AC Milan’s 25 most expensive transfers of all time

Cameron Smith

• Updated: 23 Oct 2025 05:43 CDT
• 10 min read

News

While they may not be challenging for Champions League titles like they used to, AC Milan remain one of the most prestigious and well-supported clubs in European football.

Furthermore, after years of stagnation and poor signings, Milan have now stabilised and are once again one of the best teams in Italian football.

Despite their struggles last season which saw them fail to qualify for European football, they are showing signs of recovery in 2025/26.

Below, we run through the 25 most expensive AC Milan signings in history.

25-16

25. Hakan Calhanoglu - €23m (from Bayer Leverkusen, 2017)

Calhanoglu spent four average years at Milan before infuriating fans by joining rivals Inter on a free transfer.

At Inter he became a big star, winning the Scudetto and reaching two Champions League finals.

24. Andriy Shevchenko - €24m (from Dynamo Kiev, 1999)

One of Milan’s greatest ever strikers, Shevchenko scored 173 goals in seven glorious years before leaving for Chelsea in 2006.

He scored the winning penalty in their 2003 Champions League final win on penalties over Juventus.

23. Alexandre Pato - €24m (from Internacional, 2008)

Pato joined Milan as the most exciting teenage talent in Brazilian football.

He started well and for a few years he looked like he could develop into a big star. But he never fulfilled his potential and left in 2013 to return to Brazil.

22. Andrea Conti - €24m (from Atalanta, 2017)

Milan signed one of Italy’s most promising youngsters from Atalanta but Conti’s time at San Siro was a nightmare.

He tore his ACL weeks after joining and his career never recovered. He retired at the age of just 31 after years of problems.

21. Zlatan Ibrahimovic - €24m (from Barcelona, 2011)

Zlatan was Milan’s key man as they won a first Scudetto in seven years in 2011.

He only spent two years at Milan as he was sold for financial reasons to PSG but they were two goal-filled years.

20. Ronaldinho - €24m (from Barcelona, 2008)

Silvio Berlusconi was in love with Ronaldinho when he was at Barcelona and brought him to Milan in 2008.

Although he was past his Ballon d’Or best, he was still exciting to watch but he left six months before their 2011 Scudetto success.

19. Tijani Reijnders - €24.8m (from AZ, 2023)

Reijnders enjoyed two brief but individually successful seasons at Milan.

He developed into an exciting all-round midfielder before a big money move to Manchester City.

18. Alessio Romagnoli €25m (from Roma, 2015)

Milan spent heavily on Romagnoli in 2015, thinking they had bought Italy’s next top centre back.

He never reached the heights expected but he was serviceable and lifted the Scudetto as squad captain in 2022.

17. Alberto Gilardino - €25m (from Parma, 2005)

Big things were expected of Gilardino when he joined Milan in the summer of 2005.

But Gilardino never really won over coach Carlo Ancelotti, despite a decent goal record.

16. Alessandro Nesta - €31m (from Lazio, 2002)

Nesta will be remembered as one of the greatest Italian defenders of all time and one of the best of the 21st century, full stop.

In 10 glorious years at Milan, he won two Scudetti and two Champions League titles. A class act.

15-11

15. Franck Kessie - €32m (from Atalanta, 2019)

Franck Kessie emerged as a powerful young midfielder at Atalanta, convincing Milan to sign him in 2019.

After a slow start, he would play a pivotal role in their 2022 Scudetto success alongside Sandro Tonali in midfield. He left Milan for Barcelona on a free transfer that summer.

14. Santiago Gimenez - €32m (from Feyenoord, 2025)

Milan spent heavily midway through the 2024-25 in an attempt to rescue what would end up being one of the worst seasons in their history.

Gimenez was signed in January 2025 but struggled badly as Milan finished eighth. There is still time for him to come good.

13. Carlos Bacca - €33m (from Sevilla, 2015)

Milan made a string of terrible striker signings at around the time they bought Bacca in 2015.

The Colombian had been one of the best number nines in La Liga but he was nowhere good enough for a Milan side that was going through a crisis at that time.

12. Krzysztof Piatek - €35m (from Genoa, 2019)

Piatek was hastily signed midway through the 2018-19 season after a stunning first half to the campaign with Genoa.

He started well at Milan, too, but then soon fell away and proved to be a disastrous signing. He was sold to Hertha Berlin after less than two seasons.

11. Fikayo Tomori - €35.3m (from Chelsea, 2021)

AC Milan signed Tomori from Chelsea in January 2021 and he immediately impressed.

In his first full season he helped the Rossoneri win a first Scudetto in 11 years.

10-1

10. Ardon Jashari - €33.3m (from Club Brugge, 2025)

Ardon Jashari joined this list when he completed a €33.3m move from Club Brugge to Milan in the summer of 2025.

The Switzerland midfielder established himself as a top young prospect during his sole season at Club Brugge and Milan fought off significant competition for his signature to land him ahead of the 2025-26 season.

In total, Jashari racked up 52 first-team appearances across a one-year spell at Brugge, having joined the Belgian side from boyhood club FC Luzern in 2024.

Current ETV

Ardon Jashari 

DM, M (C)

Milan

Ardon Jashari 

DM, M (C)

Milan

€38.3M

ETV Range

€34.5M - €42.2M

View full profile

9. Filippo Inzaghi - €36.2m (from Juventus, 2001)

Filippo Inzaghi seems to divide opinion among Italian football fans, but one thing that was undisputed was his knack for the big occasion.

His brace in the 2007 Champions League final would have been enough to pay back his €36.2m transfer fee, let alone the rest of a fabulous career at San Siro.

Inzaghi scored 126 Serie A goals in 300 games for Milan with a further 29 in the Champions League, before retiring in 2012 with three league titles and two Champions Leagues tucked under his arm.

8. Christopher Nkunku - €37m (from Chelsea, 2025)

When Chelsea signed Christopher Nkunku from RB Leipzig in 2023, it was seen as a major coup, and the Frenchman was expected to guide the Blues back towards the top of the Premier League.

However, injury issues curtailed his career at Stamford Bridge and he remained behind Cole Palmer in the pecking order throughout his two-year spell in west London.

Following the signing of Joao Pedro from Brighton & Hove Albion, Nkunku was heavily linked with a Chelsea exit, and Milan were able to finalise a €37m deal in August 2025.

7. Charles De Ketelaere - €37.5m (from Club Brugge, 2022)

After winning the 2022 Scudetto on a dramatic final day of the season, Milan set about improving their squad ahead of the next campaign, and their marquee signing of the summer was wonderkid Charles De Ketelaere.

The attacking midfielder was compared to former Milan stars Kaka and Rivaldo before arriving, but his first season was extremely disappointing and he failed to score in 32 Serie A appearances.

De Ketelaere was loaned to Atalanta for the 2023-24 campaign and, after relaunching his career there, he made the move permanent in the summer of 2024.

6. Mattia Caldara - €37.7m (from Juventus, 2017)

When Leonardo Bonucci made it clear that he wanted to re-join Juventus after just one year away, Milan allowed him to return to Turin, but they demanded Mattia Caldara be included in the deal.

Caldara duly made his way to San Siro, with Milan paying €37.7m for the Italian after an impressive season on loan at Atalanta.

However, a lack of form and injuries meant that Caldara was unable to settle at Milan and he was loaned to Atalanta (2020-21), Venezia (2021-22) and Spezia (2022-23) after 18 months of underwhelming form at San Siro. Caldara was finally released in 2024 upon the expiration of his contract.

5. Andre Silva - €38m (from Porto, 2017)

The second-most expensive player in new owner Yonghong Li’s extravagant 2017 spending spree was young Porto striker Andre Silva.

At the time, Silva had a burgeoning reputation following his goal-scoring exploits at Porto, however he was unable to replicate that form in Serie A and he was only able to score 10 goals in 41 games for Milan.

Silva joined Sevilla on loan a year later, followed by a subsequent loan to Eintracht Frankfurt, who purchased him permanently for just €3m in 2020.

4. Lucas Paqueta - €38.4m (from Flamengo, 2019)

Milan attempted to replicate the huge success they had bringing Kaka to Europe from Brazil at a young age by acquiring wonderkid Lucas Paqueta from Flamengo in January 2019.

Much like Kaka, Paqueta had built up a brilliant reputation during his time in Brazil, but the pressure to live up to the Milan legend ultimately proved too much, and he managed just one goal in 44 appearances for the San Siro outfit.

Paqueta was then sold to Lyon and after excelling in France, West Ham spent €43m to bring him to the Premier League in 2022.

3. Rui Costa - €41.3m (from Fiorentina, 2001)

When Fiorentina head coach Fatih Terim was appointed Milan head coach ahead of the 2001-02 season, one of his first orders of business was to bring Viola playmaker Rui Costa with him.

‘The Maestro’ would become Milan’s most expensive transfer at the time after a €41.3m deal was agreed between the two clubs.

Costa 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 San Siro, before eventually losing his place to the aforementioned Kaka.

2. Leonardo Bonucci - €42m (from Juventus, 2017)

In what was certainly viewed as a bizarre transfer at the time, Leonardo Bonucci left all-conquering Juventus in the summer of 2017 to join their rivals, Milan.

Having formed one of the most formidable backlines in history alongside Gianluigi Buffon, Giorgio Chiellini and Andrea Barzagli, Bonucci made the decision to jump ship after seeing his relationship sour with head coach Massimiliano Allegri.

But, after failing to find his best form at Milan, Bonucci eventually returned to Juventus after just one year away.

Current ETV

Rafael Leão

F, M (L)

Milan

Rafael Leão

F, M (L)

Milan

€71.9M

ETV Range

€64.7M - €79.1M

View full profile

1. Rafael Leao - €49.5m (from Lille, 2019)

The most expensive AC Milan signing of all time is Portuguese attacker Rafael Leao. The speedy winger had impressed at Ligue 1 side Lille, which convinced Milan to agree a deal worth nearly €50m.

After playing a bit-part role during his debut season, Leao soon emerged as a key player at San Siro and he eventually led Milan to the 2022 Serie A title by scoring 11 and assisting 10 in 34 league games.

Despite annual links with a Premier League transfer, Leao has now made over 250 appearances for Milan.

The 10 most expensive Milan signings of all time

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