AC Milan’s summer planning is already taking shape behind the scenes, and according to CM, a significant portion of their potential transfer income is all but secured. Of the €94 million in possible buy-out clauses tied to players currently out on loan, around €65 million is considered almost guaranteed. That figure alone would represent a major boost to Milan’s financial flexibility heading into the next window.

The Rossoneri have strategically structured several loan deals over the past two seasons, inserting options or obligations to buy depending on appearances, team objectives, or survival clauses. Now, those calculated risks are beginning to look like smart business.

At the forefront are players whose buy-outs are either automatic or highly likely to be triggered. In some cases, the conditions are straightforward — a set number of appearances or the purchasing club avoiding relegation. Where those benchmarks have already been met or are close to being achieved, Milan can effectively start counting the income.

For example, one loanee’s deal may include an obligation to buy worth around €15 million if his club secures top-flight status. With only a handful of games remaining and a healthy league position, that transfer is edging closer to certainty. Multiply that scenario across several players and the projected €65 million begins to make sense.

This guaranteed portion of revenue is crucial. Milan are operating in an era of tighter financial controls, with squad sustainability and wage balance just as important as performance on the pitch. Securing roughly two-thirds of the potential €94 million means the club can plan with greater clarity. It allows the technical directors to identify reinforcements early, negotiate from a position of strength, and avoid last-minute panic buys.

However, the remaining €29 million is less secure. These are cases where options to buy exist but are not compulsory. The purchasing clubs may be weighing up performance levels, financial constraints, or alternative targets. In some instances, players have impressed but not consistently enough to make the decision automatic.

That uncertainty introduces an element of risk. If even half of that €29 million fails to materialise, Milan could see a notable gap between projected and actual income. Yet there is also a potential upside. Strong finishes to the season, managerial backing, or market demand from third clubs could still swing decisions in Milan’s favour.

Beyond the numbers, there is a sporting dimension. Offloading players permanently reduces wage commitments and clears space within the squad list. Milan have been focused on lowering the average age of their core group while retaining resale value. Permanent exits for fringe players align with that strategy.

It is also worth noting that structured exits signal stability. Rather than scrambling to sell assets late in the window, Milan have anticipated departures well in advance. The result is a smoother transition cycle — outgoings feed directly into incoming recruitment.

Ultimately, the headline figure of €65 million almost guaranteed out of €94 million represents more than just accounting optimism. It reflects careful negotiation, calculated risk, and a forward-thinking approach to squad management. If the remaining clauses fall into place, Milan could approach the summer with nearly €100 million generated from outgoing loanees alone — a powerful platform for the next phase of their rebuild.