Where do AC Milan go from here?

When Milan beat Napoli in the 2023 Champions League quarterfinals, it felt like further evidence of them returning to relevancy. The majority of the 2010s saw Milan decline to a level not seen in its modern history. Numerous years of inefficient spending created an almost Frankenstein kind of squad. Their financial situation had gotten so bleak that they ended up being kicked out of the Europa League for the 2019-20 season because of breaching financial regulations. Such craziness led to the words “banter era” being synonymous with the Rossoneri during the mid-late 2010s. 

The summer of 2019 was the beginning of something better. Although Milan ended up being removed from Europe, the arrivals of Rafael Leão, Franck Kessié, and Theo Hernández was the start of them piecing together a future title winning squad. Further reinforcements like Mike Maignan and Fikayo Tomori helped complete the puzzle heading into the 2021-22 season. While Juventus were seen as favorites for the Scudetto, Milan had brought in enough high-end talent that a surprise title challenge was in the cards. Under the stewardship of Stefano Pioli, this turned out to materialize. Not only was it impressive for Milan to win the league, but this was done despite having to trim the wage bill by 30%.

2022-23 did see a decline in league performance, with Napoli running away in 1st while Milan finished 4th with just 70 points. However, the Champions League ended up being the saving grace in a manner not predicted in preseason. Successfully qualifying in 2nd place from a group featuring Chelsea, Red Bull Salzburg, and Dinamo Zagreb was massive. What happened afterwards was even greater. As it turned out, their half of the bracket was considerably softer, with the tournament favorites beating each other up on the other side. A long knockout run was there for the taking, and Milan took advantage. Milan did what was needed to defeat Tottenham and Napoli to reach the semifinals, their first since 2007. Although they were clear second best in defeat to rivals Inter, it was a memorable voyage which made up for a lackluster title defense.

The following couple of seasons saw Milan beginning to lose the rope to some extent. There’s the obvious controversial sale of Sandro Tonali, someone who was a key figure at the club. Objectively, Newcastle made an offer which was tough to turn down. That money helped bring in talents like Tijjani Reijnders, Christian Pulisic, and Ruben Loftus-Cheek. However, most within the fanbase have argued the soul of the club has not quite been the same ever since Tonali’s departure. On the pitch, Milan did improve from fourth to second in 2023-24, with a five point increase in their point tally (70 to 75). Despite this, they were 19 points behind Inter and unlike the previous season, were uninspiring in both domestic and European cup competitions. Between that, and growing tactical concerns, this ended up being Pioli’s last season at the helm.

In his place came Paulo Fonseca, who returned to Serie A after a decent two year period with Lille. Milan were aggressive with their spending, signing Youssouf Fofana, Strahinja Pavlović, Álvaro Morata, and Emerson Royal. Royal in particular was met with skepticism, but there was hope for them to improve in the league and reach the CL knockout stage. Instead, various factors led to 2024-25 being the season from hell. Morata did not have the positive impact many had predicted, which led to the signing of Santiago Giménez in the January window to try and stem the tide. Fonseca himself didn’t even make it to the new year, due in part to questionable tactics, ultimately being replaced by Sérgio Conceição. 8th place was their worst finish since 2014-15, and there was no solace to be had from Europe, after getting knocked out by Feyenoord in the knockout phase play-offs. 

This turned the 2025-26 season into a gamble. Milan were hoping to retool the squad considerably, and have it work in their favor to return to the Champions League. Several key figures were sold, such as Reijnders, Hernández, and Malick Thiaw. In came a number of big money transfers with Christopher Nkunku, Ardon Jashari, and Samuele Ricci. Those weren’t without risk, particularly with Nkunku’s injury history and decline in performance with Chelsea. After a decorated tenure with Real Madrid, Luka Modrić signed as a free transfer on a one year deal with an option to extend for a second. Adrien Rabiot returned to Serie A after a sole season with Olympique Marseille. Interestingly, after years of spending more than they sold in the transfer market, Milan had a positive net-spend according to Transfermarkt. 

Milan were also banking that turning back to an old friend in Massimiliano Allegri would be the answer. While hugely successful in Serie A during the 2010s, his return to Juventus for the 2022-23 and 2023-24 seasons was disappointing. The latter of which saw them finish a disastrous 7th place, which saw him let go with two matches left. At this point, most know what you get with an Allegri coached side. Out of possession, a passive structure is utilized to block out the middle. Pressing is not a major part of the defensive gameplan, outside of certain situations. When his teams have the ball, the tempo is very deliberate. In fact, fans have criticized just how slow the sequences can be. There can be a lack of penetrative passing through the middle, instead going from side to side and not risking a live ball turnover in midfield. 

To his and Milan’s credit, the beginning months of the season went quite well. Around a third of the way through the season, there was renewed hope of them contending for the title. 12 matches in, they were in second and only two points back from first. While there were questions over how sustainable Allegri-ball could be over the course of an entire season (particularly with how often they took the lead in matches), the results were solid. Both Leão and Pulisic carried the final third play through the end of 2025 as the forward duo, while Modrić was regularly producing scintillating performances. Their victory over Inter felt like a statement victory, and the possible catalyst for a genuine title challenge.

Things took a turn for the worst once the calendar flipped to 2026. For one, Leão and Pulisic were playing through injuries to keep the team afloat, which impacted their ability to generate goal involvements. Pulisic only had two assists in over 1000 minutes of play in 2026, while Leão was at six goals and assists in over 1200 minutes himself. Nkunku provided output when available, with six goals and assists, but he was in and out of the lineup throughout the second half of the season. There was hope of Jean-Philippe Mateta joining the club in the January window, but worries around his knee eventually led to the deal being nixed. Niclas Füllkrug was brought in on loan, but he wasn’t the solution to their scoring woes. Unsurprisingly, Milan began to fade from the title race as the season approached its conclusion.

By April, Milan’s Scudetto hopes were dashed but they were seemingly on course to cruise into the top four and qualify for CL football next season. Nine points separated them in second from fifth place Juventus, with only eight to play. Even a middling finish would’ve been enough, but instead, Milan’s form cratered and saw them only accumulate seven points. The worries with Allegri’s conservative gameplan throughout the season came to the surface at the worst time possible. They were outplayed for significant stretches, with their best moments tending to be when they had to chase the game from a losing game state. 

Losing to Cagliari in the final match of the season was a microcosm of what went wrong for Milan. They sat back after scoring in the first two minutes, and meekly conceded possession to a Cagliari side which had nothing to play for. Milan had to deal with a barrage of chances against them while being outshot and outchanced, ultimately losing out on the top four.

Overall, it’s hard to make an argument for Milan being unlucky. Their underlying numbers had them as around the 4th or 5th best side in Serie A this past season. According to Statsbomb, they were 4th in non-penalty expected goal difference and 5th from open play only. Both Opta Analyst and Scout Lab had Milan, Roma, and Atalanta at about the same number of expected points in the low 60s. Napoli finishing 2nd with worse underlyings than that trio of clubs is where you can maybe argue variance didn’t go their way, but someone was going to miss out and Milan did not help themselves by letting go of the rope at the end. 

So what happens now? Once it was confirmed that Milan would miss out on CL football next season, there was a massive house cleaning at almost lightning speed. Allegri, CEO Giorgio Furlani, sporting director Igli Tare, and technical director Geoffrey Moncada were let go. Given the manner in which the top four was thrown away, there was likely to be significant consequences.

On the pitch, there could be a massive impact as well. Modrić might end up playing only one season with Milan, which in of itself wouldn’t be shocking given he’s turning 41 in September. However, he still was integral to many of the positive attacking sequences they were able to generate within the constraints of Allegri-ball, so replacing him won’t be easy. Perhaps other key members of the squad would follow suit.

Leão’s future with the club is also up in the air. His ascendancy to stardom was a key reason for why Milan were able to have tangible success a few years ago. However, his goals and assists output in Serie A has steadily declined over the past three years. Some, and perhaps even most of it, could be attributed to outside factors such as tactical constraints and playing through injury this past season. There was also a decline in his creative output, which helped make him so dangerous to begin with. While he has reportedly shown the desire to remain a Milan player, we might have seen the end of him in Italian football.

Milan are in a precarious position. They’ve been in decline over the last two seasons, and if they’re not careful, they could be back in a position not seen since the end of the 2010s. The squad has aged considerably over the years, going from one of the youngest to one of the oldest. There are holes in the squad needing to be addressed, but without CL football, that will be tough to accomplish. Without the funds necessary, they’re also susceptible to a further talent drain. Como’s rise, and Roma’s improvement under Gian Piero Gasperini makes upward mobility in Serie A even harder. It is of utmost importance for them to hire the correct coach who can help them outperform. What happens over the next couple of months may end up determining whether Milan can rescue the rest of the 2020s, or if another dark era is upon the Rossoneri.

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