Carletto’s bittersweet link to the United States and the 2026 World Cup

In the Rose Bowl’s shadow, the 2026 FIFA World Cup’s Round of 16 unfolds this weekend with AC Milan still the best-represented Italian club, fielding seven Rossoneri players. As Brazil and Mexico departed the tournament, the Rossoneri’s presence in the competition remained unmatched among Italian clubs. Seven Milan players are still competing ahead of the Portugal v Spain and United States v Belgium clashes. Yet the exits of Brazil and Mexico carried a personal echo for one of AC Milan’s greatest icons. Carlo Ancelotti, known to Rossoneri fans as Carletto, watched his native Brazil fall in the knockout phase. That outcome held particular resonance because the United States never treated him kindly during his playing days. His only major triumph on American soil came in 1993 when AC Milan lifted the Italian Super Cup in Los Angeles, though he was then part of Arrigo Sacchi’s Italy coaching staff preparing for the 1994 World Cup in the US.

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The 1994 tournament ended with Brazil beating Italy in the Rose Bowl final. By 2003, Ancelotti was AC Milan’s head coach when the Supercoppa Italiana final was played in New York. On that occasion, Juventus defeated the Rossoneri on penalties. Ancelotti’s relationship with the United States stretched beyond competition. During his eight-year tenure as AC Milan’s head coach from 2001 to 2009, he led the club on multiple pre-season tours across the US, facing Chelsea, Manchester United and MLS sides. Those summer trips became a staple of Milan’s preparation.

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Even after leaving the Rossoneri, Ancelotti maintained his transatlantic link. As coach of Chelsea, Bayern Munich and Real Madrid, he returned to the US to face AC Milan in summer friendlies, reinforcing his enduring connection to the country. The 2026 World Cup’s presence in the United States, Canada and Mexico adds another chapter to Ancelotti’s complex American story. From playing disappointment to coaching success and back again, the country remains a stage where his legacy is both celebrated and tested.