Ambition, timing and risk: Why Milan and De Zerbi might be a perfect marraige

By Christian Montegan -

Attempting to pinpoint the exact reasons why Milan have suddenly faltered dramatically since the glory days is nearly impossible considering the multiple elements behind the decline. One argument to support the demise involves decision-making and the manager personnel appointed.

Carlo Ancelotti, undisputedly one of the greatest tacticians of all time who claimed two Champions League titles and a Scudetto during his time at the Rossoneri, became a proven coach with a raw ability to keep fans on the edge of their seats and eagerly anticipated the next matchday around the corner.

Since 2009, 11 managers have come and gone whether they were interim caretakers or seen as the right man to lead the club toward the foreseeable future.

From those names, you can argue that Massimiliano Allegri is the most polished and capable personality that the club has hired – touted at the time as the next big thing in Italian football after his spell at Cagliari, helping Milan claim their 18th Serie A title.

A star-studded crop of world-class talent in the form of Zlatan Ibrahimović, Alexandre Pato, Andrea Pirlo, Kevin Price-Boateng, and Alessandro Nesta to name a few might have propelled that piece of silverware, yet the football displayed wasn’t always pleasing on the eye and had supporters craving for more in a weird sense.

Gennaro Gattuso, Filippo Inzaghi, and Clarence Seedorf did their reputation no favours by accepting a gigantic and implausible task of turning around a historic club with minimal coaching experience and pedigree, whilst the late Siniša Mihajlović did implement ‘grinta’ and rediscovered pride for the badge, there was no clear identity on the pitch from a footballing perspective.

Amidst the ongoing search for a new manager to replace the outgoing Stefano Pioli, a lingering candidate has entered the frame from a pipedream to a real possibility: Roberto De Zerbi.

Shock news broke before Brighton and Hove Albion’s final fixture of the season that the Italian would be stepping away from managerial duties, reportedly due to sharing different ideas with owner Tony Bloom.

De Zerbi’s name has vaguely emerged over the past couple of weeks, though the main hurdle that halted Gerry Cardinale and the board from progressing with the idea was the reported €15m release clause on the ex-Sassuolo boss’ contract to make the jump.

As expected, now that the release clause is out of the equation, rumours of the 44-year-old reuniting with the seven-time European champions have exponentially accelerated.

Having previously developed in the Milan youth academy, De Zerbi confessed his love for the club in an interview with La Gazzetta dello Sport.

“I grew up at Milan, I lived three years at Milanello and my football education comes from Milan, the real one, my football education comes from the Milan of Baresi, Tassotti, Maldini, Boban, Savicevic, and of Costacurta,” De Zerbi admitted.

Despite the opportunity opening up to alter plans, current Lille manager Paulo Fonseca is still currently leading the charge to secure the top honour per multiple reports.

The former Roma boss has performed above expectations at the Italian capital and now Ligue 1 where he has experienced under-resourcing and a limited environment to thrive – unable to maximise his full potential.

At some point, honesty must prevail. Are the top European clubs lining up in pursuit of Fonseca? The answer is no. Instead, De Zerbi has been linked with the world’s top clubs, so wouldn’t it make sense to do everything in Milan’s power to secure his services and compete with the elite down the line?

As we witnessed with the Julen Lopetegui saga, plans must be reassessed when even the slightest opening presents itself like De Zerbi. This scenario makes more sense to change direction in comparison to the imminent Lopetegui signing.

When results and performances don’t live up to the billing, the manager’s head will naturally be the first in the firing line. At the same time, the personality of a coach can go a long way toward connecting with the fanbase and providing a glimmer of hope and excitement – just as was the case with Ancelotti all those years ago.

De Zerbi is changing football and the feeling is that the ball is in Milan’s court to push as hard as possible to build a long-term project. His popular attacking philosophy envisions what the modern game is all about; possession-based style, high pressing, high intensity, quick passing, and constant movement.

It feels too good to be true because Milan often never makes it easy on themselves, mainly due to being reactive rather than proactive.

What would opting for Fonseca ahead of De Zerbi say about the ambition at Milanello? What message will it send from the ownership being equipped to handle these big decisions?

Then there’s the other side of the token with the risks attached to De Zerbi’s attacking mentality, an element that must be taken into serious consideration.

Still yet to find the balance on the defensive side of the ball, his Brighton outfit conceded an average of 1.57 goals in the Premier League since October 2022 and were knocked out by Roma 4-1 on aggregate in the Europa League round of 16 after clearly suffering from a lack of energy caused by the demands of his tactical style.

It draws similar comparisons to the legendary Arrigo Sacchi who revolutionised the game in his own right, going as far as abolishing the defensive sweeper role and adopting a back four with a high line. What may have been viewed as an attacking method of madness, was soon hailed as genius work to transform Milan into an attacking machine.

Let’s not forget that De Zerbi hasn’t won anything tangible aside from a single Ukrainian Super Cup during his time at Shakhtar Donetsk. Do the fans prefer guaranteed entertainment or is winning trophies more important?

Better yet, perhaps De Zerbi’s forward-thinking can evolve into a Sacchi-like era that can achieve the best of both worlds – albeit with the backing of the club and some patience.

After the defeat to Manchester United two days ago, the Brescia-born manager touched on his tireless study regime and willingness to always adapt.

“For sure, if I have to stay at home (for) three, four, five months, it should be not a problem because I will work,” De Zerbi said.

“I will work studying different games, different teams, the style of different coaches. Football is in development. Every year it is different and you have to keep the level if you want to stay at the top.”

At a time when Milan has been forced to settle for fringe players in the Premier League over the years, surely this is the chance to poach one of the most knowledgeable and exciting young coaches in world football – who isn’t on the fringes.

If not, then it would feel nothing other than a wasted opportunity.

Tags AC Milan Roberto De Zerbi


  1. DeZerbi will not be our next coach because he just became available and Milan already have their coach picked.

    1. Lol nothing is signed, if they want they can go for De Zerbi. But it seems he is a very ambitious coach and thats probobly what Milan management doesn’t want.

    2. De Zerbi is the man and there is no other to rescue Milan!
      Management to get their heads out of their asses and sign DE Zerbi now!

  2. From the 11 managers since 2009, Inzaghi, Brocchi and Giampaolo were absolutely the worst.
    Allegri is the biggest fraud of a coach in serie A. He has 5 or 6 scudetti but he was on teams that had no competition in the league at the time. At Milan he had prime Zlatan, Thiago Silva, Pato etc, won in the 1st year and lost the scudetto to the worst Juventus to ever win a title. Should have been fired after that season. Those Juventus teams that he coached could have won those scudetti without a coach. We have seen how good he actually is when he doesn’t have by far the best squad in the league.
    I think that Sinisa, Montella and Gattuso actually did a decent job but didn’t get enough time, considering the conditions they worked in. Pioli isn’t better than them. They just didn’t get more than a year to prove themselves, like Pioli who got saved by covid. Especially Gattuso, who had the team finish 5th, 1 point behind 3rd place in 18/19.
    From the coaches that they have been connected to Milan’s job, 2 jump out to me and 1 who is high risk but also a high reward.
    Motta is my n1 choice, been that for 6 months now. His team play very compact football on offense and defense. He has done great Job at bologna with bunch of young and unknown players. If he goes to juve, Milan will regret holding on to the end to Pioli. At 41 he is a complete coach unlike De Zerbi.
    2nd is Conceicao. In the way his teams play and are solid and compact offense/defense he is similar to Motta but with much more experience in a big club and on the biggest stage. Won in Portugal several times over and his team played very good football in UCL all these years. We seen him dominate Milan 2 years ago and Inter last season. In both games his team was better than Inter, but they missed a ton of chances.
    Marcello Gallardo is the high risk coach. He was great at River plate. They played great football and he launched the careers of several young stars. But he has never coached in Europe and has no ties to Italy. He will need to be given time.
    The rest of the names mentioned, there is very little difference. De Zerbi is no better than Fonseca. He plays hipster football but his defense is worse than Pioli’s.
    Fonseca gets a lot of criticism for his time at Roma, but he coached them during the covid season when they finished 5th and in his 2nd season there was a new ownership, while the season started late and the schedule was packed. His 5th finish is the best Roma finish over the last 6 years.
    I’ll rather have Abate than Van Bommel.
    If Conte was a stable person I wouldn’t have mind him as a coach but we know his track record of getting fired after at most 2 seasons.
    BTW, it says that big teams are lining up for De Zerbi but no one is interested in Fonseca. Milan, Bayern, and now Chelsea needs a coach. Why is no one hiring De Zerbi if he they are all lining up for him? Same goes for Conte? De Zerbi isn’t mentioned as an option to replace Pochetino.

    1. I agree for the most part.

      I think Motta is a better option than Conceição for sure. I think Fonseca is “poor man’s Portuguese Pioli” as he has been called and is a terrible option frankly.

      I think regardless of Conte’s “stability” as you call it, even if he were to come in for a year or two, he would build a solid backbone for Milan to further build upon. You can argue current Inter and Juve were both built on his back.

      So for that reason I wouldn’t mind Conte’s inauguration. But he wouldn’t be my first choice.

      I think honestly Motta to Juve is done. I think Lopetegui, Fonseca even Conceição aren’t really looked at by Milan. Neither is Romero or MVB.

      Again, I just think that Milan already has already picked Conte and the fact that every time his name comes up the media are quick to note that “Milan” aren’t interested in him.

      But I’m just speculating based on what ISN’T being reported in the media.

      1. Do a little Google search and compare their careers.
        Both of them coached in serie A and the Ukrainian league. They both coached the same team. See who has better record.
        Speaking on his
        countryman, Capello said: “I
        would put De Zerbi in the
        third tier. There is a lot of
        talk about him as one of the
        top coaches because
        Guardiola sponsors him, but
        this year he is tenth or
        eleventh in the standings.
        What have you won in your
        career? Let’s look at the CV.
        So far, however, no one has
        come forward despite his
        name being linked to the
        benches of the big clubs.”

        1. Well thats a very unfair comparison. Managing Milan from Kaka era and Milan from banter era is not the same even if it is the same team. Same for Shakthar. Also De Zerbi has managed much smaller team in Italy. Which by the way was fighting for Europe spot with him and now without him are getting relegated.

        2. “Do a little Google search”. This just proves how clueless you are. RDZ is miles ahead of Fonseca. Also with 44 years he is still upcoming coach unlike Fonseca who is 51. What do you think he needs to win with Sassuolo and Brighton ?
          He secured place in front of Conte Tottenham and qualified for Europe with Brighton squad that just sells players. In the last 13 months Brighton earned 400+ millions from sales now go figure. Fonseca missed direct qualification to CL in much poorer Ligue 1 with one of the best teams in that league.

      2. Its a simple stat.
        Serie A: Fonseca has a better result with Roma than De Zerbi with Sassuolo
        Ukrainian: Fonseca won 7 trophies, De Zerbi only 1. Both of them managing Shaktar
        Other League: Fonseca won in 2 trophies in Portugal and De Zerbi has 1 good season with Brighton

        1. You can not compare Roma with Sassuolo, as you can also not compare the Shaktar time, Fonseca was 3 years there and De Zerbi just one.

    2. Allegri won Scudetti against Sarri’s Napoli!

      In 17/18 his juve team needed 95 points to win the scudetto against Napoli’s 91. He also lead his team to champions league finals.

      Sacking Allegri was a huge mistake which again handed someone to our rivals.

      After that I agree about Sinisa, Montella and Gattuso and they actually were responsible for developing Donnarumma, Calabria, Locatelli and Cutrone before the club gave up on the latter two.

      I agree with your ideas about who the next manager should be except I do like the vibe around De Zerbi.

      It’s all guesswork/a huge unnecessary gamble so we’ll see what happens.

    3. Succinctly said! You have said it all, bro.These amateurs at management will definitely mess things up!

    4. Nah Allegri brought the PS on the field repeatedly, if S. Inzaghi would be as good as him in that they would hsve more than one Scudetto.

    5. Seedorf had a positive impact. Win against Juve AND Inter if memory works.

      He said 2/3 of this team Is not Da Milan. That’s why he was shown the door.

      Montella had Montolivo playing like the fine player he was before injuries.

      I think Seedorf would’ve stopped all those years of misery…

  3. Pouch just became available. It would be ideal IMO. He’s a yes man and hood at developing young players. Can work with shoes strings budget

  4. As a fan of the works of GRRM; one of the quotes about the birth of a targaryen comes to mind on Conte. A coinflip by the gods for genius or pure unadulterated madness! Hiring him equals either new heights or as yet uncharted lows for Milan. And most likely goodbye Pulisic, RLC and Tomori who were surplus to his requirements @ his Chelsea. Everyone below 26 ditto! Also, its a choice between Rafa and Theo at LWB. Most likely Theo unless Rafa can suddenly pull off a great Dumfries impression. Bye bye RL10 unfortunately. Finally, I’m willing to bet my left nut our new No.9 is a burly, bald, stormzy lookalike, over the hill journeyman with zero technique currently plying his trade at Roma. In summary, Signing Conte will maybe win us the 20th or probably f*ck us but at-least we’ll get to 20 before everything implodes in a spectacular fashion! Cardinale has no idea the shitstorm he is potentially unleashing in Antonio conte..lmao!

    *Seedorf was a better coach than everyone except Montella, Rino and Mohajlović (RIP) during the banter era. We should Everyone else did their best to bury us with Giampaolo ready to piss on our grave! Lol..

  5. I’d be excited above De Zerbi – not based on anything tangible, just a vibe thing.

    The whole thing is a lottery – we could hire Conte and watch him implode as we go out at the group stage of the UCL; we could hire De Zerbi it could become the start of a dynasty.

    Or we could keep the man who has just delivered 2nd place and back to back champions league qualifications.

    1. Keeping Pioli wouldn’t be a bad option imo with all the unconvincing names floating around. But at this point, with Pioli pretty much talking in press conferences about the end of his tenure, it would be a a total farse to keep him. I would still keep it is a viable option on the table tbh.

      1. Well the Pioli situation is entirely the fault of the directors.

        And they pushed him out in the knowledge that we were also losing Kjaer and Giroud.
        Just like they sacked Maldini and sold Tonali in the full knowledge we were losing Ibra.

        Had they any sense they would’ve given Pioli another season to further stabilise the club before planning the hand over to A Guardiola (not THE Guardiola – someone of that calibre).

        But they panicked.

        And we could well end up further undoing all of the work from the past 4 years.

        But still in 4 years time we’ll be back – I tells ya!

    2. I think the vibe of De Zerbi is so strong because Milan fans have seen this before, when it was a resounding success.

      I am pleased that comparisons between RDZ and Sacchi are being drawn because, to my mind they have been quite obvious for some time (both good and bad).

      Starting with the negative similarity, it’s the scope of the unknown. I’m not anti-RDZ, by any stretch, but I’ve definitely been on the side of favouring Motta over RDZ, in a comparison of realistic top quality candidates (where Xabi Alonso and Naglesman would also be really good fits for Milan right now but have never really been possibilities). RDZ has not really over-achieved anywhere, not outside of what could reasonably be expected of the squads he’s had. He’s also never really faced adversity, other than bleeding goals with Brighton this season – and now he’s out.

      Sacchi was about as unproven as it gets for an appointment of a club the size of Milan, he was virtually a complete unknown who had never coached in a top flight before.

      What we know about Sacchi now, that was not well known or appreciated at the time of his appointment, was that he was at the forefront of the tactical evolution of the game. As is also teh case with De Zerbi, the tactics were seen as naively / recklessly attacking by convention (although convention is much less conservative now).

      However, Sacchi’s tactical / technical quality was something that he could only really prove once in the Milan job. One of the key differences in favour of RDZ is that he has a known history of having been at the forefront of the tactical side of the game while coaching in the Serie A and the EPL.

      They’re also both very hard task masters and do it as coaches who had no standing or no significant standing in the game as players. Not having standing as a player is important because the coach cannot fall back on that standing for credibility. Particularly while young, and relatively unknown, his job to sell new ideas is more difficult.
      To get buy-in at a young age is a mark of quality, being able to clearly articulate and explain ideas and also an ability to relate (even if not personally, in a way that produces good results).

      Of course none of this means that RDZ will end up as successful of Sacchi or even seen as one of the great coaches. Just because a coach is young, unproven and comes up with some good ideas does not mean he’s the next superstar coach. But all we can really do is measure these guys against what we have seen in the past.

      Galliani and Berlosconi trusted an instinct almost 40 years ago and it was fundamental to a 30 year period of success. Almost 40 years later they were faced with a similar decision and plucked a similarly obscure Palladino out of the youth system to coach newly promoted Monza sitting dead last after 6 games with 1 point – and found another of the most promising young coaches in the process.

      They made some bad choices during the Banter Era, but the key point of difference picking unknown quantities in that era was that they were picking names, not coaches. But I find myself wondering what they would do in this situation. Would they be picking mediocre experience when faced with one the biggest talents of the generation or would they produce the next Sacchi, Capello, Ancelotti or Allegri?

      1. Great analysis particularly the part about their lack of standing.

        Whilst a few great players have gone on to be great coaches many have struggled.

        I remember reading how Gullit as a coach used to become frustrated his players could do what he did.

        Most of the top top coaches had pretty ordinary careers.

        If we hire De Zerbi I’d go into the season with cautious optimism, hope and goodwill. It’s harder to say that about some of the other names we’re linked with. Conte will make me miserable and then I’ll just have to hope I’m wrong.

  6. I don’t know why, but I see us taking 3 goals from Torino with this guy. And reports say he’s a somewhat problematic character. If we’re looking into problematic characters, I say go all in for Conte. At the very least, he’ll get our defensive game sorted.

    1. What’s there to talk, they’ll sell Inter as fast as they can to some filthy rich Arab and they’ll continue to dominate while we’re winning balance sheet Scudettos

  7. Just want to know what most people think. Would you guys keep Pioli for one more season if that would mean we can get Klopp or Guardiola next season?

    1. Wouldn’t keep Pioli for one more second after the last whistle is blown Saturday.
      And there is a snowball’s chance in hell for Milan to get Pep or Klopp next season or any season anytime soon.

  8. Ancelotti came to milan with raw ability and the rest is history. Milan can do it again with de zerbi. Who knows? Motta i think already with Juve.

    1. What

      Ancelotti won Uefa cup, Italian cup, and uefa super cup with Parma (!) 1998. He launched Buffon and Cannavaro. He also won Intertoto cup with Juventus 1999.

      1. Whatt..

        As a coach he only win with juve uefa intertoto cup 1999 before joint milan. In that era, Intertoto cup thats 3rd / 4rd tier in european championship. And dont forget, buffon and cannavaro already steady with previous parma manager, the legend Nevio Scala.

  9. Motta, De Zebri, Conte, Conceacaio…..

    But we will end up with Fonseca because we waited and we are cheap and we want a yes man who won’t ask for anything ($$$).

    TY Redbird. TY🤮

  10. I am not sure Pioli will be sacked. He is cheap on salery, a yes man and is a guarantee for the 5th spot, which is enough for CL which is exactly the ambition for the club.

    Pure business, but from now on 5th place or above is the ambition of ACM. An occasionally Scudeto is of of course nice and boost the fanbase, but for the owenership CL qualification is the goal.

    Get used to it.

  11. For those who’d like Poch (I sure don’t).

    “Pochettino, who was hired last summer on a two-year deal, was frustrated in his attempts to be given more power and it was decided it was better to bring an end to the relationship rather than risk the possibility of a major fallout next season.”

    Not really a coach to Cardinale’s taste now is he.

  12. I feel like there’s there’s nobody that’s signed and our real plan is fonseca and he will sign soon. That right there tells me everything I need to know about the ambition of these owners. All these great coaches available and you go for probably the worst one on paper who is probably not an upgrade to pioli. What a waste.

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