Very possible.

There could be reasons why a gambler that has quit for life can be back on it. But I think that the second time around won't be as severe as before.

Because if they've experienced gambling addiction and it has lost them a lot of their possessions, they will do it with extra care.

I also believe that if they're not careful, they'd be more severe just as what the parable has given as an example. But we're not all the same while we can have it as an assurance that an experienced person will definitely be more careful.