I can loan him in one condition he needs to be sober and stop gambling for at least a month to show that he is not using the money for gambling and it will be under close monitoring and supervision.
Its hard to grant a loan to anyone who is deep into gambling even if you are close to him or you owe him something, lending him will just give him money and reason to continue gambling in the hope that they can get all their losses back.
There is no point in us monitoring them, because when someone is addicted to gambling, they will usually use various ways to avoid us, because all they have in mind at that time is how to make the game run smoothly. Indeed, on the one hand, it is a difficult choice for us if there are people who actively gamble asking for loans, especially if we have debts to them so that we are forced to give them loans so that we are not considered as people who do not know how to repay their services, but we are only allowed to lend it once and after that we are not allowed to lend it again so as not to cause internal problems with them.