The Pioli Predicament

Milan has had a tough time with coaches ever since Allegri was finally sacked six years ago. After burning three ex-Milan legends and Brocchi, as well as a couple of other coaches, Pioli has come in and offered wisdom, serenity, and stability. He is a good coach, but has not ever won a Scudetto, let alone a Champions League trophy. While we have been waiting on this interrupted season, talk has turned to who should coach Milan next season. Do we make a change? Or stick with what is working? Would he be enough to bring Milan back to glory? It truly is a Pioli predicament.

He's good, but is he good enough to stay?

Not surprisingly, this is a question we have asked of the past few coaches. First, it was Montella. His first season was no better than mediocre, and we wondered if keeping him another season would be enough. That was answered very quickly and resoundingly with the horrible beginning of the 2017-18 season. He was sacked at the end of November, having very clearly lost the plot, as well as too many matches. Also not surprisingly, he was Yonghong Li, Fassone, and Mirabelli’s choice in the first place, and it was their decision for him to stay, as well.

Triple handshake? Try triple nightmare.

He was replaced by Gattuso, who was the third Milan legend to be tested by fire at Milan in the past six years. Gattuso notoriously drew his first match with Benevento, with their goalkeeper scoring a stoppage time goal to give the team their very first Serie A point ever. Though this made his appointment more of a joke than it already had been, his grinta surprised everyone in inspiring the team to do more than expected. In fact, with his record, had he started the season in August, Milan could have realistically qualified for the Champions League that season.

Plenty of grinta, not so many goals, just like his playing career

Despite enduring the change of ownership in 2018, as well as all of the other drama at the club, Gattuso led the team to a fifth place finish last season, one tiny point away from Champions League qualification, and also the best finish since Allegri. Despite maddening tactics and substitutions that took all of the beautiful from the beautiful game, as well as the opposite of grinta when it came to a scoring mentality, had even one little thing gone right for Gattuso, everything would have been different for all of us. Literally one point. (This includes Gazidis’ decision to block Ibrahimovic from coming back to Milan a year earlier.) But at the end of the season, despite the best winning record since Allegri, by mutual agreement, Gattuso left, even forfeiting his salary owed for the remainder of his contract, because it was never about money.

That joke isn't funny anymore

Maldini and Boban decided to trust in Giampaolo last summer, their singular and very tragic mistake. It became very clear very early on that he was not exactly the manager Milan needed. While he had wowed at Sampdoria with delicious tactics and attractive football, he was clearly in way over his head at Milan. Not only did he look visibly nervous, he astonishingly refused to include the newer, more talented players into his starting lineups. His tactics were baffling, and many of the players admitted they were a little confused about exactly what they were supposed to do. With a team that was so young, it was dangerous not only to his career at Milan, but also to the mentality and future of the team. Controversially, Maldini and Boban sacked him at the beginning of October. Although in hindsight, they were simply very wisely correcting an error.

Both ex-Milan coaches already

Enter Stefano Pioli. With wisdom and experience, he set about the daunting task of restoring the mentality of the team. His calming mentality was perhaps his most important quality, and having led Fiorentina through the tragic loss of their captain, Astori, it was clear that he had the mental and emotional skills to deal with Milan’s far less significant mentality issues. Many of the Fiorentina players consider him like a father, and he was quick to try to build personal relationships with the Milan players. In contrast, Quagliarella had said that at Sampdoria, Giampaolo rarely ever spoke to him, despite being capocannoniere that season. Whereas Pioli spoke to everyone individually when he first arrived.

Confident, clear, and calming

On the pitch, he decisively chose a formation, and then was willing to tweak it as needed. The players quickly seemed clear about what the tactics were, and while the results were not immediate, the style of play improved very quickly. It was clear watching the game what it was that he was trying to accomplish, and the confidence of the players grew rapidly. His substitutions have been sublime, almost always making an impact, being very clear about rotation and the physical needs of the players, and often changing the outcome of the match. By far the best subbing we have seen at Milan in at least ten years. Rebic’s resurgence in January, even starting as a sub a few times, was clearly the result of excellent management.

Will he be given another year?

Milan left Pioli’s contract open to a second year, depending on the results of this season. Do they stick with the experience and consistency? Or do they try to shake things up with a ninth manager in six years? Just because Pioli hasn’t won a trophy yet in Serie A doesn’t mean he won’t ever, does it? Or does the club do something like Inter, who sit in third place with a game in hand after paying €12 million for a coach who actually has won before? That is literally eight times as much as Pioli makes, for only a few spots on the table difference. Is it really worth it?

Pioli was given a steep road to navigate, after the mentality issues of so many ownership and management changes. Then the squad changes in January, too. While the signing of Ibrahimovic gave him a nice boost, Pioli laid the groundwork to improve this team, and he is the one who has to manage everyone from a superstar all the way to newly promoted youth players. Then, Boban was sacked just ahead of the pandemic interruption of the season, too. Finishing this season off for all of the teams will undoubtedly be up to mentality. But will that be enough to have him stay on for next year, too? If so, will this group be able to rally around him and help him find his first senior trophy next season? Making the right choice is truly the Pioli predicament.

This post inspired by the music of The Clash’s “Should I Stay or Should I Go?”