The Rossoneri legend has slammed the running of the club in recent times and claims their poor form leaves him feeling both angry and disappointed
The Rossoneri sit 11th in Serie A following a shock 4-2 loss to home to Parma on Sunday, some 12 points off a Europa League spot with 10 game left to play, and were beaten 5-1 over two legs by Atletico Madrid in the Champions League last 16.
And Maldini, who spent 24 years at San Siro, winning six Scudetti and five European Cups, has slammed the running of the club following a second-successive season of disappointment.
"Inside of me there's a mixture of anger and disappointment," he told La Gazzetta dello Sport.
"Not so much because of the results, but because I get the impression they're throwing away what was built with hard work over the last 10 years.
"That makes me feel awful. I know how much work there was behind all those glories, what it took to build such a beatufiul story. It makes me crazy to see everything destroyed.
"They cannot compete with Juventus or the top 10 teams in Europe. There isn't a project."
The 45-year-old has confirmed that he did hold talks with Barbara Berlusconi over a potential return to the club, taking away the sporting responsibilities of Adriano Galliani, whose methods he feels are outdated.
"I had two interviews with Barbara. After the division of responsibilities, I have been touted as the successor to Galliani's sporting duties, but I have not heard from anyone.
"I was ready for a role in sports. Milan have many employees but are missing someone from a sporting perspective.
"Galliani is a great leader, but can't understand players. He does everything himself and this is not possible. If you only sign the players of one Fifa agent, sometimes you can make the deal, sometimes you can't.
"At the bottom of it, there must be knowledge. [Former director Ariedo] Braida played a marginal role in recent years, before there was Leonardo, who helped Galliani understand whether a player was suitable to Milan or not.
"I remember when Leo wanted me at all costs to become sports director, Galliani said: 'We don't need him'."
Maldini also believes that coach Clarence Seedorf has been left with an impossible task in turning around the Rossoneri's fortunes.
"It's obvious that he's not an expert, but he has a lot of courage and personality, but not even Pep Guardiola could do anything," he added.
"This isn't Clarence's fault. [Pippo] Inzaghi spent two years with the youth team and this is important."