaro Gattuso, the hot-blooded and dauntless lion who once skippered the club, from taking to the mantle as the new gaffer of Milan.

So far, the diminutive Italian has aptly carried on the good work at the San Siro. Though Milan went trophyless in 2017/18, they finished as runners-up of the Coppa Italiana in one of the most exciting Serie A seasons of the decade, thereby keeping the hopes of their resurgence alive.

Gennaro Gattuso is a man capable of entering the pensive thoughts of the most true-hearted and steadfast of Milan's supporters since he has pretty much he breathed them himself. As the fans pin their hopes on his sturdy shoulders, can he, the man who is the literal personification of the devil, relieve his beloved club from the purgatory they have suffered all these years? Can he help Il Diavolo free themselves of the chains of their self-created hell and move out of their own gigantic shadow?

While a tried and true AC Milan cognoscente passes his time brooding over Gennaro Gattuso's potent as a tactician, the world can but pray that the devil liberates them from the agonies of the Inferno and leads them to the promised land, ushering the much-awaited epoch of glory.

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