If he becomes their endorser he will gamble more because he is getting more money besides doing a concert and he will enjoy perks that Stake.com is going to offer, to make him play more and how will Stake.com help Drake overcome his gambling, will they offer him to take professional help and fund his healing session, it's like Stake.com helping Drake to dump them,

Remember part of the healing is dumping anything related to gambling and Stake is one of them.
Hopefully, Drake can get over his gambling problem and even though he uses more money from the sponsorship, Drake can also fix his problem. We can only hope for the best for Drake because we don't know what Stake will do to their endorser but I think Stake will help Drake heal his problem. Yes, Drake will get more perks from Stake since he's already promoted Stake. And hopefully, all of that doesn't make Drake have more problems gambling and realize about losing in gambling.