Once one of the most dominant teams in Europe, AC Milan have fallen from the top. The 18 time league champions last won Serie A in 2011 and finished the 2018/19 campaign at fifth.
But how did things go so awry? How did one of the most decorated clubs in Europe become one that is not even good enough to play in the Champions League? A lot of factors including ownership trouble, reckless spending, managerial instability and bad squad management have contributed to AC Milan's downfall.
Debt and destruction
Silvio Berlusconi's ownership from 1987 to 2017 saw the club dominate world football, out-spending their neighbours. But the decline started when he opted to focus on his political adventures and stopped investing in the club. The lack of investment resulted in huge amounts of debt and the inability to properly rejuvenate the squad.
Chinese businessman Li Yonghong bought the club in 2017 and promised huge investment. He spent over 190 million Euros in transfers, bringing the likes of Leonardo Bonucci, Andre Silva and Hakan Calhanoglu.
But Li's ownership would be short-lived as current owners Elliot Management would take over after Li failed to pay back their loan. Current president Paolo Scaroni took office in 2018 and under him, the club spent 291 million Euros in transfers so far.
The money spent by Li and Elliot Management was too much and the club was banned from European football as it failed to balance its books. Notable players brought during this period failed to deliver and results on the pitch didn't improve.
Massimo Allegri delivered the 2010/11 Serie A league title to the San Siro and finished second and third in the following seasons. After major departures in the 2012/13 season, it became difficult for Allegri to maintain Milan's competitiveness.
Club legend Clarence Seedorf replaced him in January 2013 and steered the club into eighth position. Seedorf would be replaced by Filippo Inzaghi, who finished tenth in the 2014/15 season. He was then sacked in favour of Sinisha Mihajlovic.
Mihajlovic finished seventh and reached the Coppa Italia final. Vincenzo Montella replaced him the following season and delivered European football by finishing sixth.
Gennaro Gattuso would replace Montella in November and his time at the club would see them finish sixth and fifth. But he would leave on May 28, 2019, and Stefano Piolo would be appointed.
Apart from Gattuso, no other manager would have more than two seasons at the dugout, citing a lack of vision and philosophy from the club's hierarchy. This managerial instability has accelerated the club's decline.
Poor squad management
AC Milan's lack of vision and future planning has affected their transfers as well.
In the 2010/11 title-winning season, Milan had a very ageing squad with the likes of Gennaro Gattuso, Alessandro Nesta and Andrea Pirlo. Allegri opted for instant success, ignoring the youth which backfired massively.
The 2011/12 season saw youth players Sokratis Papasthathopoulos, Pierre-Emerick Aubameyang and a 32-year-old Pirlo leave the club. The club only managed to get 5.8 million Euros for these 3 players combined.
Sokratis became one of the top defenders of the world in his time at Dortmund, and Aubameyang is one of the most prolific goalscorers in modern football, while Pirlo aged like fine wine at Juventus.
Thiago Silva and Zlatan Ibrahimovic left the club in the 2012/13 season along with failed wonderkid Alexandre Pato.
The club tried to replace their title-winning squad with less than average players and ignored their youth. This lack of future planning declined the club further.
Transfer that didn't work
Due to their financial troubles, AC Milan were forced to become a selling club. They tried to replace players like Zlatan Ibrahimovic, Thiago Silva, Kevin Prince Boateng, Andrea Pirlo with average mid-table players. Even when they tried to spend big, it didn't work out.
Mario Balotelli was brought in from Manchester City to replace the ageing Zlatan Ibrahimovic and failed. The club failed to replace any of their major players.
Under Li, the club spent big and brought Leonardo Bonucci from Juventus for 42 million Euros and Andre Silva for 38 million Euros but both of them failed at the San Siro.
Elliot Management also tried to spend big with the likes of Lucas Paqueta, Krzysztof Piatek but like Li before them, failed.
The transfers made by the club were ambitious but ultimately failed to hit their mark.
At the time of writing, AC Milan sit seventh in Serie A.The expensive transfers that they tried over the years, failed and the club depends on its youth.
They are no more than a shadow of their former glorious self. But under the ownership of Elliot Management, the club is financially stable. With proper investment and philosophy, AC Milan can surely return to the pinnacle of world football. But this process will be a long one.