I doubt Chrissy was ever worth $500k, but I do think he chunked off everything gambling a few years ago, then scammed his way back into a bankroll (or got Stacy to cash out her retirement), and then ran it somewhat back up at the end of 2019 and early 2020.
Then he chunked it all off again.
Now we get this video talking about how he lost everything "in the past" and the same thing totally isn't happening right now.
I did enjoy the story around the 8:15 mark where he talks about how Stacy's parents hated him, and told her to divorce him, because he's a "loser" who will "drag her down". They were right!