Devil’s Advocate: The magnitude of timing – the shadow that will loom over Pioli’s reign

By Oliver Fisher -

The general consensus is that Stefano Pioli is entering the final few months of his tenure as AC Milan’s head coach. While the parting can and should still be amicable, it wasn’t supposed to go this way.

There are of course exceptions to everything, but a quick scan across the newspaper columns of reputable journalists and the Milan fanbase on social media produces the same optic, and that is that it is time for change.

What exactly do we mean when we say it shouldn’t end ‘this way’? Well, it can be broken down into two quite simple statements: that Pioli may be remembered more for his losses than his wins, and for what he didn’t achieve rather than what he did.

This will not be a hit piece on the current Milan coach, because as mentioned in the introduction the desire of everyone should be for this to be as well-meaning a separation as it could be well-timed, i.e. at the end of the 2023-24 season.

However, all we can do is lay the facts bare. As it stands, barring a deep run in the Europa League where the likes of Liverpool and Bayer Leverkusen await as fierce opponents, the Rossoneri will end Pioli’s almost half-decade tutelage with one trophy to show.

What a trophy it was, by the way. Every Milan fan who has forgotten what the team achieved under the 58-year-old should watch this video and relive all the emotions we felt during that incredible Scudetto win.

The last-gasp victories, the incredible defensive record to end the season, the highs of the wins against Inter and Napoli – none of that can be erased from the history books and all of it came under the coach that currently stands in the dock.

No matter what happens from now, Pioli will remain the coach that ended the Scudetto drought, that regained a Champions League place after seven years of absence and reached a semi-final, as well as building a young and fun group, an exciting playing style and developing many talents.

Rafael Leao, Theo Hernandez, Fikayo Tomori, Ismael Bennacer, Malick Thiaw, Pierre Kalulu and more – virtually nobody now considered a top player at Milan were at this level before they had Pioli as their coach, be that correlation or causation.

Moreover, this was all done with style, as a polite and respectful person both in the media and in dealings with the management, a detail always greatly appreciated by Milan’s ownership who value such a level of professionalism.

The merits are economic as well as sporting because the two go hand-in-hand. Milan registered a profit in the 2022-23 accounts, something that hadn’t been done for over a decade, and that was largely thanks to Champions League prize money.

Yet here we stand, with the momentum of that incredible title triumph having slipped through the cracks and on the verge of a second season in a row that will evaporate into being very forgettable.

You might be question how the 2022-23 campaign could be classed as forgettable given the run to the final four of Europe’s top club competition, but we all know what happened at that stage and Milan are a club that should have high standards.

This is not a club at the height of its powers like in the 1990s and 2000s, but at the same time it must remain ambitious in an almost cut-throat way. Winning one trophy per season should be the bare minimum, especially given the platform that the league win built and the financial situation compared to rivals.

Instead, we are told to accept by those at the very top of the club that simply finishing in the top four is a trophy-like achievement that should be celebrated. That’s perhaps something to dive into separately, though it doesn’t take a nuclear physicist to know this will not wash with a very demanding fan base.

Thus, we come back to Pioli’s current status, and the notion that he will be remembered more for his failures in big games rather than ones that the team won.

There are only three coaches who have managed more games than Pioli in Milan’s entire 124-year history, and he stands at 1.89 points per game which is far from a bad return (higher than Max Allegri and Alberto Zaccheroni, for example).

The 2019-20 season was a strange one, given the dire situation inherited after Marco Giampaolo’s brief spell and the pandemic, and the post-lockdown run saw Milan play some of their best football in the best part of a decade.

The following campaign saw Milan fight hard for the title and ultimately lead the way for over half of it. Then, damning defeats against Juventus, Atalanta, Spezia, Inter, Napoli, Sassuolo and Lazio turned a title pursuit into stumbling over the line for a top four spot in the final round.

In the Coppa Italia, the Rossoneri lost a derby (something you will sadly read a lot) in the quarter-final, while in the Europa League they outplayed Manchester United over the two legs and yet fell at home after failing to score.

Even in the Scudetto-winning campaign, it slips to back of the mind that the Champions League campaign ended with just one win in six games.

Yet, that win came in the penultimate game against Atletico Madrid and made the final one at home against Liverpool must-win. Milan lost 2-0 against a heavily-rotated side in front of a packed San Siro, thus finishing bottom of the group.

How did the Coppa Italia go? Another loss to Inter, and this time it wasn’t close. The previous year it had been after extra-time, this time it was a 3-0 aggregate defeat in the semi-finals (you’ll read that again too).

Last season, Milan were naturally expected to put up a strong defence of their Scudetto. While Napoli were virtually unstoppable and deserve credit, the losses to the Partenopei, Lazio (a 4-0 hammered), Sassuolo (5-2 at San Siro), Inter and Fiorentina again opened a crisis.

Pioli’s men went on a charge to the Champions League final four and obviously the performances against Spurs and Napoli – particularly in the first legs – should be applauded. The 3-0 loss to Inter in the semis was so comprehensive that it ruined the run for many.

The Diavolo have won four of their ‘big games’ so far in the 2023-24 season against Lazio, PSG, Newcastle and Roma. That 5-1 derby defeat against Inter seemed to establish an air of inferiority that has remained ever since, and the home loss to Juventus was a very bitter pill to swallow.

Champions League draws against Newcastle and Dortmund were what set Milan back to begin with, as did the awful 3-0 loss in Paris, but the 3-1 home defeat to the German side was the nail in the coffin when it should have been so different.

The two recent games against Atalanta are actually emblematic. A gut-wrenching late defeat in Bergamo was followed by a good run of form, and then La Dea celebrated on Wednesday night after ending yet another of Milan’s trophy quests at San Siro.

This brings us to the bottom line: the defeats may not have been plentiful, but the timing of them is what was so damaging and continues to be so.

Hope remains that Pioli can do what he has always done when under pressure: stabilise with positive results, pull out a run that many didn’t think he was capable of, and end the season with just enough to keep him in the job.

However, we can’t shake the feeling that the credit in the bank has run out. Milan are a club that must be judged by winning the biggest games and not filing them under ‘what might have beens’ constantly.

Whether than next step comes from an unrelenting and driven winner like Antonio Conte or a less proven coach who simply has fresh ideas like Thiago Motta is not a decision we are paid to make. All we can do is thank Pioli for the memories and take the next step.

Tags AC Milan Stefano Pioli

41 Comments

    1. If we get Conte then within 6 months you’ll want Klopp.

      Enjoy the season and stop worrying about the next one before it’s started. Time will have its way with Pioli; like it will with all of us.

      1. What are you enjoying? Battling to even qualify for next years CL or being out of it already. I’m really curious what do you enjoy more.

        1. I enjoy going to san siro and having a day out at the football, although I’m based full time in northern England now and married with kids so it’s only a few times a year these days. Or watching the game with my lads on the tv and enjoying the banter as they’re both Man City fans. I enjoy the hugs and lows of being a football fan.

          We’ll finish 3rd, which will do and will be forgotten by June. We might have a decent run in the Europa which would be interesting.

          Pioli won’t be here next year so probably deservedly so, so you’ll get what you think will be a magic wand in the end.

    2. Yeah, won’t Conte be great. We’ll have boring football, him whining and complaining about not having enough players, blaming everyone but himself for every loss, then leaving the club in debt when he rage quits or gets fired in a year and a half. Can’t wait.

        1. If you think Conte is the solution, you haven’t been paying attention and should take a break from posting, because you’re embarrassing yourself.

    3. Conte is a top top coach no doubt, a meticulous professional through and through. The problem is that he always seems to get in a fight with management, and it doesn’t take him very long either.

  1. I haven’t checked the news all day and actually thought he’d been sacked for a minute.

    All feeling a little heavy handed this now. If the board have said they’ll assess in the spring we let the man do his job and assess in the spring, perhaps?

  2. This has to be Pioli’s unluckiest season as coach ever. An unfathomable amount of injuries, stars underperforming, plus refereeing decisions that make your teeth start chattering… I agree it’s time for him to move on at the end of the season though, before the whole squad comes down with typhoid.

      1. I don’t understand the people watching this record of injuries, thinking that this is unlucky and that it will “somehow” stop after the players come back.
        This crisis pretty much started with Pioli and Osti and I don’t understand how the management doesn’t adress that.
        Muscular injuries can be pretty serious and destroy a player (you can already argue that Bennacer is no longer the same) and with us it always seems that the injuries are just waiting to happen.

  3. As Harvey Dent said:
    You either die a hero or you live long enough to see yourself become the villain.
    Something that Spalletti understood and Pioli hasn’t.
    Spalletti knew that he over achieved, caught lightning in a bottle, took advantage of the better teams having a bad year and realized that he won’t be able to replicate what he did and that is only downhill from there. He knew his and the teams limitations.
    He quit and left a hero.
    Pioli scudetto success was as much, if not more, thanks to circumstances. Juventus fell off the map, inter lost their 3 best players and the best coach in the league, and still they had to self-destruct, which allowed Milan to sneak in and win the scudetto.
    Pioli saw Bayern and Klopps style of high press and counter attack, he implemented it in serie A and it worked for about 2 years until the rest of the league caught up to it. After the league figured how to counter that style, Pioli as limited as he is failed to come up with new ideas. Or, he came up with the 5-0-5 system where he completely leaves the middle of the park to the opposing team.
    Initially he did a good job and he will always have the 19th scudetto as a memory but he has overstayed his welcome. He has reached his limits and can’t take Milan any further.
    Should have been fired already last season after he led the team to the worst month in club history and turning Milan into Inter’s easiest victim. The Feb 5th 1-0 loss to inter was the most cowardly performance I have ever seen from a Milan side. It would have been more honorable to forfeit that game than to step on the pitch and hide in your own half for 90 minutes.
    Let’s hope that keeping him until the end of the season doesn’t cost Milan top 4.

    1. So teams should change manager every season?

      Most successful teams have held onto their managers for extended periods.

      Napoli didn’t overachieve last season. They were one of the best teams in Europe even if it doesn’t fit with the imaginary league table in your head.

      1. Pioli has been a Milan coach since 2019. I know you like to live in the past but in the present time we are in 2024.
        Does that sound like someone is asking coaches to be replaced every year? 🤔
        Most successful coaches have held their managers for extended time, that is true. But reality check, Milan is not a successful team. Stopped being that in 2012. One exception trophy doesn’t change the fact.
        Pioli 4,5 years at Milan 1 trophy.
        The man who is his father, Simone Inzaghi, 2 years at inter, has won 4 trophies and schooling Pioli in every derby.
        Milan has won 2 trophies in 12 years, but you are talking about a successful club.
        Napoli didn’t over achieve?
        In the present time, that you don’t live in, Napoli are 9th. 20 points behind the leaders Inter, with literally the same team.
        Just like Milan, who finished 5th last season, 20 points behind the fluke Napoli.
        That big drop off from one year to the next suggests overachievement and a fluke success. If Spalletti believed he can defend the title, he wouldn’t have quit.
        And you are right, Milan fans don’t deserve Pioli. The lack of appreciation is disgraceful. He should just show us ,ungrateful fans, what we will miss and just quit. Leave us to our own devices Stefano.

        1. Inzagi can win 100 derbies against us, he still achieved less at Inter than Pioli at Milan. The coppa Italia is a legit trophy (unlike the super cup), with history, tradition, ect … but two cups don’t equal one scudetto, never have and never will.

          This is not to say that Pioli should or should not stay. It’s just facts.

          1. if let’s say (hope not) inter wins the scudetto this season (which is very likely), what will be your analysis be then ? Because you are correct “so far”, but in the event that what I described happen, he will be a coach that lost 2 coppas, 1 scudetto, 1 super cup and allowed inter to get to the UCL final while also losing 5 derbys in a row and still counting.
            I know that what I say is so far speculative, but it is possible.

  4. I appreciate the Batman reference. I think a former Milan legend would do you better:
    “Coaches are like fish; after a while they pick up a bad smell” – Giovanni Trapattoni

  5. So many ‘fans’ don’t deserve Pioli.

    The lack of appreciation is really a disgrace.

    It seems computer games are to football what porn is to sex. They set unrealistic expectations.

    1. Is Pioli going to get better? No? Are our opponents going to get worse? Maybe?

      Love Pioli up until last season. Until I saw such a regression in January. Something that I have been right about, he can’t overcome it.

      At a certain point we have to change course.

    2. “The lack of appreciation is really a disgrace.”

      Like the lack of appreciation for the club by you? Always b*tching and criticizing how the club ruins and even destroys players. Coming from you…? Good one! 🙂

  6. Posted a version of this before but it bears repeating here. I’m quite indifferent to if he stays or goes. This is going to sound Pro-Pioli but it’s not. But I do support the coach and as always whoever plays on the pitch:

    Results: First of all Pioli is one of Milan’s winningest coaches of all time. Right up there with Capello, Ancelotti and Sacchi. And he’s done so with a VASTLY inferior squad than the aforementioned 3 legendary coaches (only Mike may get into those squads, the rest don’t even come close). This alone makes him vastly underrated. We dont bad talk, Capello, Sacchi or Ancelotti, do we? So why do we have so many questions about Pioli?

    Style of play: we had admittedly better gameplay earlier on with Pioli as a coach — referring here to the post COVID period for about 2 years straight. We were absolutely the best team to look at with a distinct playing style and high pressing game. Unfortunately, with high press teams (see Pool, Barca back in the day), eventually players become tired and the teams need to refresh. Both the aforementioned teams declined until they were able to replenish their squads again. Replenishment is directly related to the funds you have to do so and because we dont we have a slower rate of replenishment. But we can’t deny that we have had a nice style of play. And even now we still are a top 5 scoring team in the league. Its true we lack what we had before but that could be due to tiredness and lack of innovation in tactics. It could also be win fatigue… we’ve been accustomed to winning once more so we are more critical of the team. However, when we have our full strength team, we play very well. This is a very far cry from the banter years where we had absolutely zero ideas. Added to the fact that our offense is so good, teams automatically close up (except Napoli and a few other attack minded teams), and our beautiful game takes a hit. (Earlier on we had the luxury of being a team in banter years shadows so we weren’t taken as seriously)
    Further to this we changed our formation to 433 which is a distinct style. With the 4231 you can do more things. Do I like our style? While I think we can do better I’m not sure another coach can do much better unless he’s one of the absolute top coaches (Pep, Klopp). For the pay bracket we’re working under …

    Player development: Pioli has developed players, whether it was by force (Kalulu, Thiaw), by luck or intentionally. One can’t deny that Theo and Leao are much better than when they first arrived and are sought after by big teams. There are many examples of this…Tonali, Bennacer, Tomori, even Diaz. When given time, there is clear growth. Of course you can’t expect all incoming players to develop at the same rate and there are examples where it didn’t work out (Saelemakers, CDK). But the core starters have improved under him. And he gives youth players some game time. We have never been a club that developed youth and progressed them into the first team so we’re making headway in this sense. Calabria was the only youth product that really “made it” since Maldini and that was almost 40 years ago.

    I’m not saying we should never change our coach but the lack of respect for a coach who has brought us much is quite disgusting. Do I get frustrated at how we play sometimes? Absolutely. Do I think Pioli was in over his head about changing formation, tactics and declaring he had the players he wanted? abso-friggin-lutely. Do I think we should change coach during the season? Definitely no. Do I think they should change coach in the summer? That’s where I seriously hit the pause button. We need to reflect on what’s available out there and also know that by hiring a new coach….things will take time….. which is not available with this fanbase.
    I don’t believe there are many coaches who can bring a team, much less a top team that has incredible amounts of pressure, to third place without a centre back pairing. I don’t believe any of the other coaches below 3rd place are automatically better. The grass is seemingly greener on the other side. Motta has done well but how many have actually seen his team play? I believe people are tired of what they’re seeing now and thinking a change of coach can cure these ills. Motta’s facing the same issues top teams face when they become dangerous – opponents are beginning to close up and park the bus against BOLOGNA (as evidenced by their last 2 games). And so we’re back to square 1. And again I’m not against a new coach but think about having to do better than a consistent top 4/UCL spot, top 4/5 goals scored, Scudetto credentials and so on. These are not simple things to achieve. And I think as fans we’ve gotten in over our own heads. Don’t take things for granted

    1. One of the things I learned a long time ago, if you don’t like the direction you’re going, change.

      We should have changed last season. However Maldini got overruled.

      1. Does that apply to the directors too? Lol Maybe that’s why they didn’t want Maldini. They wanted to do it their way and this is their way, whether we like it or not

      2. We’d have gotten Pirlo or god knows who. Just the fact he was talking to Pirlo about taking over means he doesn’t know what he was talking about.

        1. Like I said and if you bothered reading I am not for or against a change of coach though I am admittedly leaning towards stability wink wink. I couldn’t care who we were linked with, I’m just supporting who we have and who we know. Pirlo might have flopped,.Pirlo might have done wonders. If we get Pep Guardiola he might flop or do wonders. Insert any name there. That’s not to say don’t ever replace a coach. But my question is, are we really going to do better than current. We are third. It means the next coach HAS to be in first or second place and so on. These are not easy feats which I think we’re taking for granted

    2. Very well said.

      Although those legendary squads weren’t as legendary as legend has it.

      Daniel Massaro played upfront. Nowadays he’d be playing in Serie C.

      There were some very good players, world class even, but the key to our success was that we were a tightly knit squad that played together for years (25 in the case of Maldini).

      This constant talking down of the current generation doesn’t help. The Scudetto winning squad was really very good. And we dismantled it believing it wasn’t, and it was all some fluke or Ibra (who played fewer games than Krunic that season – yikes).

      If we must live in the past cannot not be 2 seasons ago?

      1. Yes I believe our Scudetto winning squad was good. The problem as you said we didn’t value keeping them together unfortunately. We needed to add incrementally, not dismantle. Imagine Kessie, Tonali, RLC, Benny with Krunic/Adli backup. That’s a solid core. Pioli has had to deal with a constant decline in squad quality almost each year and still produces results

    3. You typed a very lengthy and admittedly good post, so I think I should take time to adress some of your points bit by bit.
      “Results: First of all Pioli is one of Milan’s winningest coaches of all time. Right up there with Capello, Ancelotti and Sacchi.”
      I’ve seen this post before and I somewhat agree, but by winningest do you mean in terms of winning ratio ? games won ? or titles won ? Because in titles won he is right behind Allegri actually and won as much as Zaccheroni. The 3 coaches you named all have won at least 1 UCL. In winning ratio and games won you could say that in Sacchi and Capello era, we played 30 and 34 games in serie A (less games against tomato cans), the win was 2 points…. I do think Pioli is right behind Allegri and is in the top 10 greatest coaches we’ve ever had, but it also has a lot to do with us not having 10 great coaches in our history.
      “Style of play: we had admittedly better gameplay earlier on with Pioli as a coach — referring here to the post COVID period for about 2 years straight.”
      Correct. I did like the 2019-22 Pioli, but his problem IMO is not the team and style he created, but rather is inability to adapt once that strategy stopped working. It’s a bit like a one-trick pony, once his trick stopped working, he couldn’t do anything. Also without quoting the rest of this segment, yes, we do score often, we pretty much always score, but our current problem is not how much we score, but how much we do concede.
      “Player development” I think this is Pioli’s best achievement, up until this season where most of the players (including Theo and Leao) seem to be regressing.
      The problem is that currently watching Milan and pioli looks like (excuse me for this harsh analogy), watching a corpse, already dead but is still getting stabbed. This is january, the winter window is not even over and yet, we’re playing for nothing. We’re out of the UCL, out of the coppa italia, we’re way too far to win the serie A and excuse my negativity, but I don’t see us beating Liverpool, Leverkusen or heck even Atalanta to the title. At best, we will remain in this 3rd, 4th place to qualify for the UCL (and you can already say that will be actually better than the previous season where we were actually fifth). Pioli probably knows he will probably won’t be here next season, so why should he even bother ? What is he even fighting for ? The players don’t really trust him anymore and he is not a leader type of person or someone willing to have a big beef with someone. He is like a worker who already got a notice that he’ll be leaving soon.
      Now, should we have sacked him last season ? After losing to inter ? after dortmund ? right now ? in June. I frankly can’t answer. There is always this gamble element to bringing a new figure. Even if we bring the best coach, we can’t garantee that we will win anything. Pioli himself came in mid-season. Sometimes it works, sometimes it doesn’t.
      Right now, honestly, I’m more worried about a possible career-harming or even a career-ending injury that one of our players might sustain, more than anything else.

  7. He did well. He doesnt do well anymore. Thats about it.

    I’d like ti very much for him to do well for another couple seasons but it just isnt in the stars. Time for someone else to try their masterclass moves 😀

  8. I never understood why clubs spend more money on a mediocre player then managers?! Personally I would like to see someone like De Zerbi, he is Milanista maybe we can convince him.

    Another one that would transform Milan and loves working with young players plus is able to get the maximum out of them is Marcelo Bielsa, consideri g he took Charge of Uruguay national team just this oast year, I am not sure if we can get him. Not a money issue as he is not greedy but rather where he is now and if we can give him the oroject he wants (worth trying)

  9. If Conte thought Spurs onwer was cheap…well he is in for a surprise should he sign here, with 40 million euros for a market, until they sell his best player and replace him with 7 players 2 weeks before the seasons start, try to scrape the other team’s dead weight, half of them with constant injuries in their last 2 seasons and others f4om leagues where they play disorganized football with poor defense.

  10. damage control…nuff said. a good coach knows when he’s licked.. This coach is living in denial. The statistics they are so proud of show the hard facts: he keeps doing totally crazy stuff and expects exceptional results. Can they please use data or facts to analyze the grit and tenacity of Gattuso or the leadership effect of Baresi, Zlatan or Maldini on the field? so when you dispose of a defensive-minded player and replace him with three players who do not have his traits, insisting that a square peg like Krunic fits into a round hole left by Tonalli, the coach who does that is deluded.
    That strategy backfired. its that simple.
    Tired of all the excuses. If the players are injured and 18 cases are muscular, the data shows you need to change stuff. However, our man refuses to do so and expects different results. Our players are dropping like fleas; some even get injured while warming up!
    We are not, by tradition, a team that jubilates when we survive another top four battle. we are Milan!! the representative of Italian Football in the world!

  11. Hey Giga I’ll clarify your questions. By winningest I mean percentage win rate. So the points era might not matter as much though the number of games would either way he sits about 50-55% win rate. About same as Ancelotti and I believe Sacchi if I recall correctly . Capello though was a beast lol. I think he’s ahead ot Allegri in terms of win %.
    I agree pretty much on all your points…from conceding too much, lack of adaptation (though he did try the 433 and at times 3 at the back so it’s not like he didn’t try, though those seem to be forced than an actual pre meditated plan),.not taking Europa seriously (we’ve never did that and it will.pac tour seire A).
    Except on watching us play. I think fans are starting to get too accustomed again to actually winning games and I don’t think we can do any better than what where we’re at right now.
    I do believe his days are numbered though. Its too much for one person in terms of blame and perhaps his position is untenable

    1. Thank you for the clarifications. I brought that point because I think there is more to a coach rating than his winning percentage, but that’s another subject.
      “I think fans are starting to get too accustomed again to actually winning games and I don’t think we can do any better than what where we’re at right now.”
      But this is a very important mentality for a big club.
      It’s true that on paper we are comfortably third, we’re still in an European competition and we barely missed an UCL in a “group of death”, but if we want to be this big team we ought to be, we always have to seek more. Otherwise we will end up like Manchester United, a big club who somehow accepted this new position of a mere contender for a second place.

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