Cassano drew a stark comparison between Allegri and Mourinho, arguing that both coaches have become relics of another era. He lamented what he views as a betrayal of Milan’s traditional values, which are attacking flair, elegance, and expressive football. In his eyes, the current iteration of Allegri’s Milan stands in direct conflict with those ideals.
Speaking on the Viva El Football podcast, Cassano issued a blistering assessment of Milan’s approach, suggesting the club’s identity is being eroded under Allegri’s watch.
“Remember what I said about Mourinho being finished and that sooner or later he would end up being forgotten. The same will happen to Allegri,” he said.
“I can’t imagine Milan in 2025 playing dreadful football because of their coach: Milan are history, beauty, aesthetics and quality. And what do they do? Everyone sits in front of the goalkeeper; there’s no depth, then you win the ball back, counter-attack and score.”
For all the criticism, Milan’s numbers are strong. They have scored 19 goals and conceded just nine in their 13 Serie A fixtures. The team boasts of a defensive solidity characteristic of Allegri’s coaching style. But Cassano contends that results alone should not shield the manager from scrutiny, especially at a club built on decades of artistic football.
Cassano’s comparison to Mourinho arrives at a time when the Portuguese manager’s recent struggles remain fresh. Mourinho left Fenerbahce earlier this year following a difficult stint lasting just 62 games,as he was dismissed after a Champions League play-off defeat to Benfica. The former Chelsea and Inter boss, who has two Champions League titles to his name, endured a testing time in Turkey was fraught with frustration, particularly with officiating, and he openly admitted upon returning to Portugal that he had chosen the wrong project.
“My career so far has been rich; I’ve coached the biggest clubs in the world, in different countries,” he said after taking the reins at Benfica for a second time. “I made the wrong choice; sometimes I don’t have the right word in Portuguese… no regrets, because regrets don’t help us at all in life, but the awareness of what we did well and what we did wrong exists. I made a mistake going to Fenerbahce; it wasn’t my cultural level, it wasn’t my football level, it wasn’t my level. Obviously, I gave everything until the last day.”
Former Fenerbahce president Ali Koc later shed more light on the separation, describing it as “painful” while insisting the club needed a more expansive style to suit the Turkish side’s expectations.
He said: “Why did we let go of Mourinho? I’m explaining it here for the first time. It was a bitter parting. Our chemistry was perfect, and his accomplishments are evident. Just being able to bring him here was a great achievement. Above all, it was difficult to part with someone I was friends with. We knew our coach was a defensive player when we brought him in. But we talked about the need to play more dominantly at the end of the season. Earning 99 goals and 99 points is our genetic code.
“Being eliminated by Benfica wasn’t a problem, but the way we were eliminated was unacceptable. This made me feel like last year’s football would continue. We parted ways because we believed this squad would play better football at this point. This kind of football works in Europe, but in Turkey, we have to crush them in most matches. We’re struggling to get ahead after falling behind in every match.”
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Cassano himself won the only Serie A title of his career under the same man he now savages. His 2010-11 Scudetto triumph came with Allegri at the Milan helm, yet that shared success did little to soften his message. Mourinho, meanwhile, appears to be steadying himself at Benfica. After a shaky start back in Lisbon, his side have climbed to third place in the Liga Portugal, six points adrift of Porto, and now look far more competitive heading into their clash with Sporting on Friday evening.
For all the condemnation, Allegri’s Milan team remain firmly in the Serie A title race and are defensively robust. Hence, the Italian manager might just stick to his guns, ignoring Cassano’s criticism as noise. The Rossoneri resume their campaign on Thursday with a Coppa Italia Round of 16 trip to Lazio.
