How do you know he lost it? Ever hear of ‘money laundering’? I would like to see who claimed and paid the taxes on THEIR winnings. I suspect he just may the money disappear.
Are chapter 11 proceedings in the public record?
Hypothetical: you make a large sum of money disappear and keep it hidden. Then, you file for bankruptcy and get the creditors to settle for less than you owe, and less than you hid. Then, you repay the reduced amount slowly, drawing on the hidden money as needed. In the end, you come out ahead.
Again, this is hypothetical. But, if a bankruptcy settlement is public record,, it mght offer some useful information.
Whatever happened, honest people don’t sell their biggest asset (in this case, a business), then turn around the next day and lose it all gambling.
To me, this is the biggest red flag on his credibility.