Sport Mediaset suggest that the Rossoneri will relieve Clarence Seedorf of his coaching duties at the end of the season, regardless of where they finish in the table.
And with the Dutchman out of the picture, Barbara Berlsuconi will go to the Fiorentina boss and try to tempt him to San Siro.
The former Roma striker may prove difficult to get however, having signed a contract to keep him in Tuscany until 2017.
It is also unclear whether Montella would want to swap Champions League-chasing Fiorentina for middle of the table Milan.
Mediaset though, insist that the Diavolo are looking at the Viola tactician as a potential successor to Seedorf.
And should they get their man, Luciano Spalletti is expected to come in at Artemio Franchi, having been sacked by Zenit St Petersburg in March.
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