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The summers when it all started crumbling...
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.
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
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.
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
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
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.
