As we approach the new year and the midway point of the season, there are still a few gambles that Massimiliano Allegri needs to win.
La Gazzetta dello Sport report that Allegri expects much more from his Milan side in 2025-26, after some restorations like the arrival of Niclas Füllkrug as a centre-forward. Some are obligations, others are gambles, and still others are split between intentions and inevitable paths.
The true objective
In Max’s mind, the objective is clear: finish in the top four. There’s a big difference between fighting for first and fourth, however. The former would yield second-star Scudetto while the latter is the bare minimum required by the owners.
Up until now, Allegri has never openly uttered the word Scudetto. On the contrary, he’s been repeating over and over that Napoli and Inter are the favourites and that the Rossoneri’s true obligation is to return to the Champions League.
The obvious goal is to relieve Milanello of as much pressure as possible by handing it over to the others. The problem is that, at this point, Milan can’t hide: the standings , despite the struggles against lower-ranked opponents, are looking good.
The string of results achieved against their direct rivals is another reason for optimism, even if the disappointing exits from the Coppa Italia and Supercoppa have dampened things. Defensive cohesion must be restored, and signings are needed.

The defence
The cornerstone on which Allegri, as always, builds everything else is the defensive unit. Here too, he’s repeating it endlessly: in the end, in the vast majority of cases, the one who concedes the fewest goals wins, not the one who scores the most.
Compared to last season, Max has rebuilt the defensive line. There’s focus, there’s unity, there’s a change in system that has benefited everyone. The recent hiccups shouldn’t be underestimated: having conceded six goals in the last three games – after the previous six were spread across seven games – is a warning sign.
A few weeks ago, the coach said that to aspire to the title, one needs to concede no more than 25 goals. Given the current state of the league, a higher figure is acceptable, but for now, the Diavolo are already at 13 in 15 games, weighed down by the four goals conceded against Torino and Sassuolo.
With this average, they’d be 32-33 goals at the end of the season, which is too many. Last year Napoli finished with 27, the previous season Inter with 22. The fierce focus of the first three months needs to be restored.
Gimenez enigma
Rehabilitation is needed for Gimenez not only in medical terms, but also in terms of his attacking status. Santi needs to get back to proving to the world that he’s a striker who can score goals. He’ll have to wait until February, when he emerges from a long layoff following ankle surgery.
Allegri has consistently defended the Mexican in recent months, partly because that’s what a coach usually does when one of his players is struggling, and partly because Gimenez has often provided him with obscure but valuable work.
However, being on zero league goals is a burden. Max’s aim? To have the Mexican back ready for the final stretch of the tournament: as the coach always says, everything will be decided from March onwards. Gimenez could be the extra weapon.

Leao’s move
It’s a work in progress, but Max isn’t just an observer on the sidelines: he’s the primary architect of the tactical changes Leao is called upon to make his 3-5-2 work. Drifting out wide isn’t out of the question, but there has to be more consistent end product.
The Portuguese is learning, he’s applying himself, even if it remains a complex transition. This is one of Allegri’s biggest gambles: when and if he pulls it off, the upgrade for the Rossoneri will be enormous. The goal isn’t out of reach: Leao has already scored a few goals like a true striker.
Midfield goals
Recently, Allegri has already publicly stated that he expects the midfielders to contribute more in front of goal. Some have come since but it’s still not enough. So far, no one has gone beyond a single goal: Modric, Rabiot , Loftus-Cheek, Fofana and Ricci are all on one goal.
Considering that Allegri’s style of play calls for the midfielders to contribute significantly to the attack, the haul is meagre. In August, the Rossoneri coach said: “Loftus-Cheek and Fofana must score at least 15 goals between them; it’s a target I’ve set and one I’m committed to.” So, a lot of work is needed.

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