
How Leao Will Get More Freedom Under Allegri?
Allegri plans to take a different route because he knows that the talented Almada native isn’t a Di Livio-type soldier who relentlessly tracks back and forth down the flank. This is where Allegri’s experience with Cristiano comes in handy. Back in 2018-19, Juventus often lined up in a 4-3-3, the same system Milan is likely to use. Just like Ronaldo, who operated wide left and needed cover when possession was lost, Leao will benefit from a similar support mechanism.
At Juventus, Matuidi was the player who drifted to the left flank, turning the formation into a 4-4-2 when defending, while Dybala or Bernardeschi dropped into midfield. At Milan, this job will often fall to Pulisic, who frequently performed that role last season. The question is: who will shift left to cover Rafa’s back? It’s hard to expect Modric to do it regularly at this stage of his career. The responsibility could land on Fofana or Loftus-Cheek, though the final midfield setup depends on whether Milan completes the deal for Jashari.
One certainty is that Leao will be asked to contribute more defensively than Ronaldo did when he first arrived in Serie A, simply because Rafa is younger and holds a different status. Still, Allegri will be careful not to exhaust or stifle him, convinced that the No.10 has yet to display his full attacking potential. That’s why Rafa will start his runs closer to the opposition penalty area.
The Left Back Question
Another crucial piece of this puzzle is the new left-back Milan plans to sign. Unlike Theo Hernandez, who was brilliant in attack for five years but increasingly unreliable defensively last season, the new fullback must be more diligent with defensive cover and better at closing down space. With extra protection from the left-back and midfield, the hope is that Leao will finally showcase the best version of himself. Conceiçao tried to unlock him with a 3-4-3, while Allegri will rely on his signature “lopsided midfield.”


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