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Antonio Conte wins titles, but the Awkward One doesn’t connect with Napoli’s fans.

This situation with Tottenham is somewhat unique. Since leaving Siena in 2011, Antonio Conte has had major success, capturing league titles with Juventus, Chelsea, and Inter. As Sunday’s match approached, with Napoli leading the table by three points and only three games left, it seemed like a familiar narrative. Throughout his career, he’s won trophies at every club except for Tottenham.

Maybe Tottenham isn’t quite the powerhouse compared to the likes of Juventus, Chelsea, and Inter, or perhaps it just doesn’t feel the same. Napoli, for instance, recently won the Serie A title. Conte’s tenure at Tottenham spanned 17 months, during which he maintained a solid win record, ranking fifth among Spurs managers. However, his first season ended with a fourth-place finish, and when he replaced Nuno Espirito Santo in November and departed in March 2023, the situation had become decidedly unfamiliar.

Conte’s outburst after the team squandered a two-goal lead, resulting in a 3-3 draw against Southampton, was revealing. It felt brutally honest as he scrutinized the team and its culture. “The Tottenham story is distinctive,” he noted. Unfortunately, he didn’t capture that essential middle phase of making significant progress.

Tottenham remains a challenge. It’s perhaps not fair to judge managers too harshly during their time there. Winning has been elusive, and the landscape is complex—look at Ange Postecoglou, who, like José Mourinho and Mauricio Pochettino, could be on the chopping block soon after any major successes.

Evaluating Conte is tricky. On one hand, his record is stellar; if Napoli claims the Serie A title, it would mark his sixth league victory across four clubs in just over a decade. He also transformed Italy’s national team, guiding them to success and resurgence in dynamics before a heartbreaking exit against Germany in a penalty shootout. Yet, there’s always been underlying conflict and tension in his story, making him a bit of a headache for club directors.

His tactical prowess is undeniable. He typically favors a back-three setup, and this season began with that style. However, as the transfer window closed, new signings like Scott McTominay, Billy Gilmour, Romelu Lukaku, and David Neres influenced a shift. Napoli initially tried a narrow 4-2-3-1 system, featuring McTominay nearly as a second striker; they later transitioned to a 4-3-3 formation with wingers and central midfielders.

January brought its own challenges, with injuries forcing adjustments in the game plan. Initially deploying Lukaku and Giacomo Raspadori up front, McTominay’s role evolved, often drifting to support the midfield while relying on full-backs for width. He excelled in this setup, scoring 11 league goals and becoming a fan favorite—while they might not erect a statue in the style of Diego Maradona, a mural could well celebrate McTominay if Napoli secures the title.

Conte’s adaptability has significantly influenced Napoli’s success this season. His intense style and demands can be a double-edged sword. Passionate yet challenging, his personality sometimes overshadows any respect he earns. Life as Napoli’s manager has always been fraught with difficulty. Historical figures like Ottavio Bianchi and Alberto Bigon faced tough days managing during their title-winning times with Maradona in the late ‘80s. After winning Serie A in 2023, Luciano Spalletti felt so drained that he took a sabbatical.

Even by Napoli’s standards, the exchange between fans and Conte is a bit off. It doesn’t feel warm, more transactional. Expectations aren’t high for club president De Laurentiis to stick around after this season.

Conte and De Laurentiis have had their share of clashes. Although Conte didn’t name names, his comments suggested where his frustrations lay, especially noting that similar issues crop up everywhere he coaches. Despite this, Juve and Inter reached Champions League finals not long after his exits.

McTominay referred to the demanding nature of Conte—both a gift and a challenge. Remarkably, Conte became the first manager to win Serie A titles with three different clubs, excluding the revocations faced by previous managers.

His complex emotional landscape, filled with psychodrama, remains central to his narrative, trophy or not. While many respect him, it’s clear: he’s not the easiest manager to love.

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