As they peered through the smoke from lit flares, fans of the Italian soccer team AC Milan dancing beneath the towering Italian gothic cathedral in the city’s Piazza Duomo may have noticed a tanned 56-year-old Italian American who didn’t quite look like he belonged.

Gerry Cardinale’s dark blue polo stood out amid the red and black striped jerseys the fans of the “rossoneri” wore—if they were wearing shirts at all—to celebrate the team’s title-clinching 3-0 victory against Sassuolo. It was May 2022 and the public announcement had not yet gone out, but Cardinale had just agreed to a $1.2 billion deal to buy the legendary football club.