Sun. Nov 16th, 2025

Italy’s Treacherous Path to the 2026 World Cup: A Playoff Predicament

Mateo Retegui of Italy celebrates scoring

The Italian national football team, a perennial powerhouse, finds itself in a familiar, yet deeply uncomfortable, position: facing the high-stakes drama of the World Cup playoffs. For a nation that has missed the last two global showpieces, the phrase “the beautiful part starts now” rings with both a desperate hope and a chilling premonition of past failures. The road to the 2026 World Cup in North America is proving to be less a scenic cruise and more a tortuous, obstacle-ridden endurance test.

Gattuso`s Pragmatic Blueprint Takes Shape

Under the helm of coach Gennaro Gattuso, there`s a discernible shift towards what many describe as “normalcy and concreteness.” Gone are perhaps some of the more elaborate tactical philosophies, replaced by a straightforward, results-oriented approach. This pragmatism is particularly evident in his decision to field a double-striker system. It’s a clear acknowledgment of the current squad`s strengths – namely, a robust roster of central forwards like Kean, Retegui, and Esposito – and its current limitations in creative wingers or high-level attacking midfielders. When you don`t have a magician, you focus on the brute force and directness you do possess.

Recent results have been a mixed bag, as is often the case when attempting to rebuild a footballing identity. Dominant victories against lesser opposition, such as a convincing 3-0 against Israel and the dismantling of Estonia, provided some much-needed confidence. However, the stark reality check came in the form of a clear defeat against Norway – the group`s strongest rival, featuring the indomitable Haaland. While beating minnows is “the minimum we could expect,” the true test of this squad`s mettle will undoubtedly come against opponents who can genuinely challenge them.

A Squad of Contradictions: Talent Tempered by Anxiety

The Italian squad possesses an intriguing blend of world-class talent and nagging anxieties. In attack, there`s a renewed sense of optimism. Mateo Retegui, the Italo-Argentine striker, has been particularly impressive, demonstrating a knack for crucial moments – winning and converting a penalty against Israel, then sealing the match with a superb goal. Alongside Moise Kean and the promising Esposito, Italy finally seems to be finding consistent scorers, a welcome relief after years of searching. Indeed, the commentators were quick to anoint Esposito as “the new Vieri,” a comparison that carries both weight and, perhaps, a hint of premature enthusiasm.

Italian National Team in action

Yet, even amidst attacking celebrations, defensive frailties persist. Gianluigi Donnarumma, widely regarded as one of the best goalkeepers in the world, has consistently been called upon to perform heroics. His crucial saves, particularly when the scores were tight against Israel, served as stark reminders that the defensive phase still requires significant refinement. It’s an oddly comforting, yet alarming, reality that Italy often relies on its shot-stopper to bail out the entire backline. One might say, with a touch of irony, that Donnarumma is so good, he makes the defense look… less bad than it sometimes is.

Beyond the immediate concerns, the core of the squad remains strong. Players like Alessandro Bastoni and Riccardo Calafiori are emerging as international-level defenders, while Nicolò Barella and Sandro Tonali continue to be among Europe`s finest midfielders. Complementary talents such as Dimarco, Politano, Di Lorenzo, and Mancini, with youngsters like Buongiorno and Scalvini waiting in the wings, suggest a depth that should theoretically allow Italy to compete. As the article rightly points out, “we are not as great as in many past periods, but not as small as we sometimes like to say (and as results sometimes suggest).”

The Playoff Gauntlet: A History Lesson Awaiting a New Chapter

Any faint hope of direct qualification for the World Cup is now largely theoretical, relying on an improbable slip-up by Norway against Estonia. Realistically, Italy`s destiny lies, once again, in the playoffs. This means a two-stage knockout battle: a semi-final followed by a final, a format that demands perfection and allows absolutely no room for error. The stakes couldn`t be higher, especially given the agonizing memories of missing the 2018 and 2022 World Cups via this very route.

The draw for these playoffs will be crucial. Italy faces the potential “ghosts of the past” in the semi-finals, with familiar adversaries like Sweden or North Macedonia looming as possible opponents. Should they navigate that hurdle, the final could see them traveling to challenging away venues against teams like Scotland, Slovakia, Albania, or Hungary. These are not pushover teams; they are often gritty, well-organized, and fiercely passionate, especially on home soil. Winning there will be anything but easy.

A Fragile Optimism for a Footballing Nation

Despite the “heavy disappointments” of recent years (with the glorious Euro 2021 triumph standing out as a notable exception), there`s a foundation of optimism that persists. This isn`t blind faith, but rather a conviction in the underlying quality of Italian footballers. Gattuso`s pragmatic leadership, focused on making “simple, logical choices,” might just be the steady hand required. The twin-striker formation, for instance, isn`t revolutionary, but it`s a logical deployment of available resources to maximize goal-scoring opportunities.

So, as the Azzurri prepare for yet another playoff journey, the question remains: Will common sense and the inherent grit of Italian football be enough to overcome the psychological burden of past failures and the very real challenges ahead? Or will the “tortuous path” lead to another chapter of heartbreak? America awaits, but Italy must first prove it deserves to be there. The nation holds its breath, hoping this time, the “beautiful part” truly lives up to its name.

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By Marcus Blakely

Based in Bristol, Marcus has been covering sports news for over 15 years. His insightful analysis of rugby and cricket has earned him respect across the industry. When not attending matches or conducting interviews, Marcus enjoys hiking in the Cotswolds and brewing craft beer at home.

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