Having spent sometime with people who are actually addicted to gambling it makes it obvious that neither of these celebrities are addicts, they are just famous and it will make an attractive story to make them up to be one.
- Jay -
He gamble because he has promotion deal with that big casino so expect that we see him gamble from time to time since its provably part of promotion. If he doesn't have anything like that for sure we can see him gamble in minimal manner since for sure even if they are rich they are aware about any unnecessary loss from gamble since there are professionals handling their finances. Same with Michael Jordan for sure he is not in situation where he can't control his gambling activity since if he's really into abusive situation especially on gambling scene for sure this is a large scope for media and this will be in news. But we don't actually see that so I guess same with Drake they are just spending some time having fun gambling and they didn't take it seriously since they have other more business that need to deal with that's why Jordan became billionaire since he is busy on his businesses and other basketball related activities.