As the Juventus players toiled on a waterlogged pitch in Perugia, they knew that the summer holidays had begun for the rest of the Serie A. They were probably also conscious that had the torrential rain come at any other point of the season, referee Pierluigi Collina would have been more likely to postpone the game rather than delay the start of the second half for almost an hour as he had decided to do.

Above all, they knew that Lazio had beaten Reggina 3-0. That meant that they were on equal points with them at the top of the league and, if things stayed that way, a play-off would be required to determine the destination of the Scudetto. So they pressed forward as best as they could, given the state of the pitch. Then, the unthinkable happened.

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From a Rapaic free-kick, defender Calori rose highest of all to head the ball past Edwin Van der Saar. Perugia were in front and Lazio ahead in the league table. Once Perugia scored, the game regained its previous pattern; Juventus pressing hard to overturn the game without actually getting there.

There was too much water on the pitch for them to really make an impact and they couldn’t seem to find the energy to score the decisive goal. True, Perugia were well organised, but Juventus were also substandard. Eventually, the slog came to an end. Lazio were league champions and Juventus runners up. It would be as close as Carlo Ancelotti would come to winning the league title as manager of the Bianconeri.

Once his glorious playing career was wound down with a final season (and another league title) at AC Milan in 1992, Ancelotti was taken on by his mentor Arrigo Sacchi as an assistant for the Italian national team. It was an obvious move for someone who had acted as Sacchi’s coach on the field for so many years.

Sacchi’s four years with Italy were significantly less successful than many had anticipated, even if he did lead Italy to the final of the World Cup in 1994. Ancelotti was there for three of those years having decided to accept Reggiana’s offer to take over as manager in 1995. The club from the South of Italy was an ambitious one and was looking for a quick return to the Serie A having been relegated the previous year. Ancelotti delivered on that desire, leading them to a fourth place finish that meant automatic promotion. For him, the move was a bigger one as, instead of guiding Reggiana, the following season he was placed in charge of Parma.

That Parma side was filled with talented players – Gigi Buffon, Lilian Thuram, Dino Baggio, Gianfranco Zola and Hernan Crespo to name a few – and expectations were high. But Ancelotti proved his worth. Their biggest problem was that they had to compete with one of the best ever Juventus sides, one that had won the Champions League the previous year. Parma almost made it. Almost. A draw in Turin three game from the end of the season kept Juventus just outside their reach and once the league ended Parma were second with 63 points, two points behind the Champions. To this day, this remains their finest ever finish. Ancelotti stayed on at Parma for another year, where they finished a disappointing sixth in the league, and which meant the end of the road for their manager.

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The beauty of Italian football is that a negative season does not necessarily taint a manager’s reputation. It is unlikely that Ancelotti would have returned to management at the very top in any other league but when Marcello Lippi opted to leave Juventus midway through the following season it was him that they turned to. The reception that he got wasn’t the warmest. A banner unfurled in his first game in charge – away at Piacenza – read “A pig can’t coach, Ancelotti leave”.

A run of positive results upon his arrival promptly silenced those critics but it did not win their trust. Instead, at best, it evolved into a begrudging acceptance that for the foreseeable future they were stuck with Ancelotti. Indeed the emotional signalling from a segment was that they would rather see him fail so that they could tell the club that they had been right. It was hardly the best or the most promising start to the relationship.

And yet it could have gone so much differently. Ancelotti guided his side to the semi-final of the Champions League where they masterfully drew 1-1 at Old Trafford against Manchester United. Juventus were the better side for long stretches and seemed favourites to make it to yet another final. Instead, it was United who managed to conquer the Delle Alpi stadium, winning 3-2 in one of the most famous nights of their history. It was a result that left Juventus with nothing to play for except a decent placing in the league. Even there they failed, finishing seventh and losing a play-off with Udinese to decide who went into the UEFA Cup.

This made Ancelotti’s job harder. Not that it was ever going to be any different: he had to face up to the huge shadow of his predecessors’ achievements. During the previous three seasons, Juventus had won the league twice and reached the final of the Champions League on three consecutive occasions (winning one and losing the other two). Matching up to those achievements – let alone exceeding them – was incredibly hard from the start.

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On top of all that there was the psychological fatigue that tends to accumulate among sides who have won as much as Juventus had in previous years. Some players left during that first summer, others were thinking of doing so. Ancelotti had to rebuild both mental strength and the team.

That summer, the Serie A went on a spending spree. Milan bought Andriy Shevchenko, Inter spent big on Christian Vieri, Lazio went for Juan Sebastian Veron and Diego Simeone, AS Roma took Vincenzo Montella whilst Parma went for Marcio Amoroso who had topped the goal scorer’s chart at Udinese the previous season.

Juventus, however, went in the opposite direction. In attack they got rid of Thierry Henry and instead replaced him with Darko Kovacevic. The Frenchman had been a huge disappointment in his brief spell in Italy but would go on to develop into one of the finest players of his generation; Kovacevic on the other hand would leave Juventus after two largely anonymous seasons. Few transfer swaps have worked out as badly as that one did.

And then there was the goalkeeper. Angelo Peruzzi had opted to follow Marcello Lippi to Inter and to replace him, Juventus went for Edwin Van Der Sar. It seemed like a sure thing as the Dutchman had excelled for Ajax whom he had helped to the title of European champions. In Italy, however, he never really found his feet and he too would leave the country after just two error strewn seasons. So low had his reputation fallen that the only club to express an interest in him after he was done at Juventus was Fulham, then newly promoted to the Premier League.

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Despite everything, Juventus were top of the league well into Ancelotti’s first full season in charge. In fact, with eight games to go till the end of the league they had opened a nine point gap ahead of Lazio. Everything was in their hands. But their lead quickly shortened when they lost in consecutive weeks: away from home against AC Milan and then, significantly, at home to Lazio. Victories against Inter and Fiorentina hinted that the worst was over but then lost 2-0 away at Verona to allow Lazio back in within touching distance.

Still, with one game remaining against a comfortably safe Perugia was seen as a relatively easy win. But then came the rain, the delay and Calori’s goal.

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Ancelotti never really recovered from that defeat. Nor did his team. They came to be seen as a mentally fragile side that could collapse under the weight of expectations. The following season, needing a win against Panathinaikos to qualify from their Champions League group, Juventus instead crashed to a 3-1 defeat in Athens. They lost the league yet again, this time to Roma, by 2 points with the announcement of his dismissal from Turin coming in the half time of the final league game. Few were surprised.

Ancelotti simply couldn’t fix that problem. Perhaps he needed more from his senior players, yet the reality was that his biggest stars were either in decline or still living off past glories. A stronger coach could have changed through sheer force of personality but Ancelotti didn’t have the power to do so.

That highlights why, perhaps, the most significant reason for his failures is perhaps the most mundane: lack of experience. For all the various jobs that Ancelotti had filled prior to joining Juventus, nothing could ever come close to leading the Bianconeri. Success was expected, rather than merely hoped for.

This is where Ancelotti struggled. Of course, he knew from his time at Milan what it meant to be constantly expected to win. Yet back then he had been a player which, from an emotional point of view is completely different to being a manager. As a player you know what you need to do and what kind of effort you have to put in.

It isn’t the case as manager. Not only do you have to think about how the team sets up tactically but you have to get the players in the right frame of mind. A manager has to ensure that every player has the right motivation and energy levels to succeed. Which is not at all easy at a club like Juventus where a lot of players had grown somewhat apathetic given the success they had enjoyed. These players needed motivating but Ancelotti still needed to develop the knowledge of how to achieve this.

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Close to two decades later, the bad taste still remains. In a biography published in 2009, he claimed that he “never loved [Juventus] also because of the welcome that I received from the supporters.”

Contrary to tactics, one needs to live through the experience to better gain a handle on things. Ancelotti had been through hard times at Parma but it was a wholly different experience. Given all that he has gone to achieve elsewhere, Ancelotti’s time in Turin has been written off as a necessary learning experience on his path to greatness.