Two points:
On his divorce, I heard he wrote her a check for $900+ Million.
Also heard his ex-wife wouldn't cash the check, because she wanted more.
That, my friends, takes a lot of balls.
On losing his money, when oil prices started falling in late 2014, he came out publicly and stated that he had faith in the industry. Don't remember exact details, but, like most oil companies, he had lots of his production hedged. He stated that he was so confident in the oil market, he was going to cancel 100% of his hedges. When oil prices stopped in the mid $60's last summer, it hurt quite a bit. When they fell below $30 in the winter, he lost billions.
That's probably not the full story on his losses, but it was a big part.