Few expected the exit door at Real Madrid to open for the Portuguese superstar, given all that he achieved during a record-breaking spell in the Spanish capital.
There were, however, murmurings of discontent at regular intervals and Milan were among the ambitious outfits to hold transfer talks as a move was mooted in the summer of 2017.
No deal was done at that stage and 12 months later those at San Siro were forced to watch on as a stunning agreement to bring Ronaldo to Italy was reached by old adversaries in Turin.
Fassone believes he took the right decision when snubbing an approach, but has left Milan fans wondering what could have been had former owner Li Yonghong been nudged in a different direction.
“It’s true, Li Yonghong wanted Cristiano Ronaldo at Milan,” Fassone told Il Sole 24 Ore.
“Mr Li wanted Ronaldo at the Rossoneri because he believed he had great strength in the Chinese market.
“The player wanted to leave Madrid. We met in July 2017 with his agent [Jorge] Mendes to check the costs and his availability.
“It was then that I convinced him to give up the dream: Ronaldo was too expensive.”
Money was considered to be more of an issue for Milan than landing a marquee signing when the Ronaldo opportunity presented itself, with financial struggles having hit the club hard in the wake of Li Yonghong’s ill-fated reign.
Fassone added: “I think Milan were led by an excellent board of directors. We made €20m more turnover.
“That €126m debt included €45m extraordinary costs, covered entirely by Elliott and were due to write-downs of players like [Nikola] Kalinic and provisions for myself and the five other directors who left the club.
“I don’t hear from Li anymore, although sometimes I do from his right-hand man [David] Han Li.
“I don’t know where the money came from, but prestigious advisors were involved in the deal so why should I have doubted him?”