Leonardo has resigned from AC Milan after just a single season as sporting director, the Serie A club confirmed on Tuesday.
The Brazilian joins Gennaro Gattuso in choosing to stand down after Milan narrowly missed out on securing Champions League qualification.
It marks the fourth time Leonardo has left the Rossoneri, having spent two separate stints at San Siro as a player and one as head coach.
He returned as sporting director in July 2018 and was responsible for overseeing the club's transfer market activity.
"Leonardo joined AC Milan in its hour of need a few short weeks before the closing of the summer transfer window," Milan CEO Ivan Gazidis said.
"Under very difficult circumstances he put his heart and soul into addressing a highly complicated situation and transmitting his energy and his ambition to the team.
"I am very grateful to Leonardo for everything he has contributed to our great club and wish him well in his future endeavours."
Leonardo has been linked with a move back to Ligue 1 champions Paris Saint-Germain, where he previously worked.Published 28 May 2019, 21:18 IST