Former Italian prime minister Silvio Berlusconi agreed on Friday to sell the club to a consortium of Chinese investors, ending his three decades of ownership.
Although much of Berlusconi's reign was hugely successful, his last few years were a tale of midtable mediocrity, unsuccessful transfers and musical chairs in the coach's hot seat.
Milan won Serie A eight times and the Champions League on five occasions under Berlusconi but the titles dried up after their last league title in 2011 and the last three seasons have seen them stagger home in eighth, tenth and seventh place.
The club appear to have been unable to adapt as Serie A, once Europe's most prestigious league, has fallen behind its English, Spanish and German counterparts.
At first, the club's leadership pledged to put their faith in young players, only to go out and sign players in the middle or latter stages of their careers.
One example was their decision to bring Brazilian midfielder Kaka back for a second stint at the club in 2011 in a classic case of what Italians call "reheated soup."
Other failed signings of players attempting to revive flagging careers included misfiring Spain forward Fernando Torres, Ghana midfielder Michael Essien and maverick striker Mario Balotelli.
Coaches came and went with bewildering frequency and, since January 2014, Massimiliano Allegri, Clarence Seedorf, Filippo Inzaghi and Sinisa Mihajlovic have all been fired.
Cristian Brocchi, in charge for the last few games of last season, walked out last month and was replaced by former Sampdoria and Fiorentina coach Vincenzo Montella.
"It is fundamental for me to feel supported, so people have confidence in me," said Brocchi.
"We did not have the right conditions to continue, so my decision to walk away was right for the good of the club and the good of Berlusconi."
The job of rebuilding will now fall to Chinese investors including development and investment fund Haixa Capital and Yonghong Li, chairman of management company Sino-Europe Sports Investment Management Changxing.
Berlusconi's Fininvest family holding said it had signed a preliminary agreement valuing the club at 740 million euros (£627.4 million) including 220 million euros of debt.
Neighbours Inter Milan have been under foreign ownership since a consortium led by Indonesian business tycoon Erick Thohir bought a 70 percent stake in the club in November 2013.
But Inter have failed to qualify for the Champions League since then and changed hands again in June when Chinese electronics retailer Suning Commerce Group Co Ltd bought nearly 70 percent of the club for 270 million euros.
Suning’s first few weeks have been marked by rumours that coach Roberto Mancini is unhappy with them and is threatening to quit with a year of his contract to run.
Both Milan teams, who share the run-down municipally-owned San Siro, find themselves lagging behind Juventus, who have won Serie A for the last five seasons and are looking more dominant than ever.
Unlike the two Milan sides, Juventus are proud owners of their own stadium, giving them a precious, extra source of revenue.
And, with Juventus raking in prize and television money from their regular appearances in the Champions League, the gap between the Turin side and their Milan rivals only looks as if it can get bigger.
(Reporting by Brian Homewood; Editing by Rex Gowar)
