It is believed that the Rossoneri are close to signing the one-time capped Italian worldwide as part of a sensational swap deal that would see veteran centre-half Leonardo Bonucci return to Juventus only a year later after he had left Turin for Milan. Caldara is showing a huge amount of potential for a young player and would be a solid replacement should Bonucci leave. The 24-year-old defender has signed a contract that binds him to AC Milan until 30 June 2023. They have secured goalkeeper Mattia Perin from Genoa to fill in the void left by Gianluigi Buffon.
So here are 12 of the other players to have worn both iconic shirts.
Dharmesh Sheth has revealed that Gonzalo Higuain is edging ever closer towards a transfer to AC Milan ahead of Chelsea FC this summer. He has many players who can play with four in the back, three in the back, five in the back, so he is the one to decide.
Manchester United, Barcelona and Real Madrid have all been credited with interest in Willian.
Critics, however, say he has failed to make an impact on the big occasion.
What are 3-D printed guns?
The "ghost guns" blueprints have already been downloaded thousands of times since they were leaked online this week. After a years-long court battle, the state department in late June settled the case against Defense Distributed.
Milan appeared to have beaten Chelsea in the race for the Argentina global after earlier reports claimed a deal worth in the region of £49m had been agreed with Juventus.
As seen at Napoli, he thrives with two wingers on either side of him.
His arrival at Allianz Stadium comes as Higuain finalises an expected loan move to Milan with a view to signing permanently at the end of the season. They've acquired a defender who has proven he can deliver in the short-term and has an even brighter future, and a world-class striker that has been desperately needed for years. The club has worked very well and after this week of work we will go back.