A five-time champion of Europe with Milan, Maldini also lifted the Serie A title on seven occasions during an illustrious playing career at San Siro spanning 25 seasons.
Milan have failed to achieve success this term, however, and currently lie 11th in Serie A, 40 points behind leaders Juventus and 23 adrift of the final UEFA Champions League qualifying berth.
Clarence Seedorf - a former team-mate of Maldini - replaced Massimiliano Allegri as head coach in January, but his arrival has failed to spark a revival and Milan have lost three straight league matches, with Sunday's 4-2 defeat to Parma marred by protests from supporters.
Milan also exited the Champions League courtesy of a 5-1 aggregate reverse against La Liga high-fliers Atletico Madrid earlier this month.
Maldini says it is not necessarily results that concern him, but rather the way the club's history of success is being "thrown away".
Speaking to Gazzetta dello Sport, he said: "I watched the game (against Parma), as well as the match with Atletico and nearly all of those of the past two years.
"Inside me there is a mixture of anger and disappointment, not so much for the results, because the club has previously been 10th or 11th, but because the impression is that they have thrown away what was built with hard work over the previous 10 years.
"For me this is very bad. Milan have had the good fortune of having many winning cycles with similar synergies of men. I know how much work there was behind so many triumphs, what it took to build such a beautiful story. To see it all destroyed drives me crazy.
"There is no project; they look at today and not tomorrow. You have to buy players functional to the game, do not sign only on a free. You may get it right sometimes, but not always. And then if you hand out a colossal contract, it serves no purpose. But the problem is structural."
Milan's troubles have extended to the boardroom this season, with reports of unrest between Barbara Berlusconi and Adriano Galliani, who share the role of executive vice president and chief executive.
Asked about the duo, Maldini said: "Should Galliani stay or go? It is not for me to say. I think that when you feel all powerful, it is not clear that the results were obtained thanks to others. To win, we want ideas, design, passion. At Milan there remains only passion. It is not enough.
"Can Barbara Berlusconi lead Milan? I do not know. It depends on those around her. I do not think she is an expert on football and footballers."
