I knew guys like that in college. Gambled all the time, threw cash around all the time. One week they were rolling in dough, the next they were broke. That's how a large portion of the professional poker players are, too. Easy come, easy go. Scotty Nguyen won the WSOP main event and was broke a week later. He gambled it away playing craps. Mike Matusow has famously been broke a few times in the past 3-4 years.
Maybe he's different, but I doubt it.
Jordan was betting $10k per hole a while back on golf. And while that would indicate a problem on my budget I haven't heard of his airness having any problems with cashflow. We don't know the guys situation so we can't say he has a problem or not.