Maldini had once rejected an offer from Carlo Ancelotti to become the team manager at Chelsea.
AC Milan legend Paolo Maldini could end his exile from football if the Chinese consortium buying the seven-time European champions gave him a "direct role of responsibility".
With seven league titles, five Champions League trophies and 902 appearances in Serie A where he played 25 years with AC Milan, Maldini is one of the club's most emblematic figures.
However the 48-year-old has remained an elusive figure in the sport, until now.
After years of watching from the sidelines as Milan drop further down the pecking order of the domestic and European game, Maldini hinted he is finally ready to return.
But only if he is offered a role which allows him to have a direct say in what happens on the pitch.
"I've been told that the objective is to hoist Milan back among the top five clubs in the world," Maldini told La Gazzetta dello Sport on Wednesday.
"But that means working 24 hours a day for a very long time. I am prepared to do it, but I have to fully understand the situation at the club.
"I have to meet directly with the future owners and find out their full intentions.
"I still have a deep love for this club and I can only help if I use my heart and my head. If Milan is to benefit, I have to remain true to myself."
Maldini has met "four times" with Marco Fassone, who was appointed to a key administrative role by the future owners, Sino-Europe Sports Investment Management Changxing, last August.
He has also spoken "for 10 minutes on the phone" with Han Li, a vice-president of the consortium which has been negotiating the sale of Milan with owner Silvio Berlusconi's holding company, Fininvest.
"He told me they really wanted me at Milan, but we didn't get any further," added Maldini.
"The job would be hard, and a challenge. I would be leaving the tranquility of my life behind to put myself back in the game, so I need to know everything. From the owners," he added.
After years of crisis, Milan fans would likely welcome Maldini back with open arms.
He is still considered one of the greatest ever defenders and, along with other key Milan players, came to symbolise the Italian giants in their heyday.
However Milan's future owners better come prepared to the negotiating table.
"I'm not in a hurry and, to be honest, I don't think I need to be given the enormity of the project that lies ahead," added Maldini.
Months after his retirement from the game, following a 3-2 San Siro win over Roma in May 2009, Maldini rejected an offer from Carlo Ancelotti to become the team manager at Chelsea.
He also turned down an offer to become Milan's general manager in December 2013.
He added: "I realise I might come across as complicated, but my character and my approach to sport and to life made me into the man I am and who I was on the pitch.
"I have to be like this: we're talking about Milan. It's no laughing matter."