I don't recommend Stake to get Drake as one of their endorsers, Drake has a gambling problem he can bet a huge amount of money because he still can make a lot of money as a concert artist and he also admitted that he has a gambling problem, it's against what Stake.com preaches in their TOS about responsible gaming.
Maybe we can suggest that to Stake but if Stake still wants to hire Drake as one of their endorsers and they've already spent a lot of money, Drake will stick with them. Apart from that, maybe Stake has other considerations for Drake and hopefully, Stake can help Drake cure Drake's gambling problem. And if Drake can overcome his gambling problems, it will lift Stake's popularity because he has helped one of his endorsers overcome his problem in gambling.