Man United owners did a notoriously poor job at managing the team when they bought it.

They're also American which means they're not there to do some ridiculous patronage, neither they're like the 90s local businessmen owned clubs that overspent for patronage - the club has to be useful: it's either need to be profitable, or help enough in making business deals and approach the local business environment.

Milan current owners are also American, and unlike United, they did a good job with managing the club. The club is getting more successful with them. They got the club ownership as payment for debts from the previous owners (spending less than the price coming from actually purchasing it) and besides a very small profit, their intention is that of building a new stadium - and with that, have the privilege to purchase the estate around beforehand for cheap and build luxury apartments for a fat profit.

The current situation in the Premier league is very strange, the club expenses of the big teams are far more than they could get with revenue, they're surviving because they're owned by natural resources barons like Romanov before the war or the United Emirates in City.

Liverpool is the odd man in the Premier league, they're off the norm in all manners (they're lucrative, they don't have any ridiculous debt with billionaire owners, they're among the six most successful clubs in premier league, they've been second most successful club in Premier league last few years, they succeed by making careful spending and thinking through any player purchase to see if it fits the team's strategy and if it doesn't wreck finances)

United is the other direction, worst performing club of the big 6, the one in the worst financial situation, they purchase randomly and change administration often.