It’s like a conservation agreement. The land (wealth) remains in control of the owner, but the state gets some say in its use and the public benefits. Abuse of the the system is a case for stricter enforcement; sanctioned but objectionable uses are a case for stricter regulations
It's almost never investigated, and there is, in the normal course, so much overlap between expenses that benefit ME as a person, and ME as the owner of the charity.
Travel is a big one, for example.
More pedestrian stuff (eg expensing a conference in Seychelles) definitely slips through, but we could make the same principal-agent complaint about business expenses or other settings where one person gets to spend money from different buckets that are taxed differently.
I’d challenge the notion that the rules are unenforced though - someone will have questions if you’re living in a house your foundation purchased or somesuch. At the very least several people with an obligation to know better and much less to lose we’re going to be very nervous.
Conversely, even a charitable organization not run by the donor may be heavily influenced by a disproportionate donor such that it is de facto controlled by them.
Our former president would beg to differ
[0]:https://ag.ny.gov/press-release/2019/donald-j-trump-pays-cou...