Drake has a lot of money to bet using any money he has. I wonder if he regrets placing such big money and will not place another bet. But I guess he will not stop because he will want to recover from his loss. It is normal if he thinks like that.
He has a history of placing bets and losing a lot, whether he wins or not he will still bet and will continue to bet as long as he can afford to bet and lose, Drake is still popular and can still rake millions but he'll regret this for the rest of his life, I think he's now a compulsive gambler based on the articles I've read about him on gambling, this is one personality who doesn't care about money.
Some people like to spend their money by gambling, I do not see a problem with that if they are rich enough. This dude probably earned hundreds of millions of dollars all his life, spending just 1% of that is not really that weird if you ask me. Plus, he probably gets some sponsorship from the places he gambles as well, so even if he doesn't get monetary help, he probably gets some bigger cash back and all for sharing it, so if he loses, he will probably get like 10%+ of it back.
I would guess that picking crypto was a bit more tax related reasons as well, if he earns that back, he would have to cash that out to pay taxes, so he could just keep that in and keep on gambling.