Having a debate with an Italian guy about who is the bigger club and I think it’s close.
Both have won their domestic league 19 times and Milan have 1 more Champions League.
Milan probably have more well known legends like Van Basten, Kaka, Maldini, Gullit and Pirlo. But in recent years Liverpool have had Gerrard, Suarez, Alonso, VVD and Salah.
The current popularity of the Premier League helps Liverpool but Milan also has a huge fanbase.
I also don’t think prosperity is the right word, but the point remains that Milan is the bigger city of the two
Liverpool has around 500K population, while Milan is almost triple that, and around a 3.5M metropolitan area around it, and with several global brands headquartered there etc etc