As one of the most recognizable clubs in European football, AC Milan has not been the pride of Italian football for a long time. At the beginning of the century, the Rossoneri were successful in both domestic leagues and European competitions, attracting some of the world's best players to the San Siro. In addition to signing some of the world's best players over the years, Milan have sold some top talent for huge transfer fees.
10. Paqueta (€20 million, Lyon, 2020)
Lucas Paqueta, touted as the next Kaca, joined Milan at a high price from Flamengo in January 2019. The Brazilian was 21 at the time and expectations were too high for him because he had only been in San Siro for one and a half seasons, scoring just one league goal in 37 games. Lyon offered Paqueta a new chance last summer, leaving Milan for 20 million euros, giving him a new lease of life, scoring nine goals and five assists in 30 games in his first season.
9. Balotelli (€20 million, Liverpool, 2014)
Balotelli had the best season of his career when he signed for Liverpool in the summer of 2014. Milan took advantage of Liverpool's desperate need for a striker to replace Luis Suarez, receiving €20 million from the Merseyside club. Having previously returned to England after winning the Premier League title with Manchester City, Balotelli's experience at Anfield was a disaster, scoring one goal and only 16 times in the Premier League. The polarised striker will return to Milan on loan after a season and has never been able to live up to expectations.
8. Patrick Kluivert (€20 million, Barcelona, 1998)
It was by far the oldest deal on the list, and Patrick Kluivert's €20 million transfer from Milan to Barcelona was a very lucrative deal at the time. The Dutchman spent only one year at Milan, a disappointing season with just six Serie A goals in 27 games. He quickly improved in Barcelona and scored 91 goals in La Liga, but won just one trophy at Camp Nou – the league title of his first season. As legends of Football in the Netherlands and around the world, Milan may wonder what would have happened if the deal hadn't been completed prematurely.
7. Suso (€21 million, Seville, 2020)
After struggling to get into Liverpool in the early 1910s, Suso joined Milan in January 2015 for near-zero. Suso was 22 years old at the time and was loaned to Genoa 12 months later before moving into Milan's starting line-up as a key player for three seasons. But the 2019-20 season started disappointingly, with him being loaned to Sevilla, where he will win a Europa League title before completing a permanent transfer. Considering that the Spaniards scored just seven goals in 34 la Liga games last season, the deal so far seems like a good deal for Milan, especially given their huge profits.
6. Ibrahimović (€24 million, Paris Saint-Germain, 2012)
Ibrahimovic, who won the league with Inter milan twice, joined Milan from Barcelona in 2010 and a year later turned the loan format into a permanent transfer. The Swedish superstar won the league title in the club's first season and then scored 28 goals in 32 games in his second season, allowing him to move to Paris Saint-Germain as the latter began to build his empire in French football. Zlatan had a great performance in France, scoring 38 goals in his last Ligue 1 season, which made the €21 million Milan received from him look far from enough, especially considering that they had signed him for a total cost of €30 million in the first place. Ibrahimovic returned to San Siro in 2020, scoring 25 goals in 37 Serie A games in the one and a half seasons he returned to the Rossonere.
5. Piyantek (€24 million, Hertha BSBS, 2020)
For a short period of time, Piyantek was one of the most form-effective strikers in European football, creating fear in the Serie A defence. The Polish striker left his home country for Genoa in 2018, where he scored 13 goals in just half a season and moved to Milan immediately during the January transfer window. Piyantek scored nine more league goals after the transfer but soon lost his magic in his second season, scoring just four goals in 18 games. This prompted another transfer in January of that year, a loan to Hertha Berlin, which was transferred to permanent in the summer of 2020.
4. Bonucci (€35 million, Juventus, 2018)
In 2017, Bonucci moved to Milan for a staggering €42 million, one of the most bizarre transfer experiences in recent years. Bonucci forged an incredible defensive partnership with Chiellini and Barzagli, but he turned his back on the old woman and was immediately named captain of Milan. Bonucci played 35 Serie A games, scoring a goal against Juve, but his time at Milan was short and ill-fated. The centre-back submitted a transfer application the following summer and returned to Juventus, losing 7 million euros on one entry and one exit, much to the embarrassment of Milan.
3. Thiago Silva (€42 million, Paris Saint-Germain, 2012)
In the same window where Ibrahimovic was bought by Paris Saint-Germain, Thiago Silva made the same move for almost twice as much, coming to the Parc des Princes for a transfer fee of 42 million euros. The Brazilian wore the rossoner's captain's armband but left the club to continue his journey when he reached his peak, becoming one of the best centre-backs in Paris Saint-Germain's history. Just two weeks before the transfer, Silva signed a five-year contract extension at Milan and said he wanted to stay at the club. However, Ancelotti eventually raided his former club, Silva, who spent eight years in Paris before moving freely to Chelsea in 2020.
2. Shevchenko (€44 million, Chelsea, 2006)
Ukrainian legend Shevchenko was still in the best shape of his time in Milan when he joined Premier League champions Chelsea for 44 million euros in 2006. Milan signed Shevchenko from the Teenager Dynamo Kiev club at the age of 23, and the €24 million fee shows the hope he showed earlier in his career. Shevchenko became one of the best Number 9 players in the world while in San Siro, but never did so at Chelsea, scoring just nine goals in 48 games. The Ukrainian returned to Milan on a one-season loan contract, but failed to score in 18 games before he returned to Dynamo Kiev to end his career.
1. Kaka (€67 million, Real Madrid, 2009)
Real Madrid spent money like crazy in the summer of 2009, signing Ronaldo, Alonso, Benzema and Kaka. The latter came to the Bernabeu for 67 million euros, and after six brilliant years in Milan, it was a particularly large transfer fee at the time. Kaka won the league and Champions League in Milan and the Ballon d'Or in 2007 while in Milan. Although Kaka returned for a season after four years, Milan have struggled with just one league title since he left Madrid and have not been able to play in the Champions League for many years since that deal.