His once-mighty club may be languishing in eighth place, 42 points off first place, but former AC Milan striker Daniele Massaro does not seem too peeved by the current state of affairs.
The Italian, in a sharp black blazer and eagerly obliging photographers at the Marriott Hotel yesterday, wore a genial smile even as he spoke about the Italian football giants' decline.
The Rossoneri were at the height of their powers in the late 1980s and early 1990s, bagging four Italian Serie A titles and three of their seven European triumphs between 1988 and 1995.
This season, however, they trailed far behind champions Juventus in the Serie A, and suffered a humiliating 1-5 aggregate defeat by Atletico Madrid in the round of 16 to crash out of the Champions League.
Yet, Massaro is confident the club can climb out of the rut.
Said the 52-year-old, who is in town for the launch of the AC Milan Soccer School Singapore: "This year, we started badly and we changed coach midway through the season.
"It is also (Clarence) Seedorf's first season as coach. Next season, without the Champions League, we will try to win the Serie A.
"We sold Zlatan Ibrahimovic and Thiago Silva so our bank balance is good. Hopefully, we can be at the top next year."
From a broader perspective, Milan's decline is in tandem with Italian football's fall from its perch in Europe. It is a far cry from 2003, when the Champions League final was an all-Italian affair between Milan and Juventus.
In the past six editions, however, just one Italian club - 2010 champions Inter Milan - reached the final. The same period saw four German teams, two Spanish sides, and five English clubs make the finals.
And Massaro puts it down to the lack of a big-spending owner in Italy.
He said: "We don't have clubs who can spend a lot of money. Only Juventus have this capability. That is the problem.
"Italy used to be the choice of many top players in the world but, because of a lack of money, it is no longer the case."
The recent slide aside, the 1982 World Cup winner is certain the Milan style - one of high-intensity pressing, breaking at speed, and a sense of collectiveness - is still the way forward for both club and budding footballers worldwide.
Said Massaro, who will host a meet-and-greet session with fans at Rainforest Sports Hub at 5pm today: "Since this programme started 12 years ago, we have been trying to pass on (former coach) Arrigo Sacchi's legacy, which teaches unique tactics, technique and a team mentality to the children.
"Yes, at five to six years old, kids always want the ball. But here, we teach them to be selfless, to play for the team and not for themselves.
"Having the right mentality and always working hard, this is most important."
