AC Milan have endured a disappointing last decade on the pitch due to poor recruitment and management, however, they still retain their status as one of the most decorated and most followed clubs across Europe.
The Rossoneri are not known to splash huge sums in the transfer market unlike many of the other top European clubs, even in this era of obscene inflation. Nonetheless, they have managed to enjoy some recent successes and are once again, one of the best teams in Italy.
Soccernet.football takes a look at the ten most expensive signings in AC Milan’s rich history.
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10. Fikayo Tomori – €34.4m (2021)
AC Milan signed Tomori from Chelsea on an initial six-month loan before making the transfer permanent for €34.4m in 2021. The English defender quickly established himself as a key figure in Milan’s backline and his impact was immediate, helping Milan secure a top-four finish and a return to the Champions League. Tomori’s partnership with Simon Kjær was also instrumental in the Rossoneri’s 2022 Serie A title win, their first in 11 years.
9. Krzysztof Piątek – €35m (2019)
Milan signed the Polish striker in January 2019, just six months after he joined Genoa. Piątek came off the bench for his debut against Napoli and scored in each of his next five games, including two braces. However, his hot streak came to an end as quickly as it began as the Pole managed just three goals in the final 10 matches of the season before being sold to Hertha Berlin for €24 million in 2020. Following two loan spells back in Italy, he moved to Turkey on a free transfer in 2023.
8. Filippo Inzaghi – €36.15m (2001)
Inzaghi joined from Juventus in 2001 and netted 126 Serie A goals in 300 appearances for the Rossoneri, along with 29 more in the Champions League, before retiring in 2012 with three league titles and two Champions League trophies to his name. Although the deal was costly at the time, The Italian certainly etched his name into the club’s history, becoming one of Milan’s most successful transfers to date.
7. Charles De Ketelaere – €36.5m (2022)
Following their 2021/2022 Serie A triumph, Milan signed the highly rated Belgian youngster from Club Brugge. De Ketelaere drew comparisons to former Milan legends Kaka and Rivaldo before his arrival, but his first season was a major letdown as he failed to score in 32 Serie A appearances. The Rossoneri loaned the Belgian international to Atalanta for the 2023/2024 season, and after revitalized his career. He is expected to make the move permanent this summer.
6. Mattia Caldara – €37.74m (2017)
Caldara arrived at the San Siro from Juventus in 2017 while Bonucci made a U-turn and re-joined the Old Lady after one season with the Rossoneri. Caldara saw his early years in Milan plagued by injuries and poor form with the Italian unable to settle at the San Siro. He spent the 2020/2021, 2021/2022 and 3022/2023 seasons on loan at Atalanta, Venezia and Spezia respectively. Milan are yet to reap the gains of their investment seven years later.
5. Andre Silva – €38m (2017)
At the time Milan signed him, the Portuguese forward had a growing reputation following his goal-scoring exploits for the Porto youth sides and their first-team. However, he was unable to replicate that form for the Rossoneri in Serie A. Silva joined Sevilla on loan a year later, followed by a subsequent loan to Eintracht Frankfurt, who eventually purchased him permanently for just €3m in 2020.
4. Lucas Paqueta – €38.4m (2019)
In January 2019, Milan sought to replicate the tremendous success they had with Kaka by bringing another young Brazilian talent to Europe as they signed Paqueta from Flamengo. The weight of expectations to become the next Kaka ultimately overwhelmed the Brazilian, who managed just one goal in 44 appearances for the Rossoneri before being sold to Lyon. Paqueta thrived in France, eventually persuading West Ham to spend €43 million to bring him to the Premier League in 2022.
3. Rui Costa – €41.32m (2001)
Costa became the Rossoneri’s most expensive transfer at the time after a €41.32m deal was agreed between Milan and Fiorentina. The Portuguese subsequently became Milan’s main creative force and helped the club to one Champions League title, one Serie A title and one Coppa Italia during his spell at the San Siro, before eventually losing his place to a young Brazilian named Kaka.
2. Leonardo Bonucci – €42m (2017)
Bonucci had been part of one of the most formidable defensive units in history at Juventus alongside Gianluigi Buffon, Giorgio Chiellini, and Andrea Barzagli, but tensions with head coach Massimiliano Allegri led to his departure in the summer of 2017. The Italy international joined AC Milan in a €42m deal, however, after struggling to settle at Milan, Bonucci returned to Juventus just one year later.
1. Rafael Leao – €49.5m (2019)
The exciting Portuguese winger is AC Milan’s most expensive signing till date. After playing a limited role during his first season at San Siro, he went on to establish himself in Milan’s front line as they won the 2022 Serie A title with 11 goals and 10 assists in 34 league matches. He followed that up with 16 goals and 15 assists in 2022/2023, helping Milan reach the Champions League semi-finals and secure a fourth-place finish in Serie A.
