Once upon a time not so long ago, Italian heavyweights AC Milan were thriving at the heart of domestic and European glory.


Holding the keys to some of Europe’s most elite, the Guiseppe Meazza was simply the prime destination for the internationally famed.

Real Madrid v AC Milan - UEFA Champions League

In a recent attempt to return to their former glory, significant investment has since been shot through the veins of the Rossoneri... without the desired effect.


The latest setback came in Milan's humiliating Europa League group exit at Olympiacos, stretching their last domestic or European title to eight years - as this article delves into the plight of the Rossoneri’s once untouchable force.


The Glory Years


In a two-way battle with ​Juventus, European dominance in Milan stretched across two decades between 1990 and 2010. The 1990s saw them scalp five Scudetti and a Champions League title, with the likes of Marco Van Basten and Ruud Gullit shining.


In fact, they would become the first team in Italian top flight history to go an entire season unbeaten on their way to a 12th Scudetto in 1991/92, as their famous attacking philosophy and pivotal youth infrastructure began to take hold.

Paris Saint-Germain's Brazilian midfielder Ra? (L)

Trio Paolo Maldini, Franco Baresi and Demetrio Albertini twinkled under the floodlights of San Siro, in a spiral of home grown talent amidst an unprecedented trophy haul.


Although the turn of the millennium proved somewhat less endearing, the Rossoneri would then play home to two of their most influential players of all time. Among feared greats, including Andrea Pirlo, Filippo Inzaghi and Andrea Nesta, it was the names of Kaka and Andriy Shevchenko that proved integral. 


Shevchenko would finish Milan’s highest goal-scorer in six of his seven campaigns, notably scoring the winner against rivals ​Juventus in the 2002/03 Champions League final.

AC Milan's Ukrainian forward Andriy Shev

His Brazilian counterpart would fire his side to a Scudetto and UEFA Super Cup in his maiden year, scooping Serie A Player of the Year along the way, as both placed their names in Milan folklore.


Although they would play in Milan's famous Champions League final loss to ​Liverpool, Kaka would later help avenge their defeat to the Reds in 2006/07. However, no-one could have anticipated the plight of Italy’s most decorated force.


The Rossoneri would have to wait an agonising seven years for any means of success in 2010/11 – an 18th Serie A title triumph that was meant to re-ignite their renowned stature.

UEFA Champions League Semi Final: Manchester United v AC Milan

Instead, rivals ​Inter and Juventus would obliterate any hope of returning to former glory by winning 13 of the next 14 Serie A titles, as they wilted beyond the belief of their faithful following.


Lowly Finishes & Financial Mismanagement


A spate of disappointing domestic finishes, culminating in the sacking of six different coaches, left the daunting task of former Rossoneri Gennaro Gattuso - to turn around the club's fortunes in November 2017. 


Meanwhile, substantial investment in excess of £200m under former Chinese owner ​Li Yonghong, including the acquisition of former Old Lady defender Leonardo Bonucci, would eventually see Milan return to European competition after a beleaguered four year absence.

AC Milan Press Conference

Yet, their hopes of a first European triumph for over 10 years were dashed against Arsenal in the round of 16 stage, as Gattuso’s valiant attempt to galvanise the squad failed. 


Whilst Bonucci returned to Juve after just ​one season, a sixth successive finish outside the top four in Serie A was further compounded by Li Yonghong’s failure to pay a series of ​debts equating to £32m, leaving a financial void.

In a desperate attempt to rekindle the Rossoneri, US Hedge Fund Elliot Management took control of ownership in August 2018, overseeing eight new signings that included duo ​Gonzalo Higuain and Mattia Caldara.


The high profile signings looked positive on paper, yet none would have an impact as Caldara would suffer a long-term achilles injury, whilst Higuain's contribution would prove inept.


Despite finding themselves fourth in Serie A after 16 games, pressure to return to former European heights once again faltered.

Bologna FC v AC Milan - Serie A

​Eliminated on the penultimate matchday by Olympiacos, the Greeks and Spain's Real Betis would pip Milan to last 32 qualification, leaving fans around the continent bewildered at yet another catalogue of failures.


So Where Do AC Milan Go From Here?


The Italian giants were ​hi​t with a one-year Europan ban last summer, after breaching FIFA's Financial Fair Play Regulations under Yonghong.


Likewise, on the field matters leave Gattuso scrambling for answers, as it remains increasingly unclear as to the timing of Milan’s next trophy in a quite frankly, horrendous era. 

FBL-ITA-SERIEA-MILAN-TORINO

Whilst a potential top four finish could somewhat prove a distraction, questions at the club are circling viciously, if they weren’t previously.


Already 19 points off their leading counterparts, one thing is for sure, it will take a transformation to fix the seven-time Champions League winners - currently free-falling in their predecessor’s shadows.