The guy came from an elite background and has been a lawyer for over 20 years. He has held good paying public sector jobs or worked for one of the largest law firms in the country. It's not like he has been handling indigent cases in the Rio Grande Valley for the last decade.
Even public sector attorneys make good money. Not great money, but decent. Add in his time at a major law firm, where he was paid very well, and I have a hard time figuring out how he ended up so poor.
I don't think I personally know any attorneys with more than 10 years experience who have a net worth of less than $500k. Sure most of that will be home equity, but he doesn't even have much of that. And I know far more attorneys who don't have big firm pedigrees than do. None of my close friends went to Harvard or Yale.
That really does speak to someone desperate to look wealthy instead of accepting the fact that they are not actually that wealthy. That is actually a bit frightening to me.