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.
Milan struggled to find any sort of consistency over the next few months. Higuain felt too much was expected of him on and off the pitch, and quarreled with Gattuso. The goals dried up. Injuries plagued the squad, and the Rossoneri crashed out of the Europa League group stages. The team limped into the winter break with a series of toothless performances, yet they were still within touching distance of the top four.
After shedding the malcontent Higuain and replacing him with the signings of Krzysztof Piątek and Paqueta, Milan were unstoppable after the break. By the middle of March, the club overtook crosstown rivals Internazionale and found itself in third place ahead of the second Derby della Madonnina of the season. Inter had won the first derby back in October courtesy of a Mauro Icardi winner in stoppage time. This time, however, Gattuso’s counterpart, Luciano Spalletti, was struggling to contain the rifts within his squad and Icardi had been banished from the team. Following Inter’s elimination from the Europa League at the hands of Eintracht Frankfurt, Spalletti had to win the derby if he wanted to keep his job. This was the opportunity for Milan to land a knockout punch on a sworn rival while cementing their hold on a Champions League place.
Gattuso, however, was cautious ahead of the match. He was worried about losing and the effect it could have on his squad’s mentality. He felt the tension in his players, and tempered his words before sending them out to take the field. In the tunnel, the two coaches walked out together. Spalletti was all smiles. Gattuso, though, had a look of concentration; he fiddled with his cufflinks, preparing for the match. The club suit, provided by Diesel, was a different sort of uniform than his playing days and it did not seem appropriate. He was heavier now and greying at the temples but still possessed all the intensity that saw him nicknamed “Snarl” in his youth. He looked ready to lunge.
The referee blew his whistle, and the match began. The tension from the buildup was obvious, and the players, finally able to get at one another, snapped into tackles and contested everything. Gattuso had sent team out with orders to press high, and force their opponents into mistakes. But it was Milan who made the critical error just two minutes in. A mixup between Paqueta and Hakan Çalhanoğlu left their left flank hopelessly exposed. Gattuso watched helplessly as Inter worked the ball effortlessly down the wing just a few feet from him. Alessio Romagnoli, Milan’s captain and stalwart center back, was suddenly left with too much space to defend and stepped out to confront the Nerazzuri attack. He made one clearance, but it wasn’t enough. The ball went back into the box, and Romagnoli, seeing it floating to the back post, hesitated for a split second. And, as a result, he was not expecting Lautaro Martinez to superbly head it back across the face of the goal for an onrushing Matias Vecino.
The Calabrian coach had sent his charges out with an aggressive gameplan, and he gambled on maximum effort and perfect execution from each and every player. He knew the mental frailty in the squad, and he shouted encouragement to pick his team up. He believed in them and their ability to turn this match around with passion and pressing. Unfortunately, the press was disorganized and lightweight, and Inter bypassed it easily over and over again. It was a difficult 45 minutes to watch. Gattuso needed to change something at halftime and sacrificed Paqueta. The Brazilian had looked out of sorts and tired, and everyone on the pitch needed to be at their best to turn the match around.
The second half began, and Gattuso’s changes made a difference. Inter’s midfield had enjoyed a stress free first half but now found it much more difficult to get time on the ball. The Milanisti responded and urged their team forward. They had picked themselves up and forgotten the disastrous first half. After all, as bad as Milan were in the first half, they was only down one goal. With everyone playing with this sort of passion and intensity, an equalizer and winner were sure to come; Champions League football – and thus, the club’s future – would be secured, and it would all come at the expense of their biggest rivals. Expectation filled every inch of the San Siro, from the technical area all the way up to the red girders that framed the sky.
All of the anticipation, however, only made Inter’s next goal all the more deflating. Stefan de Vrij managed to separate himself from his marker at a corner and headed home the second goal of the match. Those in red and black could not muster the energy to move as the Dutch defender wheeled off to the corner flag to celebrate. Milan’s captain could only manage to place his hands on his hips; asked after the season if he could choose a match to replay, this was the one that immediately came to Romagnoli’s mind. The match was effectively over, and so was Milan’s season.
Tiemoue Bakayoko scored his first goal for Milan five minutes later to bring it back to 2-1, but it was obvious where this was all going. Gattuso, drenched in sweat despite the cool spring evening, did his best to challenge fate by throwing on Patrick Cutrone.he young striker could always be counted on to give his all for the cause. His energy and enthusiasm made the crowd believe it was possible for the home side to at least find an equalizer, but Samu Castillejo’s foolish challenge in the box in the 65th minute had fans cursing their own foolishness to believe this team could make them happy. Martinez converted the penalty kick into a death blow not just for the match, but for Milan’s season as well.
Gattuso’s worries over his squad’s ability to recover from such a disappointment were well founded. Despite managing to pull another goal back from Mateo Musacchio, the players began unraveling. Franck Kessie was unhappy with Gattuso’s decision to bring him off and was confronted by Lucas Biglia for his lack of respect as he went to his seat; the two argued, and Kessie had to be restrained by two teammates as Biglia continued to harangue the Ivorian. Andrea Conti, who replaced Kessie, launched into a wild knee-high tackle on Martinez and then sprang to his feet to swear at the downed Argentine.
Meanwhile, Spalletti smothered the spectacle with agonizingly long stoppages for substitution; the fourth official could only smile in disbelief at the impudence of the Inter players as they did not even pretend to make an effort to come of the pitch in a timely fashion. Gattuso watched, eyes bulging, and restrained himself from running over and dragging the malingerers off by their black and blue collars. The final whistle blew, and he strode over to the Inter bench to congratulate them as sportsmanship demanded, jamming his feet into the turf at every step in an effort to rid himself of the disappointment building up inside of him.
The Rossoneri felt the loss keenly and could not put it out of their minds. They only managed one win in their next six matches, and dropped out of the Champion League places. The players lost belief and started showing up late for training. Gattuso was captaining a sinking ship while also contending with a mutinous crew. They would finish in 5th place, just one point behind Inter.
Gattuso took the full weight of Milan’s expectations on his shoulders, but, ultimately, it crushed him. He had failed. “I wasn’t good enough at dealing with the pressure,” he said, “I never felt just like a coach, but rather I felt everything.” His passion for the club made him an ideal candidate for the role of manager, but it also was his flaw; it burned him out, and he did not have enough emotional energy to pick his squad up after the derby. Upon his resignation shortly after the end of the season, he forewent his multi-million euro severance package on the condition it would go to his coaching staff who had to leave with him. Gattuso’s failure to qualify for the Champions League may have cost him his job, but he left with integrity, having given it everything he had. That, in the end, is worth far more to the man than any amount of television money or severance pay, and there will always be a place in football for him because of it.