Milan grew up in Friuli, in north-east Italy, and came into the sport as a pursuiter rather than a sprinter. He rode in the Italian quartet that beat Denmark to team pursuit gold at the Tokyo Olympics in a world record 3:42.032, and won a world title in the same event in 2021. He was still on the track in 2024, taking the individual pursuit world championship in Ballerup with a world record of 3:59.153.
His road career started at Bahrain Victorious in 2021. He rode the Giro d'Italia for the first time in 2023, won stage two in a mass sprint, kept finishing near the front of the bunch finishes and left with the maglia ciclamino at the first attempt. He moved to Lidl-Trek for 2024 and came back to the Giro with three stage wins and a second points jersey.
He did not ride the Tour de France until 2025. The race gave up very few clean bunch sprints that year, so Lidl-Trek went after the points classification instead, holding him near the front on flat days and chasing breakaways down. He won two stages and collected intermediate sprints in between. Tadej Pogačar, on his way to the yellow and polka-dot jerseys, was the rival for green until the finish in Paris.
He wins on raw power rather than positioning, opening the sprint from a long way out and holding the speed to the line instead of waiting for a gap to appear. Simone Consonni, who was in the Tokyo pursuit quartet with him, leads him out, with Edward Theuns ahead of that. Quinn Simmons was voted the 2025 Tour's super-teammate for the work he did keeping Milan out of trouble.
He won elsewhere in 2025 as well: a bunch sprint at Tirreno-Adriatico in March, a stage of the Critérium du Dauphiné in June, and Kampioenschap van Vlaanderen in September. Lidl-Trek extended his contract to 2029 in August that year, and tied both lead-out men to the team through 2027.









