Charles De Ketelaere returns to San Siro with a different career behind him. Nearly 50 months after arriving at Milan as the major signing of a title-winning summer, the Belgian is due back at the stadium where expectation quickly became pressure. His path has since taken him through Atalanta, an Europa League triumph, 27 goals across two seasons and a changing role under different coaches, yet the question around his Milan year has never entirely disappeared.
Key takeaways
- Milan signed De Ketelaere from Club Brugge for €32 million, plus €3 million in attainable bonuses and 12.5% of any future profit on a sale.
- He failed to score during his sole season with the Rossoneri and left after one campaign.
- Atalanta later paid €22 million to make his move permanent, after a €3 million initial loan fee.
- The Belgian recorded 27 goals in his first two seasons in Bergamo and helped Atalanta win the Europa League.
- At the 2026 World Cup, he scored twice against the United States and was the only player to find the net against Spain.
A Milan promise that never settled
De Ketelaere’s arrival in 2022 carried the weight of a summer-long pursuit. Paolo Maldini and Ricky Massara had identified him as the principal addition after the Scudetto, holding meetings in Bruges and Lugano as Milan sought to conclude a deal that stretched across the European summer.
At Club Brugge, De Ketelaere had been used in a remarkable range of positions, including at left-back. Milan, however, saw him primarily as an attacking midfielder: a player with imagination, acceleration and an eye for goal. The club’s supporters embraced the idea quickly, with some casting him as a possible successor to Kaká and adapting the familiar Kinder chocolate image around the new Belgian signing.
That symbolism soon became uncomfortable. His first Serie A away match came in Bergamo, against the Atalanta side that would later revive his career, but his adaptation to Milan’s stage was difficult. In the first derby of the season, he lost track of Marcelo Brozovic, who went on to score. Thereafter, confidence became an increasing concern.
There were isolated signs of his ability, but no goal arrived. A glaring missed chance against Monza became one of the defining images of his season, and he did not recover from it. Maldini and Massara would have been prepared to retain him for another year, but the subsequent direction under Giorgio Furlani and Geoffrey Moncada was different: De Ketelaere was moved on after a single season.
The assessment is not simply that Milan bought a poor player. Rather, the role imagined for him did not prove to be the right one, while the environment demanded an immediate response from a player who had previously known only the club from his home city. San Siro was a sharp step up, and he was not ready to meet it.
Bergamo gave him another shape
Gian Piero Gasperini immediately found more production from De Ketelaere. Used further forward, he reached double figures straight away and accumulated 27 goals over two seasons. One of the most telling came against Milan: a forceful header above Theo Hernandez in a league meeting, a finish that suggested a physical authority rarely seen during his Rossoneri spell.
Atalanta’s decision to retain him followed a landmark campaign. The club won the Europa League, with Ademola Lookman central to the final, and then completed De Ketelaere’s permanent transfer for €22 million. Combined with the €3 million loan payment, the operation gave Milan €25 million back for a player whose original deal had cost considerably more.
His development has not been a straight ascent. He has delivered goals in the Champions League, but also endured quieter stretches, and his current start under Maurizio Sarri has been described as complicated. Sarri has used him as a wide player, another indication that the No. 10 role Milan envisaged has not become his natural home.
The World Cup nevertheless added another important chapter. De Ketelaere scored a brace against the United States in the round of 16, and his goal against Spain made him the tournament’s only scorer against the Spanish side. It was further evidence that his ceiling remains substantial, even if consistency and resilience have not always matched his talent.
His return to San Siro therefore does not invite a simple verdict. De Ketelaere is not the explosive, central attacking midfielder Milan hoped might resemble Kaká; he lacks the tight-space dribbling and burst required for that comparison. But he has become a valuable forward with Atalanta, capable of contributing on major European and international occasions. For now, Bergamo has proved the more suitable setting, and that is not a failure for a player whose career has needed time, a new coach and a different responsibility to find its proper direction.
