Well, Drake has the means to satisfy his gambling urges. While he may have the money to do so, it still sucks to see a person losing this amount of money due to reasons beyond his control. While he may have betted on the right person, the situation got out of control which made his fighter disqualified in the end.

Even if we may argue that Drake is rich, still, that kind of amount would be a life changer to anyone. Though this may be the case, he is still rich as he is one of the ambassadors of Stake, which is considered one of the most popular gambling website as of this date.

I just hope that this "curse" gets removed or converts to something in a positive manner.