It was the moment that ensured Guglielmo Vicario and Tottenham Hotspur's journey together would not continue beyond this summer.
The Italian had endured a mixed time at the club, impressing in his first season in north London before beginning to blend eye-catching saves with more unconvincing moments with his feet as well as struggles at set pieces as opposition teams looked to target him.
However, on November 29, Vicario reached the lowest point of his Spurs tenure in front of a frustrated Tottenham Hotspur Stadium. The 29-year-old had conceded Kenny Tete's deflected effort just four minutes into the London derby which stunned the crowd but it was what happened two minutes later that sealed his fate.
The goalkeeper came out to claim a ball on the Lilywhites' left flank, way outside of his box. He managed to do that but then inexplicably chose not to kick it out of play and instead hit a weak pass down the line. The ball eventually fell to Harry Wilson, who curled it back from the touchline into the empty net.
The 60,546 fans inside the stadium let out all of their frustrations in Vicario's direction. The Italian became the focal point for supporters who had paid big money to, at that point, watch a team that had won just three of its past 21 home league matches.
Vicario was booed with each of his next two touches and then cheered sarcastically when he kicked the ball out of play, despite showing character to put himself in the same situation by rushing out as Fulham attacked.
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It was uncomfortable viewing. The Italy international had saved Spurs repeatedly in a bright first half to the season but the supporters needed an outlet to vent their frustration and the goalkeeper, as Davinson Sanchez had found during a home defeat to Bournemouth in April 2023, was on the receiving end.
Publicly Vicario did not hit back at the booing or hide from the glare, coming out to do interviews for the media and telling Sky Sports: "It's part of football. I am a big man, I am quite older. We cannot be influenced by the situation in the stands. The fans have the right to do what they think and probably it is on us to stay more calm and focus more on ourselves."
Privately though he was hurt. It felt like the bond had been broken and with the stopper a popular figure inside the dressing room, it only further pushed a wedge between the players and the fans. That connection would only be resuscitated just when it mattered the most in the final weeks of the campaign and fate would have it that Vicario was not in the team during that time.
On that day in November though, the players were furious at Vicario's treatment, none more so than Pedro Porro. The Spaniard stormed down the tunnel after the game, trying to get his team-mates to follow him, and later posted on Instagram: "Football is emotions. In football, as in life, there can always be mistakes. What I will not tolerate is hearing disrespect from the fans to my team-mates, hence my frustration at the end of the game.
"And we will get up. We remind you, six months ago, everything was so bad. In the end, it is not how it begins but how it ends. To the true Spurs fans, I love you."
It was those final words that stirred the situation as they were the same ones used by Thomas Frank after the game.
"I didn’t like how the fans reacted to that," said the Dane. "They booed at him straight after and also three or four times when he was on the ball. For me that is unacceptable. They can’t be true Tottenham fans. Booing after [the game], fair. No problem. But when we are playing we need to be together."
As with Vicario, Frank's race was run that day as well. It was particularly unfortunate for Vicario because he gave everything to the club from the moment he walked through the doors.
After his £17.2million move from Empoli, the Italian had to take on the mantle from the long-serving World Cup winner Hugo Lloris and in his first season between the sticks in N17, he was among those in the running for the player of the year prize that eventually went to Micky van de Ven.
In his second season he played for an hour on a broken ankle, following a collision with Manchester City winger Savinho - of all people - and was magnificent as Tottenham won 4-0 at the Etihad Stadium. Once he returned following surgery, Vicario had some big European performances. While he had shaky moments in the Europa League final in Bilbao, he crucially made a last-gasp save from Luke Shaw's header, pushing it to safety not long before the final whistle blew and the 17-year trophy drought was ended.
In his third and likely final season at the club, Vicario played for months with a painful hernia problem, keeping more clean sheets in the Champions League league phase than any other keeper. He finally had the surgery he needed after what is likely to be his last game for the club, the 3-0 defeat at home to Nottingham Forest on March 22.
He had put off the surgery amid concerns among some in the club over whether Antonin Kinsky was ready to step in, not helped by the Czech's nightmare evening in Madrid, with Vicario called on to replace him just 17 minutes into that Champions League game.
The Italian knew though that Kinsky was ready to shine in the final weeks of the season and thankfully for Tottenham and Roberto De Zerbi, he was right.
"He has been incredible, impressive, he did unbelievably well. In every game it was not easy," Vicario said of his young successor. "Now it’s easy to say but I was sure of his mental strength and ability. When I spoke to Roberto the first day he signed he asked me how Toni was and I said 'I think he is fully recovered from what happened because in football it can happen', and he showed it," said the Italy international.
"That's the biggest strength he can put on the pitch. I’m very proud of him, he made some really important saves to keep us in the league and he deserved his moment. Sometimes football is downs, I think he had the brilliance to show his ups. Especially in the last two, three games. He did unbelievably for us."
Vicario had also told De Zerbi that he was looking to leave the club this summer soon after his compatriot's arrival, but he was unlikely to fit the new man's style anyway which relies heavily on the ability of the goalkeeper with his feet to make quick decisions with creative passes.
Now Vicario will get to follow in his hero Gianluigi Buffon's footsteps and play for Juventus. The Turin club gave up on trying to prise Emiliano Martinez away from Aston Villa at the weekend and switched their attentions to the Spurs man instead on Sunday.
It will be a loan move with an option to buy the goalkeeper for £8.5million (10m euros), while there is likely to be some loan fee involved as Vicario ties up his deal in Italy on Monday.
After the departure of Cristian Romero and Djed Spence, it is another senior player Tottenham have had to accept a low fee for, Vicario and Romero both departing for far less than the amount they were signed for. Spurs have offset that by making plenty of money on moving on young players this summer. It's just a case of getting players out of the door who are not desperate to be part of De Zerbi's project.
Vicario did ultimately care about Tottenham, something not all its players over the years can claim. Just look at him strangling De Zerbi in the celebrations after Joao Palhinha's crucial goal against Everton on the final day of the season. The club being safe meant everything to someone who knew they would be leaving anyway.
He argued with the Everton bench over various challenges and decisions. At the final whistle he sprinted over to all of his team-mates and roared at all of them for their efforts. He had been on the bench, but was never expected to play a part.
That image grabbing De Zerbi summed up Vicario. He is an intense character and would often berate his team-mates as passionately as he celebrated with them, but he did it from a place of caring about the team and the club as a whole.
He would often speak to the Tottenham academy goalkeepers, right down the age groups, to help prepare them for what was to come in their lives in football and beyond.
His parents Monica and Michele became passionate fans of the club, his mother in particular an outgoing character alongside his quieter father as the two mingled with the supporters in the crowd and on trips to games, home, away and abroad. Like their son, they invested fully in all things Tottenham Hotspur. Now comes a return to Italy for the family.
Vicario might not be remembered in the way his predecessors are in the years to come but he played his part - often through the pain barrier - across 117 appearances for the north London club. Now begins a new era for both him and Spurs.
