For years, European soccer has been the fulcrum of the sport’s largest financial swings. The continent is where football’s highest transfers take place, as eyeball-boggling sums are shelled out to secure the services of world-class players. But among the big spenders, A.C. Milan has long adopted a more conservative line of attack, at least in comparison with competing teams like Juventus, which spent more than €1 billion from 2012 to 2022. But when Milan goes to spend, it is, generally, to chase after transformative talents.
Here are the most valuable football players AC Milan has ever signed and what stories their arrival tells about risk, reward, and long-term value.
Who are the most valuable players AC Milan has signed in its history?
Legends like Maldini, Van Basten, Baresi, and Kaka helped build Milan’s legacy. Some were homegrown icons; others arrived for modest fees and left a massive legacy. Then there are those whose names are tied to staggering transfer costs, the most valuable players, at least in economic terms.
1) Rafael Leao:
No Milan signing has cost more than Rafael Leão. Acquired from Lille in 2019 for nearly 50 million euros in total, the Portuguese winger has since become the heartbeat of Milan’s attack. Blistering pace, silky dribbling, and a knack for game-breaking moments have made him a fan favorite, and a nightmare for fullbacks.
His breakthrough came during the 2021–22 season, when he was instrumental in delivering Milan’s first Scudetto in 11 years. Eleven goals and ten assists in the league alone speak volumes. Though his form dipped slightly last season, Leão has more than justified his price tag. In today’s market, he’s not only Milan’s costliest transfer but arguably one of the most valuable football players in the Serie A.
2) Leonardo Bonucci:
When Milan signed Bonucci from Juventus in 2017 for €42 million, expectations soared. The veteran defender arrived with experience, leadership, and a winning pedigree. He was immediately handed the captain's armband and positioned as the cornerstone of a new era. On paper, it made sense.
In practice? Not so much. Bonucci struggled to find his rhythm at San Siro. His lone season in red and black was underwhelming, marked by inconsistent performances and a quick return to Turin. A classic case of a big-name signing that never fit, the price didn’t match the value.
3) Rui Costa:
A maestro in midfield, Rui Costa joined Milan from Fiorentina in 2001 for €41.3 million, a massive fee at the time. Brought in at the request of coach Fatih Terim, Rui Costa became Milan’s creative engine.
During his five seasons with the club, he won everything: Serie A, Coppa Italia, Champions League, and UEFA Super Cup. Unlike flashier players, his impact was subtle but crucial. While not always mentioned among the most valuable football players by cost alone, Rui Costa’s contributions remain priceless in Milan’s modern history.
4) Lucas Paquetà:
In 2019, Milan tried to recreate the Kaka formula, Brazilian flair, signed young, big potential. Lucas Paquetá arrived from Flamengo for €38.4 million. Technically gifted and exciting in Brazil, he was tipped as the next big thing.
But pressure is a tricky opponent. Paquetá never found his footing in Italy, scoring just once in 44 appearances before being shipped off to Lyon. The move reflected a broader issue for Milan at the time: spending big without the right support system around the player.
5) André Silva:
Another costly experiment. Silva joined from Porto in 2017 for €38 million. Hailed for his instincts in front of the goal, Milan hoped he would be their long-term striker.
He scored eight goals in the Europa League but only found the net twice in Serie A. The chemistry just wasn’t there. One season in, and he was loaned to Sevilla. As with Paquetá, the gamble didn’t pay off.
Are the most valuable players always the most expensive signings?
Not at all. In fact, some of Milan’s most valuable players didn’t break the bank. One of the best examples is Andriy Shevchenko. Signed from Dynamo Kyiv in 1999 for $25 million, a huge sum at the time, his name barely cracks Milan’s top 10 most expensive signings today. And yet, he went on to score 175 goals in 296 appearances, becoming a Ballon d’Or winner and club legend.
Then there’s Paolo Maldini, perhaps the most valuable football player in the world, at least for Milan. Cost to the club? Zero. He rose through the youth system and played over 900 matches in Rossoneri colors. No transfer fee can capture his legacy.
What this means for football today?
In an era of player prop bets, inflated wages, and skyrocketing transfer fees, clubs are under pressure not only to buy the right talent but to prove value. That’s why soccer player props, a growing trend in betting markets, often center around expected goals, assists, or minutes played. It’s also why clubs like Milan must balance hype with long-term impact.
Ultimately, the football highest transfers may grab headlines, but value lies in what happens after the deal is done.
