How complacent could this guy be if he didn't even see his personal assistant spending beyond his means?

NazcaC2
Exactly. And, who would be stupid enough to give someone with a record access to their bank accounts.

Depends on the record.  There are those out there with ivy league educations and a felony for marijuana that are perfectly trustworthy for those matters, and then there are those that have no record and are perfectly qualified for these matters and they will find a way to legally rob you blind.  It is a matter of giving access to a qualified individual while still controlling the situation.  In this scenario, it seems that keeping track of their money was too burdensome. But forget a felony, I have a cousin that was an outstanding lawyer and he was set up by the police when he was drinking alcohol with them and they persuaded him that he would be fine to drive and when he left, one of their on-duty buddies arrested him and now he cannot practice law anywhere in the country.  It is too easy to trust others and become a victim, having certain felony offenses fail to represent that person's morals.  The 2008 movie Felon is a perfect example of this which is based on a true story.