Negative Net Worth is not an issue that Trump wants to bring up.
If memory serves, he has - on more than one occasion - gone bankrupt and had to be bailed out by the very banks to which he was beholden.
In fact he might have been the origin of that old saw about being “too big to fail.”
Trump personally went bankrupt?
Some have a grave misunderstanding about what happens when a company files bankruptcy. The laws are different than from personal bankruptcy laws. I think a lot of them do a reorganization. It doesn’t mean they are losing everything they own.