Football might be a game of passion, but in Milan, it’s also a game of big money.
Over the years, AC Milan has seen some incredible transfer deals that reshaped both the club’s future and the careers of its stars, including homegrown heroes and international sensations.
Yet these sales are more than just numbers on a balance sheet, they’re stories of glory, heartbreak, and second chances.
In this countdown, we’ll look at the top five most expensive sales in Milan’s history, and how each player’s journey has unfolded after they left the San Siro.
Thiago Silva - €42 million
Thiago Silva’s move from AC Milan to Paris Saint-Germain in 2012 made global headlines.
The Brazilian defender arrived for a reported €42 million, making him the most expensive defender at the time. At Milan, Silva had become a rock at the back, helping the team lift the Serie A title in 2010-11 and earning a reputation as one of the most reliable defenders in the world.
At PSG, Silva immediately stepped into a leadership role. He captained the team that would go on to dominate French football for years, winning multiple Ligue 1 titles and became a symbol of PSG’s rise to the European elite.
His biggest assets were his calm presence, tactical intelligence, and ability to read the game that made him invaluable, even during high-pressure Champions League nights.
Later in his career, Silva joined Chelsea on a free transfer, where he added the Champions League trophy to his glittering CV in 2021 and continued playing at the highest level into his late 30s.
Andriy Shevchenko - €43.9 million
When Andriy Shevchenko swapped AC Milan for Chelsea in 2006 for €43.9 million, the football world held its breath. He wasn’t just a good striker, he was the striker.
He was the 2004 Ballon d’Or winner who tore up the Serie A and fired Milan to glory at home and in Europe. Stamford Bridge seemed like the perfect stage for his next act.
But England never quite got the Sheva Milan fans adored. Injuries clipped his pace, the physical demands of the Premier League took their toll, and despite a few sparks of brilliance, he never found the same devastating rhythm.
Two seasons later, he was back in red and black on loan, before eventually closing his career at Dynamo Kyiv, the club where it all began.
His Chelsea years certainly underwhelmed, but Shevchenko’s Milan legacy is bulletproof. The Rossoneri faithful still remember him as the ice-cold finisher and the man who led their attack during one of the club’s golden eras.
Tijjani Reijnders - €55 million
Few players rise as quickly as Tijjani Reijnders did. Signed by Milan from AZ Alkmaar in 2023 for €20 million, his value nearly tripled within two years. By the end of his debut season, including 50 appearances, endless running, and a calmness on the ball beyond his years, Reijnders had already convinced Milan fans they’d found a gem.
Of course, the big sharks were circling. In 2025, Manchester City swooped in with €55 million, seeing him as the perfect fit for their star-studded midfield. For Milan, it was bittersweet. Losing a player so soon after his breakout hurts, but the fee spoke volumes about just how good he’d been.
Reijnders may have only worn the Rossoneri shirt briefly, but he left a mark. Fans won’t forget the energy and the way he controlled games on both sides of the pitch. His story at Milan was short, but it was enough to show he belongs to football’s very top table.
Sandro Tonali - €58.9 million
After winning the Serie A and leaving Milan as a champion, Tonali fell from grace shortly after his arrival at Newcastle after becoming embroiled in a betting scandal.
The then 22-year-old was banned from playing football for 12 months after breaking strict sports betting rules in the eyes of the Italian and English football associations. The ban doesn’t apply to all gambling. Tonali could have checked out the best mobile casinos on the coach to away games, for example, but wagering on another football game is a huge no-no.
Now 25, the midfielder has recovered from this career setback to become a pivotal figure in the Newcastle starting eleven. He helped the club to win their first major trophy in 70 years back in March, playing a key role in the League Cup final win over eventual English champions Liverpool.
Boss Eddie Howe regards him as part of the team’s spine and, as he enters his prime at the age of 25, he’s central to any hopes that the Magpies have of further success over the coming years.
Kakà - €67 million
Kaká’s move from AC Milan to Real Madrid in the summer of 2009 was one of football’s biggest headlines. The Brazilian playmaker arrived for a staggering €67 million, making him the second-most expensive transfer in history at the time. Expectations were sky-high. Fans imagined Kaká dazzling at the Bernabéu, recreating the magic that had earned him the Ballon d’Or just a year earlier.
But reality proved harsh. Persistent injuries dogged Kaká from the start, meaning he could never really get into a rhythm for the Madrid giants. He still produced flashes of his signature brilliance, however, including a glorious 25-yard piledriver at the Madrid derby.
Also, let’s not forget the fact that he notched up 49 goals and assists in 85 league games, more than one in two games. His move wasn’t the disaster people make it out to be.
After four seasons, Kaká returned to AC Milan in 2013 before ending his career with Orlando City SC in MLS.
His Real Madrid years are remembered as a mix of unrealised potential and occasional magic, and that reminds us that even football's most elegant stars can be humbled by injuries.
