Tuesday marked exactly 1,000 days since RedBird Capital Partners acquired a majority stake in AC Milan from Elliott Management.

While the celebrations for the 19th Scudetto were continuing in the Piazza Duomo, a then-mysterious figure emerged, photographed among the masses. His name is Gerry Cardinale, and those stood around him at the time had no idea of what was to come in the next three years.

RedBird bought Milan from Elliott Management ahead of the 2022-23 campaign and it was already known back then that it would be an even more important season in the tapestry of the Rossoneri’s resurgence.

The hope was that winning the Scudetto was not an end point but rather a starting gun, one that brought fresh impetus to the plans of the ownership. When the very top of the club changed, there were question marks – from ourselves as well – about whether it could disrupt the stability.

Mission statement

As mentioned, it is exactly 1000 days ago on Tuesday that Cardinale officially became a majority shareholder of Milan via RedBird, and he introduced himself in a very bold way.

“Our vision for AC Milan is clear: we will support our talented players, coaches and staff in their efforts to achieve success on the pitch and to enable our fans to share the extraordinary experiences of this historic Club,” he said.

“We will ensure that we leverage our global sports and media network, our expertise in data collection and analysis, our track record in the development of sports stadiums and hospitality to achieve one goal: to keep AC Milan at the top of European and world football.”

However, there is one phrase that Cardinale said not too long into his tenancy that struck a chord with the fan base, and not for the right reasons. Speaking at Technology’s ‘Investing in Global Sports’ seminar as part of their Sports Analytics Conference, he made alarming statements.

“One of the things that surprised me is that Milan has the second most number of Champions League trophies after Real Madrid. I hadn’t really kept up with that,” he said.

“But it’s an undermanaged asset. Serie A has a right to have a seat at the world table and Milan have a right at that table. It’s our job to do that.

“In sport, you can’t buy championships. I would obviously like to win the Scudetto and the Champions League every year, but if we did it would be contrary to our job.

“Our job is to get a return on this investment and if every year the same people win it wouldn’t work, right? It would make the evaluation completely dilutive.”

These are not exactly the words of someone driven to win every competition that the club are involved in, especially if it were to even slightly rock the economic balance and the vision of self-sustainability.

Transition to ‘entertainment entity’

During his time at Milan, Cardinale has almost lived three lives. The first was his first year, in which he rarely made an appearance, staying out of the way and observing the Rossoneri’s methods.

The second, currently still active, started in the summer when he decided to part ways with Paolo Maldini and Ricky Massara (more on that to come). After that, he was certainly much more present and engaged with the media too.

Just as Cardinale adapted to his new environment, so did Milan. Innovation is the word that RedBird liked to use when describing their work with the club, effectively trying to ‘modernise’ the club to turn it from just a football team to a media entity.

A lot of focus was put on the commercial side of things and continues to be, as seen by various partnerships with the New York Yankees, Off-White, New Era, Main Street Advisors and others. Under the new owners, the idea was to see Milan grow globally as a brand above all else.

He would go on to speak in an interview with Harvard Business School as part of a document which analysed the club and the transition to ownership by a US-based fund.

“When we bought AC Milan, a lot of American sports team owners called me and said, ‘You’re crazy.’ They said, ‘You can’t do business in Italy,’ and ‘It’s impossible to make money in European soccer.’ Most people who invest in sports clubs do it because they’re emotionally invested.

“They put winning trophies above everything else, and that often leads them to make the mistake of thinking that spending too much to field a team of stars is linearly related to winning. But that’s the worst thing you can do as an investor.

“We bought it for a figure that corresponded to 3.6 times the revenues of the club; the new owners of Chelsea FC bought it for a multiple of seven times the revenues when you consider the earn out.

“I brought the New York Yankees with me for a small minority stake, given our long-standing partnership with them and our desire to bring the best practices of American sports to Italy. I think Milan has the potential to become a €5bn company.”

Further proof of the mission statement: financial and brand growth is first, and if winning comings along with that then happy days. The latter, however, was never the priority.

Fading ‘Milanismo’

Concerns began to arise that Milan had moved from a successful and winning organisation – as shown by the 2021-22 Scudetto and the 2022-23 Champions League semi-final run – to one that was on a slippery slop.

At the start of the the 2023 summer window, Cardinale decided to sack Maldini and Massara, putting CEO Giorgio Furani and chief scout Geoffrey Moncada – promoted to technical director – at the top of the hierarchy.

Of course, this didn’t go down well with the fans. We wrote at length about the developments at the time, and about how Maldini’s ‘Milan first over everything’ approach and demand for more control caused a souring relationship to reach a bitter end.

The situation got even more heated with the sale of Sandro Tonali to Newcastle for €70m, given that the midfielder was a fan favourite and a boyhood Milan fan. Not to mention the fact that he’s a very good player, of course, and is now shining for the Magpies.

Worries about RedBird’s plan for the future only escalated with what followed. The famous ‘replace him in the aggregate’ line from the film was applied after Tonali’s sale, with Tijjani Reijnders and Christian Pulisic being the only real hits of the summer spree that followed.

It became very clear from Cardinale’s regular interviews that he wanted Milan to make the most of statistics and algorithms, with the Moneyball protagonist Billy Beane involved. And with that, he has been criticised for not understanding how Italian football works.

There was even an article from the French source FootMercato, suggesting that there was internal friction with regard to the ‘NBA model’ Cardinale has planned for the Rossoneri and how it was not compatible with the pre-established ecosystem of calcio, with all its complexities and stubbornness.

Zvonimir Boban summed things up well in the eyes of many on Andrea Longoni’s podcast in which he spoke about the signings he almost got over the line and the sacking of Paolo Maldini. You can read it in full here, while below is an excerpt about the feeling of belonging.

“I spoke about ‘de-Milanisation’, that was the fear. And it was clear that they wanted to make people lose that strength of wanting to belong. Because it is too big an emotion for someone who wants to control things differently. ‘Always Milan’: what the f*** does that mean?

“The whole world knows what Milan is, they even put ‘Always Milan’ on the bus. Please… Obviously it annoys, it flattens, it almost makes you become a robot. The idea is that, that the fans become customers, the players become assets. And so on, this is their way.

“Maldini’s sacking? A shameful page, done in a shameful way. Indecent, unacceptable and I could say a thousand other bad things. Above all, inexplicable even for them. For them Paolo represented the last obstacle to do what they wanted.

“And the Tonali thing had a big impact, Paolo would never have let him go. We are looking at a difference of 70 million, I don’t know how much specifically. A lot of money but that should never have come to Milan because Tonali shouldn’t have left Milan. Because the boy is a Milan fan.”

Internal power struggles

So, an American-based fund might not be entirely clued up on what it takes to establish a winning model and culture in Italian football, but with the right people in place the correct advice can follow to build such a structure.

The problem is that after Maldini and Massara’s unceremonial farewell, a power vacuum opened up that three figures rushed to fill without actually being qualified to do so. Thus, a great power struggle emerged inside the management.

It was once again Footmercato who painted a grim picture of life inside the walls of Casa Milan. They stated that the Milan management was ‘more than ever divided into several camps’ and on crucial issues that concern the steering of the ship moving forward.

The French outlet claimed that the CEO Giorgio Furlani and RedBird Capital Senior Advisor Zlatan Ibrahimović were ‘tearing each other apart’. There was talk of an ‘internal clash between directors’ currently being witnessed within the Rossoneri ranks, with Ibrahimović being ‘questioned more than ever’.

For example, Furlani reminded everyone before the Lazio game who is in charge, stating: “All decisions pass through me.” This was as a response to the fact that Zlatan had proclaimed himself ‘the boss’ within Milan.

Ibra meanwhile is believed to have lost a lot of support internally during recent months, and he was/is Cardinale’s right-hand man. One thing his detractors point at is his decision to give another accomplice in Jovan Kirovski a job with Milan Futuro, who are having a dreadful debut campaign.

Showing up at events like Sanremo Festival or Formula 1 Grand Prix has not done anything to ease the concerns that Ibra is simply focused on PR rather than building the best possible Milan. It is not too dissimilar to how the ownership were acting.

The result of the aforementioned squabble, which now seems to be a bit calmer, is that Furlani has flew to the United States flanked by lawyers to remind the owner Cardinale who is actually in charge among the directors.

The shadow of Elliott and the Middle East

Why does Furlani have so much sway? Well, in addition to the fact he remained the CEO after the sale (following Ivan Gazidis’ departure), there is the vendor loan factor.

When Gerry Cardinale bought AC Milan from Elliott Management in 2022, he only paid €650m for a deal that was valued at a total of €1.2bn. The remaining €550m was transformed into a so-called vendor loan, granted by Elliott to RedBird, with an interest rate of around 7%.

In recent months, with the repayment deadline set for August 2025, there has been a great debate regarding the vendor loan and whether Cardinale would be able to repay it. All kinds of potential solutions were touted in the media, including the possible sale of a minority stake.

As announced by the club in December, however, said loan has been refinanced until June 2028. That gives RedBird and Cardinale an extra three years to be able to find the money to pay it off.

Finance expert Alessandro Giudice explained at the time why it was something that worked for both parties. However, there still continues to be a bit of fog shrouding the ownership situation moving forward. Will the loan be paid off in full, or will external investment be required to help?

Speaking on Carlo Pellegatti’s YouTube channel, Carlo Festa – a writer for Il Sole 24 Ore – recently cast a further shadow on the future.

“There is no process underway, but there is certainly an interest in evaluating subjects that can bring new finance, therefore new money, into the coffers of Cardinale who, as you know, made this acquisition with debt,” he said.

“He bought Milan for 1.2 billion with almost 700 million in financing from Elliott. This financing was then reduced over the course of these months with the repayment of 170 million, therefore towards Elliott it went down to almost 500 million.

“So, what does that mean? He always finds himself with a very high debt, and therefore he is looking, but he was already doing it before, then this process slowed down, he is evaluating equity partners.

“It is also well known that in these weeks he is in Qatar, in that area where there are the only investors interested in Italian football today. Between Qatar, Bahrain and Saudi Arabia there is possibly money for Italian clubs and therefore possibly also for Milan.

“Cardinale is a very silent shareholder. It seems to me that since September he has not revealed himself. This is because for him Milan is not a sporting affair, but a pure and simple business. Let’s say he does not reveal himself, he does not show himself, he does not give interviews also because his management is very financial.

“What I predict is that he will evaluate possible partners, obviously to a partner who enters in the minority you cannot deny an option to then purchase the majority later, but it is certainly more than a hypothesis. They are detailed rumours that say precisely that he is evaluating a partner, an activity that he had already previously studied.”

Stadium project

Cardinale made it clear from day one that he saw Milan as a club capable of growth, and a new stadium is certainly at the helm of that. However, nearly three years on from their arrival, there are still no spades in the ground.

During his interview on the Bloomberg podcast The Deal, which you can also read in full, Gerry Cardinale spoke about Milan’s stadium plans. After suggesting it in a previous interview, he now confirmed his intentions to create a company to build more stadiums in Italy.

“It will be the first stadium built in Italy since 2011, an American-like stadium with 70,000 seats. We are going to bring music to Milan and build a live entertainment campus, which will be anchored by the team.

“You know, something like AC Milan, it’s interesting because we are going to need to find a way to crystallise value there. But, I mean, that [a stadium] is something that you should probably own forever. That is as iconic as it gets.

“We are going to build this new stadium, and when we are done building that stadium, I promise that we will have a company out of that to build other stadiums.”

After the initial joint project with Inter to build a ‘new San Siro’ launched in 2019, Cardinale and co. went a different route. Land was purchased at a site in San Donato, down in the south east of the city. For some time after, it seemed that the Rossoneri were favouring a move away from San Siro.

Things went quiet while president Paolo Scaroni continued to contradict himself every single time he spoke about the stadium plan in the media. San Donato went from Plan A to Plan B on each occasion he opened his mouth.

Fast-forward to March 2025, Milan and Inter announced a joint bid for San Siro and the surrounding areas. The intention is to partly demolish the existing stadium and then to build a new one on the adjacent parking lot, as part of a wider-ranging investment that includes real estate.

As a result of this, the Diavolo would ‘abandon’ the San Donato project they committed around €55m to, permitting that the council accept the proposal from the clubs. If not, we might well be back to square one, or whatever square they claim to be on.

Italian bureaucracy deserves some blame for the lack of movement on the stadium front, but it undoubtedly went from RedBird’s flagship plan for Milan to a source of embarrassment.

The accounts

While things were up and down (mostly down) on the field, RedBird – headed of course by the commercial team – were at least making positive strides on the financial side.

Milan made a profit of €6.1m on revenues of €404.5m in 2022-23 after a loss of €66.5m had been reported in 2021-22, so that was certainly a marked improvement and a leap forward in the self-sustainability mission.

The following year, 2023-24, the Rossoneri’s net profit for the 2023-24 season was €4.1m, marking the second consecutive year of profit for the club. This profit was achieved despite a €40m decrease in combined audiovisual and ticketing revenue due to a weaker performance in European competitions.

The club’s revenue reached a record €457m, with a 13% increase compared to the previous year. however, all of this should have served to provide a platform from which to build, and what has happened in the last financial year threatens to undo a lot of good work.

As Calcio e Finanza write, the accounts are in the red for this season, for the first time in two years, and the expectation is that the losses will stand at around €25m. The exact reasoning will be fully revealed in the accounts, but it is obviously down to increasing costs and declining revenues.

Things could change with the season ‘ending’ on June 30, so the mercato will have an effect, probably. However, it is definitely not a good sign if the books are balanced by sacrifices like the sale of Reijnders to Manchester City.

In that Harvard Business School paper, Cardinale took a swipe at Inter’s old owners Suning, stating: “They won the Scudetto last year and then went bankrupt: is this really what we want?!”

With no involvement in European competitions in 2025-26, there is a worry that things could further spiral with a further €80-100m gap in revenues. Those words have, unfortunately, aged like milk.

Protests and hope

Everything seemed to come to a head on Saturday night, which was the game closest to the 1,000-day marker for RedBird Capital. While a 2-0 win over Monza was played out on the field, the real headlines were away from the pitch.

It started at 17:00 CEST when thousands of fans gathered at the club’s Casa Milan headquarters to protest, calling for the return of Paolo Maldini. Then, there was a further show of discontent after 15 minutes of the match as fans – the Curva Sud above all – led a mass walk-out.

It made worldwide news. The Athletic had a piece headlined: ‘Milan ultras stage choreographed ‘Go Home’ protest against club’s RedBird owners’. The intro reads: ‘Milan fans staged a remarkable protest against the club’s ownership ahead of their Serie A match against Monza on Saturday.’

Given that The Athletic are owned by the New York Times, we have zero doubts that Cardinale was well aware of the demonstration that took place. Those protests came after the Curva showed up at the 125th anniversary party for a sort of ‘people’s court’, along with many banners at Casa Milan.

Where is Cardinale while all this is going on? The most recent public traces date back to a few days ago, when the news of the acquisition of the historic The Telegraph by RedBird Capital came out. In the news story, Cardinale spoke about the purchase.

Of course it is well known and to a point accepted by Milanista that the Rossoneri are one of many investments that he must devote his time to, but the objection is just how little attention the club seems to be getting.

The last time the owner was at Milanello dates back to August 26. The last time he was in the stands for a match at San Siro was the Venezia game in September, and the last time he saw any game in the flesh – as far as we know – was the Real Madrid Champions League game on November 5.

The hope that Milan fans can cling to is that the management have understood that they have failed, and this clearly has to be a directive from above too. The first move: Igli Tare’s arrival as a sporting director, to fill a crucial gap in the currently ill-functioning Venn diagram of the management.

The coach will be the second step, then the summer window will follow and from there the results tell the story. Because ultimately, in another 1,000 days it is the field we will point to first in determining where Milan stand in the scene of Europe’s elite, whether RedBird are still around or not.