Plan and Execution
On June 6, 2023, AC Milan officially announced that sporting director Paolo Maldini would be leaving the club with immediate effect. A statement was published on the club’s official website, but the decision was never acknowledged on social media. The statement didn’t quite come as a shock, because as always the media tells us about these developments before they become official, and this is actually the only reason we know that Maldini’s partner in crime at the club, Ricky Massara, would also be leaving the club. With the two having largely functioned as a duo at the club, it was presumed that both Maldini and Massara would be relieved of their duties, although the headlines pertained to Maldini leaving since he had the bigger role and was the bigger name. However, there have since been reports that Massara decided to resign upon finding out about the dismissal of his partner. In any case, Milan never officially acknowledged Massara’s departure. The decision as well as its aftermath made for one of the most controversial moments in the history of the club. The supporters were generally outraged, not only because the decision was dubious from a sporting perspective—in fact it was likely not even primarily because of this. Rather, the outrage was provoked by the optics of the decision. Together, Maldini and Massara had played an integral role in improving Milan’s financial situation from disastrous and debt-riddled to the best in Italian football, all while the results on the pitch improved considerably—first being highlighted by the club’s return to the Champions League for the first time in eight years in 2021, and then culminating in the club’s first scudetto in 11 years the following year. Letting go of Paolo Maldini was particularly problematic, because he was not only a hero to the club as an administrator, but, of course, he also remains the club’s undisputed greatest player of all time. His father was a club legend, he, himself, was born and raised in Milan, and he played for Milan from his childhood to the age of nearly 41. On that note, another problematic aspect of the decision in question was how it was communicated. Again, Massara’s departure was never even officially acknowledged by the club, and Maldini’s departure was officially announced with a brief, formal statement that showed very little respect for his work at the club in previous years. More importantly, it showed a lack of respect towards the greatest Milanista of all time. Furthermore, it bears repeating that the decision was never mentioned on social media. A year in retrospect, it is also notable how Stefano Pioli’s recent departure was communicated in contrast. The club statement was shared on multiple social media platforms, and the club statement was remarkably more detailed and emotionally charged; compare “AC Milan extends heartfelt thanks to Stefano Pioli and his entire staff for leading the First Team over the past five years, securing an unforgettable League title and re-establishing AC Milan’s consistent presence in the top European competition. Stefano’s professionalism and human touch have significantly contributed to the growth of the squad, embodying the Club’s core values from day one”, to “We thank [Maldini] for his years of service in the role, contributing to the return to the Champions League and to winning the Scudetto in 2021/22.” Additionally, a video paying tribute to Pioli was made by the club, which obviously wasn’t the case for Maldini. Now, consider that Stefano Pioli’s departure from Milan was widely demanded by the supporters, whereas Maldini’s departure not only came as a shock, but was also considerably more emotionally sensitive considering he is the undisputed greatest legend in the history of the club. The communication of the Maldini-saga certainly doesn’t hide how the club– or rather Gerry Cardinale, felt about him. Meanwhile, another issue with the communication was the lack of an explanation of the decision.
The reason why Maldini (and I suppose also Massara in practice) was dismissed, remains unknown. Naturally, with today’s climate of football journalism, countless reports aiming to explain the decision as well as where Milan were heading came out following the decision; the supporters were given a million different answer to the same question, and thus they learned nothing. It’s been over a year since it all transpired, and we still don’t know exactly what happened. The widely presumed theory is that Gerry Cardinale, who became president of the club along with its change of ownership in 2022, wanted to do what any new president/owner of a football club tends to want to do; establish a new regime of their own choice. Following the scudetto, this wouldn’t have been possible in 2022—although it almost did happen, as Massara and Maldini’s respective contracts were both expiring in the following summer; contract extensions were difficult for the club to pull off amidst the ongoing change of ownership, but the club was quite literally able to do it in the last minute in the end. But, in 2023, letting go of the duo would have been more achievable, and it is assumed that this is how it all developed: Gerry Cardinale wanted a new sporting direction of his own choice when he arrived at the club, and since he couldn’t do it in 2022, he had to do it in 2023 instead. It wasn’t anything personal; he just wanted his own guys working for him. Still, this doesn’t explain why Maldini was fired, whereas Massara presumably would have stayed if not for his own decision to leave. It also doesn’t explain why Giorgio Furlani remained at the club as CEO and seemingly got a bigger role in the club’s sporting department—in the club statement about Maldini’s departure, it says that “[Maldini’s] day-to-day duties be performed by a team working in close integration with the first team manager, ultimately reporting to the CEO.” Almost exclusively thanks to the media, we now know that the team in question consisted of Geoffrey Moncada and Antonio D’Ottavio, with Zlatan Ibrahimović having since been added to that team. What’s notable about that group is that the former two were reportedly internal hires—although we do not know for sure in regards to D’Ottavio, because he is not mentioned on the club’s website and he also doesn’t have a Transfermarkt profile—while Zlatan Ibrahimović had obviously played for the club as recently as just a few months prior.
So, although it is assumed that Gerry Cardinale had already decided he wanted to change Milan’s sporting direction as soon as he arrived at the club, this doesn’t seem to be the case for a number of reasons. First of all, the new management practically exclusively consists of people who were already working at the club when Maldini was fired. Of course, it is also remarkable that Ricky Massara was never actually fired, but rather left on his own accord following the dismissal of his partner. In fact, the biggest sign that the Maldini-saga wasn’t premeditated—so to speak—is the fact that it occurred so suddenly, and here it might be appropriate to go back to how Stefano Pioli’s dismissal was handled. The media largely claimed that Milan had already decided to let go of Pioli at the end of the season by December, which is why that decision was announced prior to Pioli’s final game as Milan head coach—so that he could be honored and thanked by the management, the players and the supporters at the San Siro. As for Maldini, there had been some speculation that he could leave at the end of the season during Spring of 2023, but it wasn’t until shortly after the season that it was reported by reliable sources that Maldini’s dismissal was a real possibility. This didn’t come from out of nowhere either, but from a series of meetings between Cardinale and Maldini following the end of the season. But why does all of this matter? Well, I think we’re really getting to the essence of why the Cardinale–Milan project won’t work out. By all means, we can analyze the sporting decisions and how they impact the club; how alternative decisions could (have) impact(ed) the club—I certainly have, and on this end I am extremely negative (read this and this). However, at the end of the day the biggest sign that the Cardinale–Milan project won’t work out is that it’s all a facade.
Plan.
There is a story that Gerry Cardinale wants you to believe, and I will tell it the way I see it. He wants you to believe that Paolo Maldini and Ricky Massara left the club because Gerry Cardinale 1) ideally wanted his own sporting regime, and 2) had a specific criteria for how his sporting regime would operate; a criteria which Maldini definitely didn’t fit, and perhaps not Massara either. He wants you to believe that he has a Plan, and we were quickly introduced to this Plan following Maldini and Massara’s respective departures. As Cardinale has reiterated, Milan are at a financial disadvantage compared to the Premier League, above all, and he wants to combat this issue with financial sustainability, as well as other strategies that should help bridge the gap with the Premier League; a new stadium, marketing, etc. The club wants to achieve financial sustainability through a buy-to-sell strategy; through intricate scouting of young players, Milan can bring in talents who will grow at the club, be sold for more than they were bought, with the money subsequently being reinvested to create a cycle—increasing the value of the squad and thereby also the club in the long-term. Geoffrey Moncada will be the mastermind behind this strategy—Milan’s former head scout excels at finding excellent-value talents, having reportedly identified the likes of Rafael Leão, Pierre Kalulu, Mike Maignan, Hugo Cuenca, Tiago Djaló, Sven Botman, Enzo Fernández, Randal Kolo Muani, Mohamed Simakan, Manu Koné, Julian Álvarez, Moisés Caicedo, and Dominik Szoboszlai in the past. The Plan clearly draws inspiration from a club like Dortmund, which has excelled at youth development and financial stability for years, and has found relative success with significantly less resources than Milan. Ideally, Cardinale’s Plan is to make Milan a higher-scaled version of Dortmund; thereby achieving more material success with essentially the same model. Initially, it was the media that presented Cardinale’s post-Maldini Plan as also being heavily inspired by Moneyball; overcoming financial restraints with the help of intricate scouting and data-driven recruitment, thereby identifying the top talents that the richer clubs have overlooked. Since then, this inspiration has become more explicit, with Cardinale having spoken about it, himself; Cardinale and Billy Beane, the father of Moneyball, know each other, and the latter has been an integral source of inspiration for Cardinale’s project at Milan. There you have it—that is the Plan, and you can say what you want about whether or not Milan are better off without Maldini; you can say what you want about how his dismissal was handled, but this Plan doesn’t sound too bad. Except it’s not about the Plan. It’s about the Execution.
Execution.
After being promoted to technical director of the club, Geoffrey Moncada was set to play perhaps the biggest administrative role in executing Milan’s new Moneyball-inspired Plan. And in fairness, there were reasons to believe that he was better suited for this role than Paolo Maldini, given his experience with scouting and his track record in terms of the results of his scouting—as previously alluded to. Argentina and the smaller countries in South America, as well as France (above all), looked like the primary markets that Moncada was set to explore, and it was exciting to imagine which overlooked talents he would be able to identify. However, for as much as people complain about Milan going for obscure, young players rather than experienced and proven players who can make a short-term impact, these complaints are wildly out of touch with reality. Not only has Milan’s recruitment remarkably not been particularly youth-centered since their sporting revolution, they have also only signed one player from Moncada’s areas of expertise. It really is hard to explain. One explanation could have been that there are some logistical issues to signing players from South America, given the squad registration rules in the Serie A and the substantial adaptation that such a transfer demands from the player—from the social side to the football side. Well, funnily enough, the one signing from Moncada’s areas of expertise that was made was Marco Pellegrino, from Argentinian club Atlético Platense. To this day, this remains perhaps the only signing Milan have made that completely corresponds with its supposed Moneyball-inspired vision. And the results? Well, we’ll get there. For now, let’s continue to establish that Milan’s recruitment over the last year actually hasn’t been very youth-focused and Moneyball-inspired at all. Again, people love to complain about Milan signing obscure young players, and those people are simply delusional. So far in this new era, Milan have made 11 signings. How many of those players do you think were u23—that is to say, not even necessarily particularly young, but at least somewhat young? The answer is five. That’s right, Milan’s new, highly youth-focused project has seen them sign less “young” players (if you want to use u23 as the threshold), than players who are not “young”. In fact, three of those five u23 players—Marco Pellegrino, Luka Romero and Filippo Terracciano—have combined for a total of just 4.0 90s in all competitions for Milan so far, and if I told you just how poorly received those minutes were, and you didn’t know any better, you wouldn’t believe me. As for the other two u23 signings—Noah Okafor (23 when signed) and Yunus Musah (20 when signed)—the one whose role has most resembled that of a starting player so far is Musah, and he ranked 10th in minutes played last season, whereas Okafor ranked 19th (via FBref). In the end, there were only really three new signings that ended up having a significant role in the first team last season; Tijjani Reijnders (26 next week), Ruben Loftus-Cheek (28), and Christian Pulisic (26 in September). Oh, and did I mention that Geoffrey Moncada, who is supposed to be the leading figure of Milan’s recruitment departure, didn’t sign a single player from France last summer—despite being from France; despite having previously worked as a scout in France; despite the fact that we know that he loves the French market for reasons that align with Milan’s supposed Plan? 2023 surely wasn’t the summer that was anticipated, but maybe this was just a glimpse of what the new Milan project entailed? Maybe the Moneyball aspect of the project didn’t necessarily just mean intricate scouting and focus on young players, but also taking advantage of market opportunities; signing talented players who were undervalued? Well, it seems like this is almost all Milan did, but sure, signing Ruben Loftus-Cheek, a former Chelsea wonderkid, on a “bargain” deal; Christian Pulisic, another former wonderkid, on another “bargain” deal; Tijjani Reijnders, one of the most statistically outstanding midfielders in the Eredivisie, on a “bargain” deal, was not completely antithetical to the Moneyball– and financial sustainability aspects that supposedly defined Milan’s new project. But really, is this particular strategy a part of this new vision, or does it define the vision? Because if we look at a lot of the players Milan have been linked with so far this summer, it’s comically difficult to notice a difference.
By all means, it is still early doors, but whether it’s in reference to fringe links or confirmed targets of Milan, nothing seems to have changed in terms of Milan’s strategy, this summer. In terms of fringe links, you have the likes of Adrien Rabiot (29), Pierre-Emile Højbjerg (29 in August), Memphis Depay (30), Artem Dovbyk (27), Santiago Giménez (23), Jonathan David (24), Serhou Guirassy (28), Ermedin Demirović (26), Romelu Lukaku (31), Matty Cash (27 in August), Youssouf Fofana (25), Emerson Palmieri (30), Diogo Leite (25), Mats Hummels (36 in December), Douglas Luiz (26), Maxence Lacroix (24), and Alessandro Buongiorno (25). Keep in mind, these links all come from relatively reliable sources at the very least. Furthermore, as for the more confirmed links, you have Joshua Zirkzee, Emerson Royal, and Tiago Santos. The one player here who strongly fits Milan’s supposed vision is Tiago Santos, who is 21 years old and plays for Lille in France (!)… the only problem is that it seems like Emerson Royal is the preferred option between the two. He, in contrast, is a 25-year old who was somewhat highly rated when he was… owned by both Real Betis and Barcelona? Don’t ask me to explain how that worked—the point is that Emerson was never exceptional in Spain, and then he indisputably flopped at Tottenham, which is why they now want to sell him. So, again, what is this? A market opportunity, which does align with the club’s presumed philosophy to an extent, but when the club’s recruitment is almost entirely centered around market opportunities, you have to ask questions. Because identifying undervalued players who used to be really good should only be an alternative strategy to identifying players who stand out from a data standpoint and/or are very young, with high potential—if the goal is to bring in players who can increase in value, what do you think is the easiest way to do that, generally speaking? Of course, it is to focus on young players, because they tend to have the most growth to do, and with growth of ability comes growth of value. Alternatively—or even simultaneously—the data aspect also comes in here; players who are seemingly way undervalued financially compared to their data can show their true value in a different environment, and thereby rise in value; that’s essentially the gist of Moneyball. Really, the latter example is more reminiscent of signings such as Ruben Loftus-Cheek, Christian Pulisic and Emerson Royal, but I think the resemblance is quite vague. First of all, this strategy is obviously applicable to players of all ages, whereas we see a clear trend of 23+ year olds when it comes to the players who fit into the “market opportunity” criteria. More importantly, though, these signings cannot possibly fit the Moneyball criteria, because the players in question really aren’t that eye-catching from a data standpoint, nor are the values of the respective signings particularly great. If you look at Ruben Loftus-Cheek, for example, Chelsea had no leverage whatsoever, as he had a year left on his contract, was a slightly older player in a squad full of extremely young players, was one of countless midfielders at the club (clearly one of the odd ones out at that), and he was yet to really ever prove himself to be a particularly great player at the senior level—at least to the general public. Furthermore, Loftus-Cheek was fantastic from a data standpoint in 2021–22, but in 2022–23, the season before Milan signed him, he had clearly regressed and didn’t really stand out in any relevant non-buildup metrics. In fact, on top of all of that, he was also notoriously injury-prone. Despite all of this, Milan were ultimately forced to pay a €20m transfer fee (bonuses included) for Loftus-Cheek. As for Pulisic, it is essentially the same story; he was a terrible asset for Chelsea for the same reasons Loftus-Cheek was, and Chelsea had no leverage in their negotiation with Milan. Moreover, Pulisic had been quite underwhelming–poor from a data standpoint for multiple seasons when they signed him, yet Milan ultimately paid a €22m fee (bonuses included again) for him. As for Emerson Royal, his contract expires in two years, it’s very obvious that Tottenham don’t want to keep him, and he also doesn’t stand out from a data standpoint, yet Milan are confirmed to be interested, and it is looking likely that they will pay a fee in the region of €20m to land him. It’s hard to argue that such signings completely align with the philosophy that we were promised about a year ago. In fact, even Joshua Zirkzee does not stand out as any sort of Moneyball signing at all. He has a €40m release clause, at 23 years old he’s not *particularly* young, and he’s the reigning Serie A Young Player of the Season. Maybe the last detail implies that Zirkzee is really good, but that’s really not the point here. The point is that Zirkzee is yet another potential signing who doesn’t really fit Milan’s supposed Moneyball philosophy; he would be Milan’s third most expensive signing ever in terms of transfer fee, and in terms of wages, commissions and transfer fee combined, he would perhaps become Milan’s most expensive signing ever, which is not to mention that the data only really speaks against his favor.
Looking at how Milan operates on the transfer market makes it clear enough that the Moneyball project is a facade, but it really doesn’t end there. I think what Milan did in June last year is the icing on the cake. Again, Paolo Maldini’s dismissal remains a bit of a mystery, and it really doesn’t seem like it was caused by Gerry Cardinale simply wanting to work with staff that he had hired. What we almost certainly know is that there was a disagreement between between Cardinale and Maldini leading up to the latter’s departure, but the details remain unknown. Did they disagree on a strategical level? First of all, that would make the very cold and insensitive communication of Maldini’s departure odd. Perhaps more importantly, though, we really haven’t seen a radical change in sporting strategy since the departure of Maldini. One of the things that surprised me so much about Maldini’s dismissal—a decision which was allegedly in favor of a more youth-centered and data-driven project—was the fact that Maldini and Massara excelled in identifying talents. For instance, in retrospect I think we can recognize that Charles De Ketelaere was not an example of poor talent identification from Maldini and Massara, and in the same summer he arrived, Maldini and Massara also brought in a then-21-year old Malick Thiaw for a bargain fee of just €7m. Thiaw has since developed into a starter, and has impressed enough to attract interest from the likes of Real Madrid and Bayern München. Bear in mind, this was from a perceived bad summer from Maldini and Massara. In previous transfer windows, the two had signed the likes of Theo Hernández, Ismaël Bennacer, Rafael Leão, Fikayo Tomori, Pierre Kalulu, Sandro Tonali and Mike Maignan. Moreover, Ruben Loftus-Cheek had already been strongly linked to Milan by the time Maldini was fired, implying that he was a target of Maldini and Massara’s, yet Milan ended up signing him after the departures of Maldini and Massara anyway. The same can almost be said about Daichi Kamada, who almost looked like a done deal before Maldini’s dismissal, yet who Milan continued to pursue following Maldini and Massara’s respective departures, only to drop their interest in him once they decided to transition from a 4–2–3–1 to a 4–3–3… in the middle of the transfer window. So, was there really ever a disagreement in sporting strategy between Maldini and Cardinale? I could somewhat understand the possibility that Milan moved on from Maldini in order to establish an even more radically youth-centered and data-driven project—for instance Maldini has mentioned how the scouting department, among others, were against the club signing Sandro Tonali in 2020, likely because his data wasn’t amazing. However, if anything, Milan’s post-Maldini recruitment has just been increasingly redundant and looks less influenced by data analysis and focus on youth than Maldini and Massara’s recruitment did.
So, Maldini’s mysterious dismissal was one bizarre thing that happened last June, and speaks against the existence of a new Moneyball-inspired project if you really look into it. However, something even more egregious would transpire the same month; Cardinale was set to decide the future of then-head coach Stefano Pioli, and what did he do? He confirmed him as Milan’s head coach heading into the 2023–24 season. I’ve already dedicated millions of words to criticizing Stefano Pioli, but I have to emphasize how little sense this decision makes. In fact I have already made this point a million times, but I have to make it again: Firing Paolo Maldini and confirming Stefano Pioli is one of the most disgustingly unjustifiable sporting mistakes I have ever witnessed. What was the purpose of Paolo Maldini’s dismissal? As established, we really don’t know. We haven’t seen a radical change of sporting strategy since he was fired—it has just gotten worse and more redundant. The issue clearly also wasn’t that Cardinale wanted a handpicked management, because Ricky Massara was ultimately never fired, and the hires that followed his and Maldini’s respective departures were all internal. There was no sense in firing Maldini, and there still isn’t, but let’s assume this isn’t the case and that Milan really did undergo a sporting revolution that saw them focus more heavily on youth development and data-driven analysis last summer—in that case, in what solar system does it make sense to keep Stefano Pioli? Last summer I repeatedly said that it didn’t really matter who Milan would sign, because none of the players would develop under Stefano Pioli anyway. That’s a pretty hard stance to take, which you can only reasonably do with a lot of evidence to back it up, and while it was just a hypothesis at the time, it ended up being completely true in the end. Stefano Pioli is not merely an unideal coach for youth development, he is an active liability. For instance, in Maldini and Massara’s final season at the club, we saw Pioli destroy one of Milan’s most expensive signings ever, in Charles De Ketelaere. Again, the narrative of Pioli having ruined De Ketelaere began as a hypothetical, but it has since been all but confirmed. From his coaching in training, to his designation of roles, to his tactics, to his integration of new signings, to his handling of playing time, to the constant injury issues which have persisted for years, Stefano Pioli is a monumental liability to any club that wants to develop players. If you are serious about player development; youth development, and you aren’t afraid to make bold decisions, what could possibly compel you to actively decide to retain such a manager? I will give Cardinale an ounce of credit and say that one quite substantial decision has aligned with the Plan; the appointment of Paulo Fonseca as head coach, following the eventual dismissal of Stefano Pioli—perhaps the latter decision deserves some credit/acknowledgement as well. Sure enough, there are some question marks about Fonseca’s ability as a coach, but what he can do is develop players; at Lille he has not only integrated players from the academy and helped other young players take significant leaps—he has also completely transformed a lot of older players. The only issue here is that if Cardinale and his team recognize these qualities now, how could they not last year? Fonseca’s 2022–23 season was by almost all metrics a more impressive campaign than his 2023–24 season, and more importantly he was available for Milan to hire in 2023—he still had a year left on his contract, but multiple sources reported that he came close to leaving Lille in order to take on the Marseille job, which he obviously could have done with Milan if they had been interested. But, as far as we know, they weren’t. They stuck with Stefano Pioli instead, which is why Milan’s youth-centered Moneyball project has not just seen them make a shocking lack of young signings, but has also seen the team achieve more regression than growth.
With all of this having been established, one question remains, however: Why? Why is the contrast between Gerry Cardinale’s Plan and its Execution as disastrously stark as in the TV episode the title of this article is referencing? Although he has partly done so indirectly, Cardinale has promised Milan a project centered around intricate scouting and data analysis, as well as a focus on youth development—following an enormously controversial sporting revolution at that—and yet he hasn’t followed up on this whatsoever. Why? Was he lying all along? What would he gain through such a lie? Well, originally the title of this article wasn’t meant to be a reference, but it fits particularly well given that there are more than a few parallels. One such parallel gives us about as good of an answer as you’ll find to the question(s) above. Largely due to the club’s lack of sufficient communication since the arrival of Cardinale, we don’t know what he thinks nor what his intentions are, but at the end of the day I’m not too cynical towards him in the latter regard. My answer to the ultimate question is that I just think he’s out of his depth. He’s not meant to work in football, just like Jimmy McGill isn’t meant to be a lawyer; Gerry Cardinale has no actual qualifications to work in football, and Jimmy McGill dubiously got his law degree through the University of American Samoa. Cardinale exposes perhaps the ultimate issue with the power structure in Italian football, which is the undemocratic ownerships of its clubs. Italian football fans are by in large still football romanticists; a football club is not a sports organization or a corporation, but a sociocultural symbol; it represents a city or region, its people and its culture. This means that the people are the true representatives of the club, rather than its executives or players; the club belongs to them, and their love for it is unconditional. This applies to plenty of countries, but especially to Italy given the relationship it has with football. Despite that, this is not how it works in practice; in Italy, the football clubs may belong to the supporters, but they are owned privately. Thus, private interests, which are not uncommonly at odds with those of the supporters, are the interests that are adhered to. This power structure is what leads to a bit of a paradox in terms of the “unconditional love” of the supporters; they don’t struggle to support their club through thick and thin, but given their lack of democratic power over their club, they are forced into collective action that quite literally sees them stop their support for the club, if they want to bring change. Milan are a textbook example of this, as their main supporter group, Curva Sud Milano, decided to protest the club’s management by quite literally choosing not to support the club at the end of last season; either through not showing up to the matches whatsoever, or by remaining in silence when in attendance of the matches. Now, what do the people actually think of Gerry Cardinale, the most powerful figure at their football club? Well, generally speaking, they hate him, and they don’t want him to have anything to do with their club. Are they right to do so? Well, they may very well know just as little about football as Cardinale, but at least they have the ethical right to impact Milan; Milan belongs to Milanisti, and Milanisti only. Alas, that’s not how it works in practice. In practice, Milanisti are powerless; helpless; they have suddenly found themselves in quite the jam, and they cannot get out of it.
