AC Milan: From Glory to Decline — What Went Wrong?
AC Milan is one of those teams that scream football heritage. The iconic red and black kits, legends like Ronaldinho, Kaká, and Paolo Maldini, and of course, the seven UEFA Champions League titles — the second-most in European football history, only behind Real Madrid.
But whereas Madrid has remained a dominant force both domestically and in Europe, Milan’s fall from grace has been sharp. Since the 2010s, the club’s story has mirrored that of Manchester United following legendary manager Sir Alex Ferguson’s retirement in 2013 — from champions to a club constantly chasing its own legacy.
Part 1: The Fall Begins (2010–2020)
Milan’s 18th Scudetto came in the 2010/11 season. They had a squad packed with stars like Zlatan Ibrahimović, Thiago Silva, and Clarence Seedorf. But the following season, they failed to defend the title and finished second. That was the start of a slow collapse. From 2012 onwards, the decline became obvious. After two more seasons of top-three finishes, Milan dropped to 8th in 2014/15.
That marked the beginning of what fans refer to as the “banter era.” Between the 2014/15 and 2018/19 seasons, Milan finished outside the top four for five consecutive years. They posted their worst league finish in 2014/15, ending the season in 10th — a position that summed up just how far they had fallen.
In 2017, Vincenzo Montella was sacked due to poor performances. Gennaro Gattuso, a club legend, was appointed as head coach. Gattuso managed to bring some stability. Milan finished 6th and qualified for the 2018/19 Europa League, but even that was nearly taken away due to FFP (Financial Fair Play) violations. Milan appealed to the Court of Arbitration for Sport and won the right to compete.
Gattuso’s first full season in charge (2018/19) saw Milan finish 5th, missing out on Champions League qualification by a single point. Despite the progress, Gattuso resigned at the end of the season. Marco Giampaolo was brought in on a two-year contract. However, Giampaolo lost four of his first seven matches. Fans quickly lost faith, and he was sacked after just four months.
Stefano Pioli was then appointed. His initial impact was the classic “manager bounce” — Milan went on a 10-game unbeaten run (7 wins, 3 draws). Pioli was rewarded with a two-year extension. In his first full season (2020/21), Milan finished 2nd in Serie A — their highest position since their title win in 2010/11 — and returned to the Champions League for the first time since 2013/14.
In the 2021/22 season, Pioli did what no Milan coach had done in a decade: win the league. Milan won their 19th Scudetto with a club record 86 points. Everything seemed to be back on track, but the cracks would soon appear.
Part 2: Cracks Beneath the Revival (2022–2023)
The following season (2022/23), Napoli — led by a resurgent squad under Luciano Spalletti — stormed to the title. Milan couldn’t defend their crown. They still managed to finish top four, but the gap to 1st was a massive 20 points. In 2023/24, they improved slightly, climbing back to 2nd, but again the points gap to Inter Milan (who won the title) was 19 points.
The result was that even when Milan were in the upper half of the table, they weren’t really competing. By the end of the 2023/24 season, Pioli and the club agreed to part ways. He left with dignity — the most successful Milan manager of the past decade — but his exit opened the floodgates.
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Part 3: Ownership Shifts, Maldini’s Dismissal, and Zlatan’s Power Grab
To understand how Milan went from a title-winning side to chaos, you need to look at the ownership structure. Back in 2016, during a wave of Chinese investment in football, AC Milan was sold to Sino-Europe Sports Investment Management Changxing Co.
By April 2017, Rossoneri Sport Investment Lux became the new parent company. The plan was for a consortium to take over, but in reality, it was largely one man — Li Yonghong — who didn’t have the financial muscle to sustain Milan. He took out a massive loan from American hedge fund Elliott Management to close the deal, but by July 2018, he defaulted on a €32 million installment.
Elliott took over control of the club. Known for restructuring failing assets, Elliott’s goal wasn’t to restore Milan’s legacy out of passion — it was about turning a profit. Paul Singer, the head of Elliott, is an Arsenal fan and a ruthless businessman. He brought in key figures like Ivan Gazidis, Frederic Massara, Hendrik Almstadt, Geoffrey Moncada, and perhaps, most importantly, Paolo Maldini.
Milan’s operating costs were slashed. The transfer strategy focused on young, undervalued players with high resale value — such as Rafael Leão, Franck Kessié, Theo Hernández, and Ismaël Bennacer. That approach worked: Pioli was retained instead of appointing Ralf Rangnick, a decision that paid off.
Milan returned to the Champions League, then won the league. However, even during this renaissance, the warning signs were there: Milan finished bottom of their Champions League group, and nearly 40% of league goals came from Olivier Giroud and Zlatan Ibrahimović — two veterans with a combined age of 75.
In July 2022, RedBird Capital Partners acquired AC Milan for $1.3 billion, with Elliott retaining a minority stake. RedBird’s early tenure didn’t inspire confidence. In their first season (2022/23), Milan failed to defend their title and finished 4th — 20 points behind Napoli. In 2023/24, they improved to 2nd but still lagged far behind Inter.
Then came the big shifts. CEO Ivan Gazidis left in December 2022. Paolo Maldini, who had helped rebuild the club, was sacked. The reason? Allegedly, two poor transfer windows. In reality, Maldini was critical of the ownership and refused to be a yes-man. His last major signing was Charles De Ketelaere — a player who failed at Milan but became a star at Atalanta.
After hanging up his boots, Zlatan Ibrahimović was appointed as a club advisor. He had a fallout with sporting director Antonio D’Ottavio, who was eventually sacked. When asked about his role, Zlatan told The Athletic: “To bring results, to bring up value, and to make things better with an ambition to win.”
Zvonimir Boban — the man who originally brought Zlatan back as a player — criticized him, saying: “I don’t know what he does, I don’t get it.” On Sky Sports Italia, the two clashed as Zlatan said, “I’m the boss, everyone works for me.”
Zlatan’s attitude was a sharp contrast to Maldini’s role, which was to act as a bridge between the fans and the board. Zlatan openly said he worked for RedBird at AC Milan, not AC Milan itself. This only deepened the disconnect between the club and its supporters.
Part 4: Fan Revolt, Transfer Failures, Fonseca’s Collapse, and Conceição’s Chaos
RedBird’s approach further angered fans. Gerry Cardinale said in an interview: “In America, the one who spends the money owns the club. In Italy, the fans think they do.”
That quote was all fans needed. During Milan’s 125th anniversary match against Genoa, banners were unfurled: “Players without hunger or dignity, you perfectly represent these owners. Incompetent directors, club without ambition — you are not worthy of our history.”
On the management side, Giorgio Furlani replaced Ivan Gazidis as CEO. Furlani, known more for finance than football, reportedly asked club legend Andriy Shevchenko if he had played for Milan. He was also responsible for sacking Maldini.
On the pitch, the squad turnover was brutal. Only four players from the 2021/22 title-winning starting XI remained. Recruitment post-Maldini was disastrous. Four new strikers — Luka Jović, Tammy Abraham (on loan), Álvaro Morata, and Santiago Giménez — flopped. Morata, who scored just five goals, later admitted joining Milan was a mistake before being loaned out to Galatasaray.
Defensive reinforcements didn’t fare better. Emerson Royal joined for €15 million despite a poor spell at Spurs. Milan ended up signing 34-year-old Kyle Walker on loan from Manchester City. While decent, he was never a long-term solution. Portuguese coach Paulo Fonseca was brought in after Pioli’s exit, but he was never the board’s first choice — rumors pointed to Julen Lopetegui.
Fonseca had Zlatan’s backing but little fan support. He tried asserting authority by benching Rafael Leão and Theo Hernández for poor performances. They came off the bench and assisted an equalizer versus Lazio. Worse still, a viral photo showed Leão and Hernández ignoring Fonseca during a water break team talk. Theo later said, “We had just come on; we didn’t need a water break.”
Despite their excuses, the image stuck. It summed up Fonseca’s loss of the dressing room. The end came after a 1-1 draw with Roma. Fonseca wasn’t even aware he had been sacked until after the post-match interview. When reporters followed up, he confirmed: “Yes, it is true. I’ve exited Milan. That’s life.”
He was replaced by Sérgio Conceição — former Inter player and FC Porto manager. Conceição started strong, beating Juventus and Inter to win the Supercoppa Italiana. A video of him lighting a cigar in the locker room made the rounds. It looked like a new dawn.
But the bounce didn’t last. Milan stumbled to a 1-1 draw against Cagliari days later. Morata left the club, and the club’s form dipped again. They were eliminated from the Champions League by Feyenoord — who were later comfortably beaten by Inter in the next round. In the Coppa Italia final, Milan lost to Bologna. To rub salt in the wound, former Milan captain Davide Calabria lifted the trophy — while on loan at Bologna.
Part 5: Financial Wins, Footballing Losses — Is Milan Entering Another Banter Era?
Despite all the turbulence on the pitch and in the boardroom, AC Milan has become economically stable under RedBird’s ownership. The numbers are impressive: commercial revenue rose 72%, growing from around €100 million to nearly €180 million. Total revenue jumped from about €270 million during their title-winning season to approximately €490 million last season.
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Milan also posted back-to-back profits — something they hadn’t done since 2006/07, when their positive balance was largely due to the €45 million transfer of Andriy Shevchenko to Chelsea. That’s nearly two decades of being in the red. Much of the recent profit has come from player sales. The most notable being Sandro Tonali’s €70 million move to Newcastle, which was booked as pure profit.
However, this short-term financial gain came at a long-term cost to the team’s strength on the field. AC Milan now has one of the lowest wage bills among Italy’s “big three” clubs, and one of the lowest wage-to-turnover ratios in Europe — hovering just above 45%. Their gross debt, which once soared above €250 million, is now around €100 million — lower than even clubs like Genoa or Sassuolo.
But there’s a looming problem: Milan’s current financial model has depended heavily on three things — Champions League football, high player sales, and record matchday attendance. In the 2024/25 season, they will miss out on all European competition after finishing 8th in the league. That’s not just a sporting failure — it’s a financial one, too.
Gerry Cardinale has pointed to Liverpool as a model to follow. He said: “There’s a great example of how there’s been an evolution — Liverpool. They managed to find a compromise between the sports side, the business side, and the ownership side. That’s exactly what you should look at and try to replicate elsewhere.”
But the truth is, AC Milan today resembles Manchester United far more than Liverpool. A club with a historic legacy, out-of-touch ownership, over-focus on commercial growth, lack of footballing vision, frequent managerial turnover, and discontent among the fans.
With no European football, key players doubting the project, and no clear path forward, Milan now stands at a crossroads. Either the leadership at RedBird changes course and starts prioritizing the sporting project, or the club could enter a second banter era — one defined not by rebuilding, but by stagnation, short-term fixes, and long-term decay.
One thing is clear: for a club with Milan’s legacy, the current state is unacceptable. And unless something shifts soon, the future may look a lot more like the past — and not the glorious kind.
By: Sekwila Mumba / Instagram: https://www.instagram.com/s3kwila
Featured Image: @GabFoligno / Image Photo Agency / Getty Images