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

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.