Ivy ^^probably because the people he had were not good business people who knew what to do, like Branca. They were probably people who claimed they could do great things, but were really more interested in getting something from the relationship with Michael & the deals that were made. There is this idea that because Michel had debt he surrounded himself with yes men, but how about the simple reason that these men were not there to do anything to help Michael's fortune in the first place, but to use his influence, opportunities, talents to amass money for themselves. Not all employees are there for the same ethical purpose.
Another thing about this debt you mention, the very rich have more debt than that, but the way they do not fall into any of these pitfalls, is that they have competent people who are trained in high finance, etc., & it is their responsibility to make sure these debts are acquired, monitored, & paid in a responsible way. They even look at more alternative ways to attract backing. However, Michael had none of these people, so I see it not that the people were yes men but that they were not the best qualified for the positions they hold. Few artists are financial wizards, & unscrupulous men it seems find ways to make Michael think they knew what they were talking about.
Look at Michael list of people around him, Bain, Cascio, Weisner, Thome, Muarry, & the long lists of names--how qualified are these people to do the job they claimed they are aces in? I remember reading the beginning of Aphrodite book where you have Michael's people speculating on how much money they will make. To me, that is the problem with all his staff. They were incompetent.
