Updated: 8 October 2026

Between the 2023/24 and 2025/26 seasons, AC Milan went through three consecutive transfer campaigns, bringing in established internationals, promising young players and several short-term solutions.

This board follows 32 of those arrivals, including permanent signings, free transfers and loans. Some became important first-team players. Others moved on after a single season, while several expensive signings are now trying to rebuild their careers elsewhere.

The question is simple: what happened to Milan's €426 million investment?

The numbers

These figures cover the 32 players on this board rather than every transaction completed by AC Milan during the period. Loan fees paid are included in expenditure; loan income, salaries, agent commissions and conditional future transfer payments are excluded from the purchase-versus-sale comparison.

2023/24: A new midfield and attack

Milan made substantial changes during the summer of 2023, investing in midfielders, wide attackers and younger prospects.

Total investment: €131.18m across 11 players.

Reijnders eventually became one of the most significant financial successes of this group, moving to Manchester City for €54.9 million in 2025.

Okafor, meanwhile, was sold to Leeds United for €19 million. Pellegrino, Romero and Sportiello also departed on permanent transfers.

Pulisic and Loftus-Cheek remained part of Milan's first-team setup into the 2026/27 campaign, alongside Musah, Chukwueze and Filippo Terracciano.

The 2023 window offers an interesting contrast: a profitable sale in Reijnders, alongside players whose time in Milan followed very different paths.

2024/25: Another €138 million committed

The following season brought another significant round of investment, including an expensive new striker, defensive reinforcements and a series of winter transfers.

Total investment: €138.30m across 11 players.

Several of these moves were relatively short-lived.

Emerson Royal eventually joined Flamengo for €9 million after arriving for €16 million. Morata moved to Como on a permanent deal worth €12 million in 2026, while Álex Jiménez was sold to Bournemouth for €18.5 million.

Other signings left on loan or returned to their parent clubs when temporary deals expired.

Santiago Giménez, Milan's most expensive acquisition of the season, joined Porto on loan in August 2026, with a purchase option that can become obligatory under certain conditions.

Fofana also departed temporarily, joining Sevilla on loan in September 2026.

Of the 11 players tracked from this window, Pavlović is the only one currently listed in Milan's first-team squad.

2025/26: A further €157 million

The third campaign featured another major recruitment drive, with Milan bringing in several high-profile names and investing in younger players.

Total investment: €157.00m across 10 tracked players.

Once again, Milan combined substantial spending with short-term experience.

Nkunku arrived from Chelsea in one of the biggest deals of the summer, but returned to RB Leipzig on loan in August 2026, with an option for a permanent transfer.

Ricci joined Como on loan in the same window, despite having arrived from Torino only a year earlier.

Meanwhile, Jashari, De Winter, Estupiñán, Rabiot and Modrić remain on Milan's current first-team roster.

The 2025 window is still relatively recent, making it too early to deliver a final verdict on the long-term success of its signings.

What happened to the money?

Milan have already recovered more than €120 million through confirmed permanent sales of players from these three transfer windows.

The largest completed sales include:

These eight transactions generated approximately €28.77 million more in transfer fees than their original acquisition costs.

However, that does not mean the entire transfer strategy was profitable. Across all 32 players, the original investment was substantially higher, and many departures have generated little or no permanent-transfer income.

The €305.58 million difference is a transfer cash-flow comparison, rather than an accounting loss. It does not include wages, bonuses, amortisation, loan income or the remaining value of players still under contract.

How many are still at Milan?

As of October 2026, 12 of the 32 players are listed in AC Milan's 2026/27 first-team squad.

From 2023/24:

• Christian Pulisic

• Ruben Loftus-Cheek

• Yunus Musah

• Samuel Chukwueze

• Filippo Terracciano

From 2024/25:

• Strahinja Pavlović

From 2025/26:

• Ardon Jashari

• Koni De Winter

• Pervis Estupiñán

• Adrien Rabiot

• Luka Modrić

• Pietro Terracciano is not part of this board; he is excluded from the original 32-player selection.

The distinction between being sold, being loaned out and leaving at the end of a temporary contract matters. Not every player currently away from Milan has been permanently transferred.

So, was the rebuild successful?

Three seasons of recruitment produced some very different outcomes.

Reijnders represents the clearest example of a signing that gained substantial resale value. Pulisic established himself as an important player, while several other investments resulted in transfers, loans or early exits.

The most striking number is the amount committed to players who are no longer regular members of Milan's first team.

But financial outcomes tell only part of the story. Transfer success should also be measured through minutes played, performances, goals, assists, consistency and contribution to team results.

That is where this board comes in.

Rather than treating these transfers as closed chapters, we continue tracking all 32 players throughout the 2026/27 season.

Who is performing best today? Which former signing has found a new level elsewhere? And which expensive transfer might still prove its value?

The original transfer windows are over. The players' careers are still moving.

Methodology: Transfer fees are based primarily on Transfermarkt's historical records. Values reflect reported base fees and selected loan charges, without untriggered bonuses. Permanent-sale totals cover identified completed transactions involving players on this board. Squad membership is checked against AC Milan's published 2026/27 first-team roster. Last reviewed: 8 October 2026.