From European glory to relegation battles—Lorenzo Insigne's career has taken a dramatic turn that few could have predicted. The Italian winger was a key starter for the national team when they lifted the UEFA Euro 2020 trophy, and he followed that triumph with an impressive 23 goal contributions in a single season for SSC Napoli, establishing himself as a constant threat in Serie A.

At the peak of his powers, Insigne made a decision that would change everything: he became the highest-paid player in Major League Soccer—until Lionel Messi's arrival—by signing with Toronto FC. From that moment, his career trajectory shifted sharply downward.

The numbers alone don't tell the full story of Insigne's time in Canada. Brought in by Bill Manning as the face of a "new era" for Toronto FC, he instead became a symbol of the club's sporting collapse. His partnership with fellow Serie A import Federico Bernardeschi was marked by disappointing performances on the pitch and controversy off it. According to multiple Canadian reports, the two Italians were allegedly involved in behind-the-scenes efforts to push for coach Bob Bradley's dismissal.

With Insigne in the squad, Toronto transformed into one of MLS's weakest sides, and he never managed to guide the club into the playoffs. His relationship with fans deteriorated further when he reportedly insulted supporters while watching a match from the executive box.

Despite his enormous salary, Insigne remained in Canada until 2025, when he finally agreed to terminate his contract. After this disappointing chapter, he made what he called a decision "from the heart" and signed for Pescara—the club where he first made his mark during the 2011/12 season. Back then, he scored 20 goals alongside Ciro Immobile and Marco Verratti to secure promotion to Serie A before moving to Napoli.

But this "homecoming" quickly turned sour. Although Insigne arrived in January, he didn't start receiving regular playing time until March. His numbers were respectable—five goals and three assists—but the fairy tale ending never materialized.