Kluivert continued his career at the Italian club AC Milan. Here, he reunited with Edgar Davids and Michael Reiziger, who had left Ajax the previous season. Winston Bogarde also joined the red and black team. Besides having some familiar faces around, there was another reason for Kluivert’s choice. His childhood idols, Marco van Basten and Frank Rijkaard, had achieved their greatest successes at the Italian powerhouse, and Kluivert wanted to follow in their footsteps. However, things took a turn for the worse for the 21-year-old striker in Serie A.
He had a promising start, scoring against Juventus in the Trofeo Berlusconi competition. But in the league, Kluivert struggled. It was a tough season for Milan, who ultimately finished in tenth place. Kluivert couldn’t live up to the high expectations of the critical fans who wanted to see more goals. As the goals dried up, he faced harsh criticism from the crowd. He was booed in almost every game and even earned nicknames like “Il Bergkamp nero” (the black Bergkamp, referring to Dennis Bergkamp’s less successful period at Inter Milan). Coach Fabio Capello also showed little confidence in him. He quickly found himself on the bench, and midway through the season, Maurizio Ganz was brought in to strengthen the attack. Kluivert managed to score six goals in the league, with only George Weah scoring more for AC Milan that season. In the cup competition, Kluivert contributed with three goals to reach the final. However, he wasn’t selected to play in the final match, which SS Lazio won while he watched from the sidelines.
After the World Cup in France, things took a different turn. Milan had parted ways with Capello, and Zaccheroni took over as the coach. During the preparations for the new season, it seemed like Kluivert might get a second chance, even with the arrival of the new star signing, Oliver Bierhoff. Several big clubs, including Manchester United and Arsenal, were also interested in signing him.
However, it appeared that Kluivert would start the next season with AC Milan. But on the last day of the transfer window, Louis van Gaal personally flew to Milan to bring Kluivert to Barcelona. Milan received approximately 15 million euros for the striker.