With such regularity of loosing large bets on big sports events, I might even think of placing the opposite bet Drake does. This looks like a pattern already. Look what Drakes bets on and do different.
I was serious when I have asked if someone remember that Drake has ever won big in gambling. It is either he is very unlucky, or media only stress attention his losses, because people love to see when rich and famous people fail.
In my opinion, it could be a mixture of both the media giving more attention to Drake's losses than his victories and also he may be more unlucky than the average super start music producer/musician out there.
I personally do not have anything against Drake or his fans, but seeing someone like him to lose money in this way is kind of like a reminder than within the wall of the casino, we all are equality subjected to the randomness of the luck and the entropy of the game, you know.
Dices, do not care about your social status, neither do the Plinko ball.
Drake losses could actually play in his favor, people are more likely to feel empathy for someone to lose money than someone who wins and brags about it non stop in their faces. If somehow, he manages to act humble enough while facing those losses, he may end up catching the attention of more people who were previously unaware of his music and projects. Just my two satoshis.