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AC Milan’s 10 most expensive transfers of all time

Cameron Smith
Rafael Leao, Milan, 2022/23
© ProShots

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

The Rossoneri’s 2022 Scudetto victory confirmed that they are on their way back to becoming a major power again, while they did reach the Champions League semi-final in 2023.

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After years of stagnation and poor signings, Milan have stabilised and are once again one of the best teams in Italy.

Below, FootballTransfers runs through Milan’s 10 most expensive signings ever.

READ MORE: Juventus’ 10 most expensive transfers of all time

READ MORE: Inter’s 10 most expensive transfers of all time

10. Carlos Bacca – €33.3m (from Sevilla, 2015)

Fresh from a match-winning brace in the Europa League final, Carlos Bacca left Sevilla for San Siro in the summer of 2015 with a burgeoning reputation.

Bacca scored 20 goals in his final La Liga season, alongside seven in the Europa League, and his first season at Milan was similarly impressive.

The Colombian hit the ground running with 18 goals in his first campaign at Milan, featuring in every Serie A game.

However, after netting 13 times during his second season, Bacca was loaned to Villarreal before the Spanish side made the deal permanent for €7m in 2018.

9. Krzysztof Piatek – €35m (from Genoa, 2019)

In terms of hitting the ground running, it’s difficult to eclipse Krzysztof Piatek’s first six months in Milan colours.

The Pole was in fine form for Genoa, scoring 13 goals in 19 games, when Milan snapped him up in January 2019, just six months after he had left his native Poland for Italy.

Piatek’s form continued in the Rossoneri shirt. After coming off the bench for his debut against Napoli, Piatek would go on to score in each of the next five games, including two braces.

But, just as quickly as it began, his purple patch came to an end. Piatek scored three goals in the last 10 matches of the season and he was sold to Hertha Berlin for €24m in 2020 and after two loan spells back to Italy, he moved to Turkey on a free transfer in 2023.

8. 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.

It was an expensive deal at the time, but Super Pippo wrote his name into club folklore and has been one of the most successful transfers in Milan’s history to date.

7. Charles De Ketelaere – €36.5m (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.

Charles De Ketelaere, Milan
© ProShots – Charles De Ketelaere, Milan

Their marquee signing of the summer was wonderkid Charles De Ketelaere, who was tipped to be the next big star of Belgian football.

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

De Ketelaere was loaned to Fiorentina for the 2023-24 season and, after relaunching his career there, is likely to make 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 demanded Matta Caldara be included in the deal.

Ultimately, Caldara made his way to San Siro, with Milan paying €37.7m for the Italian, while they earned €35m from Bonucci’s departure.

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 is still on Milan’s books as of 2023-24.

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 growing reputation following his goal-scoring exploits for the Porto youth sides and their first-team. However, he was unable to replicate that form in Serie A.

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.

Lucas Paqueta joined West Ham in 2022
© ProShots – Lucas Paqueta joined West Ham in 2022

Much like Kaka, Paqueta had built up a brilliant reputation during his time in Brazil, with his close control and flamboyancy catching the eye.

The pressure to be the next Kaka ultimately proved too much for the midfielder, however, and he managed just one goal in 44 Milan appearances before being sold to Lyon.

Paqueta excelled in France and convinced West Ham to spend €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 a young Brazilian named Kaka.

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

In what was certainly viewed as a slightly bizarre transfer at the time, Leonardo Bonucci left all-conquering Juventus in the summer of 2017 for 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.

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

The most expensive signing in Milan history 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.

Rafael Leao, Milan
© ProShots – Rafael Leao, Milan

Leao was a bit-part player during his first campaign at San Siro, but still managed to notch six league goals in an encouraging debut season.

He then went from strength-to-strength, culminating in leading Milan to the 2022 Serie A title by scoring 11 and assisting 10 in 34 league games. He backed that up with 16 goals and 15 assists in 2022-23 as Milan reached the Champions League semi-finals and finished fourth in the Italian top flight.

He has been tipped for a big-money exit in the summer of 2024 after a somewhat underwhelming 2023-24 season.

The 10 most expensive Milan signings of all time

Player From Fee Year
1. Rafael Leao Lille €49.5m 2019
2. Leonardo Bonucci Juventus €42m 2017
3. Rui Costa Fiorentina €41.3m 2001
4. Lucas Paqueta Flamengo €38.4m 2019
5. Andre Silva Porto €38m 2017
6. Mattia Caldara Juventus €37.7m 2018
7. Charles De Ketelaere Club Brugge €36.5m 2022
8. Filippo Inzaghi Juventus €36.2m 2001
9. Krzysztof Piatek Genoa €35m 2019
10. Carlos Bacca Sevilla €33.3m 2015

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