Prison and shady dealings: what did the 'Libyan curse' do to Italy's legends?

No one embodies the struggles of this generation better than Andrea Pirlo. The maestro who orchestrated Italy's midfield to World Cup glory saw the Azzurri as the chance to rescue his faltering coaching career. When Paolo Maldini and Leonardo arrived last July to lead the rebuild of a lost national team, Pirlo stood out as the preferred and most likely man for the job.

Then it all collapsed. Giovanni Malagò, president of the Italian Football Federation, suddenly dropped his candidacy. The stated reason was Pirlo's extensive commercial ties with Russia, something the institution judged incompatible with the image of the national team at this moment.

The blow did more than deny Pirlo his return to the top. It confirmed the run of failures that has followed him since he hung up his boots. A promising but unfulfilled start at Juventus gave way to lacklustre spells at Turkey's Fatih Karagümrük and Sampdoria, before he landed at United FC in the UAE second division, where he remains under contract to this day. It is a path that never befitted a legend of his stature.

Before Pirlo's illusory fall, there was a real and resounding fall for his midfield team-mate, Gennaro Gattuso. The first coach from the 2006 generation to reach this lofty position, "Rino" arrived in June 2025 with a clear and indivisible mission: lead Italy to the 2026 World Cup and rescue the reputation of Italian football after two consecutive absences from the tournament.

The mission ended in an even greater catastrophe. A shocking failure against Bosnia and Herzegovina left Italy out of the World Cup for the third consecutive time, a humiliating historic first for Italian football. His coaching career began early, back in 2013, and took him through Milan, Napoli, Valencia and Marseille, yet he showed no notable tactical development with the Azzurri and simply repeated the same old mistakes.

Somehow, Gattuso retained his appeal in the Italian coaching market. He quickly found a new lifeline in Serie A by taking charge of Lazio, a fresh attempt to prove that his ferocity as a player could finally translate into success as a coach.

Only two names cut through this bleak scene as genuine exceptions to the curse of the Libyan generation, and the pair will go head to head in the new 2026-2027 season. Fabio Grosso comes first, hero of the Berlin night with his goal against Germany and his decisive spot-kick in the final. 

A fleeting spell of no more than 76 days at Olympique Lyonnais threatened to derail him. Yet Grosso reinvented himself at Sassuolo, dragging them back to Serie A with an exceptional season. Fiorentina rewarded him with a bigger role, and now he must prove his success was no fluke.

Daniele De Rossi is the second name, and he looks the most tactically mature of his peers. His Genoa side finished last season in only sixteenth place, but their performances drew wide praise and showcased modern attacking ideas. 

That experience marked a genuine breakthrough after two faltering starts with SPAL and Roma. Today he ranks among the most promising young coaches in Italy.

The stories of the remaining heroes grow more tangled away from the spotlight. Filippo Inzaghi, the historic goalscorer who dragged Pisa back to the top flight in 2025, surprised everyone. He turned his back on the limelight to take on a fresh challenge in the second division with Palermo, the City Group-owned club chasing an ambitious promotion project.

Waiting there is a former team-mate, Alessandro Nesta, who is trying to rebuild his career once more with Avellino after a full year out of work following his failure at Monza.

Fabio Cannavaro, captain of that golden generation, chose a stranger path in search of glory. Short and unconvincing spells at Dinamo Zagreb, Benevento (17 matches) and Udinese (6 matches) followed stints in China. He then decided to go as far as he possibly could, taking charge of Uzbekistan and leading them to the 2026 World Cup. The adventure ended in disaster: out at the group stage without a single point.

Alberto Gilardino finds himself in much the same boat. Sacked as Pisa boss last February after failing to keep the club up, he is now out of work. His name has been linked with Torino, Verona and Monza as he waits for a chance to play the saviour mid-season.

Massimo Oddo suffered almost the same fate. The most experienced of the group, having coached seven different clubs, he wound up in the fourth division with Milan Futuro. There he came up against another old team-mate, Marco Amelia, the third-choice goalkeeper in 2006, himself sacked as Sondrio coach. The strangest journey of all belongs, without dispute, to Mauro Camoranesi. He has travelled the world, from Mexico and Argentina to Slovenia, Malta and Cyprus, where he currently coaches AEK Larnaca.

Seven champions took a different path. They stayed in the game without ever venturing into coaching. Gianluigi Buffon moved into administrative work at the Italian Federation and earned a sporting director diploma, while Alessandro Del Piero and Luca Toni settled for coaching licences and punditry on television.

Cristian Zaccardo became a players' agent. Francesco Totti set up consultancy firms for clubs, and Simone Perrotta now works in sports policy. The more unusual careers belong to Marco Materazzi, who quit coaching in India to make wine, Angelo Peruzzi, who dabbled briefly in politics, and Gianluca Zambrotta, who swapped television analysis and the padel business to rejoin the Italian Federation in an administrative role in June 2025.

Vincenzo Iaquinta is the tragic exception. He walked away from football entirely after a two-year prison sentence in 2020 tied to mafia-related investigations. His is the darkest ending among the heroes of the Berlin epic.