The Portuguese superstar's signing paved the way for a remarkable piece of business that is being lauded by Milan fans but lamented by Juve supporters
Leonardo is no stranger to outrageous proposals. He certainly took Anna Billo completely by surprise when he asked the Sky Sport Italia presenter to marry him live on TV in March 2013.
A stunned and embarrassed Billo didn't say yes there and then; she required some convincing.
However, Leonardo had been confident that his proposal would be accepted and the pair wed just six months later.
The Brazilian's impressive powers of persuasion have generated headlines again this summer.