I have been following drake for a longtime and I noticed that his gambling win is more announced than is gambling lose, and people will misunderstand everything and think he is a gambler that always wins. People needs to be very careful and not to see people drake as their role model in gambling because his wins are always announced. We don't know the other stories of drake what he may have gone through in his gambling activities, we shouldn't be carried away by his big win.
I believe differently. I mean, almost all his big bets are always announced on social media even before the result of the bet is known; they can be followed up by everyone, and not just the bets that he loses, so it's not always his winnings that are announced. I even think that he has had more losses compared to the winnings we see because of how he has been dragged online for having a bad gambling habit and even accused of making those bets based on promotion.
You can see his history of bets here, win and loses,
https://www.covers.com/industry/drake-sports-betting-history-curse-fact-or-fictionFrom UFC to Boxing to NFL, notably is his bet on Mike Tyson to beat Jake Paul but we all know that it seems like a setup and Jake Paul win that boxing match easily. So it's not that he always win or loses his bet, it could be just like the rest of us, he could be in the negative even if he won like $40 million. But he has a lot of money to gamble, so I guess his bank account wouldn't take a big hit and he can still continue to gamble even if there is speculation that it's like fake money coming from Stake.