Speaking to journalist Carlo Pellegatti, the three-time Ballon d'Or winner drew a direct parallel between AC Milan's predicament and that of Ajax, the Dutch club he also follows closely.
"Here in Holland I support Ajax a little bit — it's not going great. But it's the same for Milan. Milan is not what it used to be, and I hope they will be able to change the situation, because right now in Milan it's Inter Milan who are in charge — and I don't like it."
Van Basten spent seven years at Milan between 1987 and 1995, winning four Serie A titles and two European Cups before ankle injuries cut short his career at 30. He scored 125 goals in 201 appearances for the club.
He also addressed Italy's failure to qualify for the World Cup for the third time in succession, describing the absence of recognisable international-calibre players as the root of the problem.
"It's a shame. I think Italian football has always been up there, and I hope it returns to Italian hands. I hope Italian football takes back its situation in Europe and starts to lead again — maybe a little more than Spain or England. I saw the national team and what's missing are stars.
"Italy always had a great centre-forward, a great defender, a great goalkeeper, a great midfielder. Today it's difficult to see them. Italy has always been a great football country with great history and great players. Looking at the national team today, it feels a little strange."
On Holland's World Cup prospects, he was candid about his expectations.
"I'll support Holland, but I'm not expecting much. I'll also support Brazil a little bit — for Carlo Ancelotti."
Milan are currently sixth in Serie A with three rounds remaining, on the verge of missing European football entirely. A qualification for Conference League football will likely represent the minimum acceptable outcome for a club of their stature.