Gennaro Gattuso knew how difficult the 2018/19 season would be just 90 minutes into it. He had watched his Milan side take a two goal lead over Napoli in its season opener, only to see the Partenopei storm back to win 3-2. He spent the whole match gesturing, shouting, and directing from the sidelines. He stomped up and down his technical area, following the action. Sweating through his black button-front, he was barely able to restrain himself from stepping on to the pitch and putting in a tackle whenever the ball came close. None of his efforts, however, were enough. The final whistle blew, and he stood in the oppressive Neopolitan humidity, looking out across the pitch at the crumbling Stadio San Paolo. Milan’s make or break season began with a gut-punching loss, and he had a hard time making sense of it.
The opening day defeat was difficult for Gattuso to take because the summer of 2018 had been so positive. He had just signed a long term contract after managing to qualify for the Europa League within six months of taking over. The stakes this time around were higher. Gattuso had to qualify for the Champions League. It was up to him to restore the pride of A.C. Milan, the superclub of yesteryear, and he was humbled to have been entrusted with such a task. It was painful for the 40-year-old to see how far the club had fallen since his time there as a player, having won the Champions League twice and two scudetti. He was desperate to return the Rossoneri to their rightful place among the elite.
For the first time in years, it looked as if Milan had a plan. There was a change of ownership, with an American hedge fund, Elliot Management, taking over after its previous Chinese owner defaulted on his loan payments. Elliot might be a vulture fund, but they are shrewd operators. Leonardo was recalled to his former post of sporting director, Paolo Maldini – looking fantastic in a club suit – was lured to a role on the backroom staff, and Kaka started popping up around Milanello. The new owners managed to avoid the incoming FFP European ban, and Milan were indeed eligible to participate in the Europa League. The Rossoneri also brought in Gonzalo Higuain to provide the goals to achieve their lofty ambitions. Gattuso was about to take charge of his first preseason with the club, and everything was in place for Milan to make a push for Champions League football. Securing lucrative European football would dig the club out of the whole it had for itself and set it on a path for success for years to come.
The defeat in Naples highlighted the difficulty of the task, however. After the match, Gattuso was straightforward in his assessment of his team, accusing them of leaving the pitch after 60 minutes. The players had not given their all, and that was the greatest sin of all to a man known for leaving it all on the field. No one could hold anything back if they wanted to achieve their objective for the season.