Maldini won five Champion's League titles and the Serie A seven times during his 25 seasons with Milan, but he said the side - who currently lie seventh in the league - have failed to show sufficient ambition in recent years.
“I was fortunate enough to be with Milan for 25 splendid years. When I arrived, I found a great foundation to build a great club," Maldini said in an interview with La Repubblica. "President Silvio Berlusconi came and taught us to think big, also of course with his investments.
"Arrigo Sacchi followed and we had the mentality that we’d become the symbol of a style of football. It was something magical.
“Slowly, the magic was lost and Milan transformed into an absolutely normal club. That’s because Milan stopped transmitting that message and those who had written the history of the club stopped teaching their knowledge to the next generation.
"There is nobody in the current Milan set-up who wrote history, other than those in marginal roles."
The former defender also hit out at any notion of a long-term plan at Milan, citing recent transfers as proof of disorganisation within the team.
“It is difficult to evaluate the planning of this Milan side, as over the summer they released 12 players of great character and still didn’t expect a difficult start to the season," he said.
"In all honesty, I can’t see what their plans are. Choosing certain players, even if they are on free transfers, looks a world away from a specific plan."
But despite the criticism, the 44-year-old was quick to deny any ambitions of having his own input or becoming a coach at the San Siro.
“I have never considered being a coach, because I saw the nomadic lifestyle my father Cesare had to go through in order to work.
“I don’t want to be a director because I don’t like politics. If I were to remain working in football, it would be in bringing my football knowledge. There are few who are 100 per cent competent, know about tactics, players and sports psychology. I am not interested in a role just for the prestige of it.”And Il Capitano went on to suggest that several roles had been offered to him, adding: “I’ll reveal to you that Leonardo wanted me at Milanello, even if I was just to stand there and show my presence.
"I told him there was no point in my turning up without a role. Galliani told me and Leo that a director of sport was no longer necessary in football, but I think there is a real need for one.
“Last year, Max Allegri called me and said he needed someone to keep an eye on him, to say whether he’d done something wrong tactically or in dealing with the locker room. He needed someone with the character to talk to the more important players in an authoritative manner. He thought that I, with my past, could do that."Despite the ex-player's reluctance to take on a coaching or advisory role within the club, he did express a desire to see the side regain its former prestige.
“I just want to give the magic back to Milan. I won more than anyone with this club and played more games than anyone, but I feel Milan have given me even more. I feel a debt of gratitude to Milan.”The former Italy captain, who retired from football in 2009, also said former players should have a role to play at Milan, adding: “Look at Bayern Munich and Real Madrid, who had directors like Beckenbauer, Hoeness, Rummenigge, Butragueno, Gallego and Valdano.
"This magic can be carried on and taught by those who experienced and even created it. Milan had the magic for 25 years, but then lost it."