Stefano Pioli led Milan back to the promised land, guiding a team that used to define themselves by continental conquests to a first Champions League qualification in eight years, but even that could not save him from parental criticism. If the Rossoneri end this season without a trophy, his mother will be waiting to remind him, again, that he has won no major silverware in two decades of senior club management.
“Definitely. Yes, definitely,” he says, leaning in with an unapologetic grin. “And it’s right that she does. In every family there is the hard one and the soft one. My father was the softer one, my mum is the very tough one. That’s how it should be. That’s how you get the most out of someone.”
A discussion of parenting styles feels like a necessary step toward understanding Pioli’s rise. So many players have described him as like a father – from the Milan midfielder Sandro Tonali to the Fiorentina striker Dusan Vlahovic – that you start to think he should write books on how to raise your young ones.
“I do try to look beyond the surface,” he says. “To move past the value of a player and get through to the person. Even if these are young lads who we would call fortunate, they are still young lads with their own lives, their own emotional triggers, personal ties, difficulties.”
He is not one to mollycoddle. If anything, Pioli believes he is more like his mum, “severe, up to the point where I no longer see a capacity to keep improving constantly”. “I don’t tolerate mediocrity,” he says. “And I don’t tolerate us failing to strain to get better.
“If I see players who are demanding of themselves, who are getting better through their own attitude, their own work, then I become more of a, I wouldn’t say a friend, but I give positive support. When I don’t see that level of strain, I have to ask more.”
Pioli was the right man at the right moment for Milan, a nurturing presence at a time when they were committed to rejuvenating their squad. The club had gone through a series of clumsy transitions before his appointment in October 2019; sold by Silvio Berlusconi to the enigmatic Li Yonghong, who ceded control within two years to a hedge fund, Elliott Management, after defaulting on a loan.
There were chaotic spending sprees, with close to €100m splurged in the summer of 2018 on players who did not stick. Only in the past three years can we observe a more coherent policy of recruiting young talent to develop alongside the occasional veteran, such as Zlatan Ibrahimovic, who can offer leadership beyond their contribution on the pitch.
Pioli inherited a group with potential, including a midfield pairing of Franck Kessié and Ismaël Bennacer, Theo Hernández at left-back and Gianluigi Donnarumma in goal. None of it had looked all that promising, though, during the seven-game tenure of his predecessor, Marco Giampaolo. Pioli’s first triumph may simply have been reminding his young players to have fun.
He laughs when asked about the smile that comes across the lips of Milan’s 22-year-old Portugal forward Rafael Leão as he runs at defenders. “At the beginning, it worried me a little. Later I realised that this really was something that just comes out while he is playing, simply what his face does. Then it was beautiful. It’s beautiful to be yourself.
“Having fun is fundamental. That’s a thing that we look for. We try to be as serious as possible, committed and professional. But football is passion, enjoyment. When you train lads who are very young, you need them to put their enthusiasm on the pitch.”
Pioli was supposed to be a caretaker. Milan lined up Ralf Rangnick to replace him in the summer of 2020, only to change their minds as performances improved. Instead, the club doubled down on Pioli, supporting him with further signings. Last January, an English defender, Fikayo Tomori, arrived from Chelsea – initially on a six-month loan.
“I had watched videos and seen impressive characteristics,” says Pioli. “But Fika was a positive surprise in every way. On a footballing level, because he is a defender who has characteristics the team needed – aggression, pace, a capacity to read the game. Then he is an extremely serious lad, extremely calm.
“We were talking before about how you motivate a player. With Fika it was easy because he is always determined, always enthusiastic, always positive, always attentive. With him, truly, our relationship is very simple. It takes few words to understand each other, to develop the whole idea of the work.”
The admiration is mutual. Tomori has spoken about how much he appreciates Pioli’s attention to detail, working on specifics of his positioningThe manager stresses how he has always seen it as his role to take the lead with one-on-one coaching, letting his staff assist with broader tactical considerations.
Pioli believes the sky is the limit for Tomori. “He has grown a great deal in these two years, but he can still grow more. Given how much faster he is than the average defender, sometimes he takes too many risks trying to anticipate an attack too early. He could wait a tiny bit longer and, instead of acting on the expectation of a certain play, he would wait for that play. But being such an intelligent lad, he will get better at that too.”
After finishing as runners-up to Internazionale in Serie A last season, Milan find themselves in a familiar position, second behind their neighbours. They missed a chance to go top when they lost to Spezia on Monday. Milan were denied a late winning goal when the referee blew his whistle prematurely, instead of playing advantage after Ante Rebic was fouled (Spezia scored a late winner of their own deep into stoppage time).
Even in defeat, the manager found encouragement in the response of players, accepting responsibility for the result instead of berating the official.
“The behaviour of my players was immense,” he says. “They showed respect for sporting values and towards a person who made a mistake. In sport, we all commit mistakes. That should not make us feel superior to, nor less worthy than, anyone else.”
Milan’s next game is at home to Juventus. Then comes the derby with Inter. Pioli calls it “not a decisive moment, but an important one”. His target is for Milan to improve on the 79 points they finished with last season. He had hoped for a better showing in the Champions League, his team finishing bottom of their group behind Liverpool, Atlético Madrid and Porto, but he is able to see the glass half full – highlighting strong performances against the Spanish champions and that many Milan players were making their debut in the competition.
“My young footballers are growing well,” he says. “But soon it is going to be time to stop calling them young footballers, and just call them footballers, ready to compete at certain levels.”
Pioli is a parent with high expectations. If his mother can still scold him after all these years, there is no chance of his players getting an easy ride now.