Forbes Magazine once did a story on the 10 poorest people in America. It took a lot of energy and IQ points to make that list. Most had been wealthy at one time. I lived near one list member, an elderly mafia lawyer who had lost a judgment to a union he had borrowed from.
Forbes put his net worth at negative $47 million. He lived in a mansion on 4 acres and drove a black Cadillac. I think he reached a compromise where the union let him and his wife live out their remaining few years in their home in exchange for cooperation in marshaling their far flung assets.
When the couple died, the car was a jalopy and their home was terribly run down.