AC Milan and Massimiliano Allegri are a match made in heaven even if they’re not perfect together

AC Milan and Massimiliano Allegri are a match made in heaven even if they’re not perfect together

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Massimiliano Allegri has won six Scudetti with AC Milan and Juventus

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There are two managers, amongst many others, sitting in free-agency right now enjoying their ‘break’. One has won thirteen trophies, led two different eras of clubs to glory and the other has a grand total of zero trophies. Yet, the moment they’re ready, the latter will have an overflowing inbox.

The former will never have half as what the latter has and who can blame the clubs around the world? Especially after what Mauricio Pochettino did with not just Espanyol or Southampton but what he did with a shoe-string budget at Tottenham. Not even Daniel Levy can believe that Poch actually managed to do what he did as he overreached and hoped that anyone else could replicate that but their current status as a club, tells us just how well that works. But Tottenham’s downfall wasn’t completely Levy’s fault with Pochettino certainly not blameless for the team's drop from glory.

But, the moment he announces that he’s ready to take the reigns at another club, his inbox will be overflowing with offers. Yet, for Massimiliano Allegri, the same simply cannot be said and that’s despite what the Italian has achieved. There have been rumours, however, linking him to some of the biggest jobs in world football but there will always be rumours about anyone. But that has slowly changed especially with some of the world’s biggest sides struggling to cope up with the advent of a new age. It has seen Ligue 1 billionaires PSG consider Allegri with Manchester United and a few others all looking at what could be hopeful moves.

But possibly the most interesting option has to be the repetitive links of a move back to AC Milan. The move certainly sounds funny especially when you put it alongside Allegri’s admittance that he wants his new side to have rules, be disciplined and have a strong internal structure. Make no mistake, even this AC Milan are still footballing royalty. They’re the kings of a world that mortals can only dream of touching with heights that still haven’t been hit. Juventus may have dominated the last ten odd years of the Serie A but the two San Siro sides are the last ones who brought the Champions League back home.

In Italy, the tactics, schemes, they're all bulls---. Football is art and the artists are the world-class players. You don't have to teach them anything, you just admire them.

Massimiliano Allegri

And while Inter Milan may have won the last one by an Italian side, AC Milan are European royalty with only Real Madrid winning more. But not since the heyday, when Silivo Berlusconi’s interests lined up with the club, have Milan actually done something worth noting down with their towering goalkeeper the best thing about the club. That’s Gianluigi Donnarumma and alongside Zlatan Ibrahimovic, who made his return in January, they’ve kept the Serie A giants relevant in this day and age. A time where Milan are cast adrift with their ambition never looking beyond fifth place.

Not since Massimiliano Allegri’s final season with the club have they played or even qualified for Champions League football. Not since Allegri’s final season with the club have they even shown genuine quality beyond Vincenzo Montella’s first season with the club. The list goes on and on but with Ralf Rangnick on his way to the San Siro in the coming months, for once they’re making smart moves. Not just that, for once they’re looking to change what is a paltry future into something more because Rangnick is a class act and a great option for the Rossoneri. But while the German is a great coach, he is a world class Sporting Director.

This is the man after all who made RB Leipzig what RB Leipzig are today, not a bunch of billionaires spending money on players but a club with a youth system, a plan and a pyramid that bigger sides dream of. It’s truly magnificent what Rangnick has created at RB but that is only part of the plan at the San Siro with him coming in as a coach. Yet, that’s where Ivan Gazidis needs to turn the page and figure out, for once, the right solution. That just happens to be Allegri as coach with Rangnick supporting him with whatever the club needs to help the Italian thrive.

However, given the state that the Rossoneri find themselves in, selling that plan will be tougher than anyone ever imagines. But if there is one thing, Gazidis can do it is sell ice to a snowman and this will be worth it in the end. The harder sell will obviously be Allegri especially if the PSG or Manchester United or even Bayern Munich rumours are true. But the Italian has a bone to pick with Juventus and more importantly, with AC Milan themselves which is what Gazidis has to press on. Simply because Allegri’s spell with AC Milan wasn’t good, it was beyond impressive that he managed to achieve what he did with that team including winning their last Serie A title.

He was dealt a terrible hand, Berlusconi and his tax fraud issues, but still somehow managed to keep Milan relevant. Hell, he even managed to beat that 'Barcelona team' with Sully Muntari, Kevin-Prince Boateng, Christian Zapata, Giampaolo Pazzini and a very young Steven El Shaarawy. They would lose the second leg 4-0 to a pissed off Barcelona but for ninety minutes of football and the few days that followed, Milan were the king of Europe again. Till it all came crashing down and their dreams of replacing Allegri with Pep Guardiola went down the drain.

The Rossoneri's faithful need something new to cheer for © AC Milan Media

Nine managers later including Clarence Seedorf, Montella and Marco Giampaolo, AC Milan are exactly where Allegri left them, the same side albeit with a little more financial issues and still no Pep Guardiola in sight. It is why Max Allegri needs to come back to the San Siro and right his wrongs. He has already admitted that “You know in your head that being fired is just part of life as a manager, but it doesn’t stop you from feeling, in your heart, that you failed. When I left Milan, I saw it as a failure of my work.” And for a manager who hates technology with a vested interest, who is about as old-school as a football coach can be and believes in the players more than philosophies, leaving Milan as a failure has hurt him.

But whether or not it hurt Allegri, it has certainly hurt his reputation and his final years at Juventus never helped his cause. Not only that, but his dreams of a balanced squad while building a team with discipline and authority also works perfectly with what Milan need right now. They need stability, they need continuity and more importantly, they need a manager who needs them just as much as they neem him. Neither Montella or Giampaolo could handle the pressure, for Filippo Inzaghi it was far too early and the rest simply failed to live up to anything. Allegri, despite being a serial winner with Juventus, has never been thought of someone deserving to be one of the decades greatest bosses.

Instead, Juventus’ dominance on Italy’s modern stage combined with his lack of success in two Champions League finals and losing to Ajax last season have hurt his reputation. Which is exactly where AC Milan walks into the conversation and leading them back onto their own path of glory will not be easy. Certainly not as easy as Antonio Conte has found it at Inter Milan but, in a hypothetical situation where Allegri takes the job, it would finally give him what he needs. Not validation from the world because that’s something he has never asked for.

But instead, finding the ideal solution at a once great Italian dynasty where he failed to do it the first time. And if in the process he manages to transform not just AC Milan but his reputation and Italian football in the eyes of the beholder, then that’s just an added bonus.

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