Sleeping giant AC Milan and their ‘life changing’ quest to return to Champions League football

Back in the 1980s, AC Milan were a mess. They were demoted to Serie B for the first time in their history in 1980 as punishment for their involvement in the Totonero scandal, a system of illegal gambling and match-fixing. They won promotion, were relegated and fought their way back to the top flight again over the next four years, but were on the verge of being declared bankrupt when Silvio Berlusconi arrived in February 1986.

He invested vast sums of his personal wealth, instantly transforming the club as he appointed Arrigo Sacchi as Coach and signed Dutch internationals Ruud Gullit, Marco van Basten and Frank Rijkaard. With a homegrown spine that included iconic names like Paolo Maldini, Franco Baresi and Alessandro Costacurta, the Rossoneri would go on to enjoy a period of domination that had never been seen before.

Trophies arrived both at home and abroad, Milan becoming instantly recognisable and eventually one of the most feared teams on the planet. Managers and players came and went, Fabio Capello, Carlo Ancelotti and Max Allegri all took a turn on the bench, but still the silverware piled up. George Weah, Andriy Shevchenko and Kaka among the stars who delivered unforgettable memories to fans as they packed the cavernous San Siro to capacity week after week.

Then just like that, it was over. Berlusconi’s problems have been well-documented, but he essentially stopped bankrolling the club and they slumped into mediocrity, signing players well past their prime and cycling through inexperienced and ill-suited coaches at an alarming rate. Former players Clarence Seedorf and Pippo Inzaghi tainted their legacies as players by attempting to manage the side, while transfer guru Adriano Galliani completely lost his touch when it came to acquiring players.

Talk of a takeover dragged on for almost two years, deals collapsing and buyers like Bee Taechaubol vanishing when they seemed set to save the Rossoneri. Then finally Chinese entrepreneur Li Yonghong managed to put together the funds to buyout Berlusconi, but after so many false dawns and delays, few knew what to expect once the 2016/17 campaign came to an end. 

Yet Li has wasted no time in proving just how serious he is, authorising a spending spree that is eerily reminiscent of the club’s 1990s heyday. Just as Galliani and Berlusconi had reignited a downtrodden fan base three decades earlier, the work of new sporting director Massimiliano Mirabelli has proven impossible to ignore. 

Deals for players were concluded at breakneck speed, the club determined to give Coach Vincenzo Montella a strong and competitive squad right from the start of pre-season training. Mateo Musacchio, Ricardo Rodriguez and Andrea Conti will join Alessio Romagnoli at the back, a quartet of excellent defenders that cannot fail to improve upon the performances of predecessors Gabriel Paletta and Cristian Zapata.

In midfield, Atalanta’s Franck Kessie – a target for a number of Premier League clubs – was quickly snapped up and will bring some much needed energy and drive in the middle of the park. Hakan Çalhanoğlu has arrived to deliver his set piece wizardry, while in attack Portuguese star Andre Silva will be expected to provide goals as the focal point of Montella’s favoured 4-3-3 system.

Every position on the field has been reinforced and every signing – perhaps even the arrival of Fabio Borini – makes sense. Mirabelli and Montella have clearly and methodically planned their approach, identifying players they want and working tirelessly until they land at Casa Milan holding a red-and-black scarf.

Mino Raiola has been the only dissenting voice, asking loudly where the money is coming from and just how sustainable the spending is over a longer period. Of course, the self-styled “super agent” is doing so with his own interests in mind, his client Gianluigi Donnarumma locked in a bitter contract dispute with Milan.

With just twelve months remaining on his current deal, the club is keen to tie the 18-year-old down and secure his services, recognising that he is potentially the cornerstone of this exciting new side. Just as Baresi and Maldini were in the past, Donnarumma could have been the Italian heart of a powerful Milan team, the homegrown duo always the most beloved of players no matter how many Ballon d’Or winners arrived to feature alongside them.

Instead, the crass wrangling of his agent has burned those bridges and it is unlikely that the goalkeeper will ever truly win back the affection of those in the stands who had championed his meteoric rise. Donnarumma has backtracked over his demands to leave and it seems he will sign a new contract in the coming days, but even that will come with a cut-price buyout fee in case the Rossoneri fail to qualify for the Champions League.

That stipulation will only add to the mistrust supporters now see in their prodigious young star, but it also highlights the fact that Milan are making a huge gamble on their ability to secure a berth in Europe’s most lucrative tournament. UEFA have already expressed their concerns over the club’s compliance with their Financial Fair Play Regulations, with the response from new general manager Marco Fassone focussing fully on the income it would generate by getting back to the competition it once dominated.

“If we want to bring AC Milan to compete with giants of world football, we will have to double our revenue and perhaps more,” the Milan official told a press conference shortly after being appointed. "With the new formula of the Champions League, being there or not being there is life changing. We're talking about clubs that qualify for the knockout stages, not only those who reach the final. It already means a lot in terms of cash, as a low estimate it’s €50 million of revenue per year.”

He will be fully aware that Serie A will have four teams automatically in the group stages in 2018/19 and Fassone, Li, Mirabelli and Montella appear to be backing their ability to secure one of those places. The ramifications if they fail could be fatal, but if the new signings gel and the Coach can continue his own impressive work, perhaps the team whose colours look like a roulette wheel are right to gamble. Bet it all on red and black.