Where will this magical LW come from? Maldini paid 30m for Leao and it took him 3 years to reach this level. For Milan to organically replace Leao it will be a similar style of transfer and Milan will lose their catalyst. At the very least this will result in Milan taking a massive step back when it's on the cusp of the European elite
I don't fault Maldini for Dollar and Kebab but Kessie was 100% a blunder, anyone justifying it is delusional
I know Maldini's time horizon for Milan to become a European force is still another 2-3 years, but Leao might force some cards to fall way faster. This season is a critical junction - one because it is the first of the RedBird era, but also because of Leao's future, and how that could impact the project either way. I think we'll need to pay Leao Ibra-money - if we don't, someone else will. If we pay Leao Ibra-money, it will set the standard for the rest of the team and the market that watches. Leao will be the big driver of wage increases, and this will happen this season, not in 2+ years when Milan is flush with cash.
If this happens, Gazidis role will be crucial, and how Maldini plays this may be more important than his team-building prowess. We all know the new stadium will be the big revenue injection that elevates Milan back to a financial powerhouse, but that could be 5+ years away. In some ways, the onfield performance is accelerating too fast from this perspective, because the more successful Milan is, the more valuable its players become, the more expensive to retain they also become. It is critical that Gazidis can leverage this success into realised commercial value at a faster rate than the cost of maintaining this success. So far, he is doing well in this regard.
Speaking of costs, which
@papaberlu eluded to, are the sunk cost and opportunity cost that Milan will suffer if Leao walks. The sunk cost of 30m plus 3 years of development and the continuity lost. The opportunity cost of both Leao's continued ascendance and the replacement's time to gel and develop into an effective replacement. It will be interesting to know at what weight Milan measures these. The sunk costs are immediately realised if Leao leaves, which sucks. But it's the opportunity cost that is super interesting - I'm of the reluctant opinion that if Leao were to leave, Milan would be okay. Milan would have a plan to reduce this cost as much as possible. They have precedence on this - Dollar for Maignan the best example, as this was a net positive.