AC Milan vice-president Adriano Galliani has announced that he will resign in the next few days.
The 69-year-old has been Silvio Berlusconi's right-hand man at the club since 1986.
His transfer acumen helped numerous successful periods for the Rossoneri over the past quarter of a century.
But he has come under mounting scrutiny and criticism for Milan's transfer policy over the past few seasons when the club has been trying to cut costs.
The seven-time Champions League winners are languishing in 13th place this season after scraping into the Champions League places last season.
Berlusconi's daughter Barbara, who has been taking a more hands on role at the club, is said to be one of the main instigators of Galliani's departure.
Galliani hinted at discord as he announced his resignation:
"I've suffered grave damage to my person. This is not the way to deal with a generation change. It should be done with elegance. I will be resigning with just cause in the coming days, or maybe I will wait until after the Champions League game with Ajax."