Why did Jesus say that the last state of the evil generation of his time would be worse than the first?
This parable about the evil spirit’s return (Matthew 12:44–45) is a warning for all who reject Jesus: that the generation of Jews in his day—even while casting out demons (Matthew 12:27) and seeking to resist Satan—still rejects the power of the kingdom of God present in Jesus: the Holy Spirit (Matthew 12:28)—making the nation more and more an instrument of Satan. The Jewish people experienced Satan’s ongoing activities, since it had given itself over to him, but Christ came to free them (as seen in his repeated victories over Satan: Matthew 12:25–30).
The delivered person in the parable thinks that after being freed from one demon, he is safe, but many others come with more destructive and corrupting power, making the final condition of that man worse than the first (Matthew 12:45), so it is better not to be freed at all than to be freed without turning to the true Liberator. So it will be with this unbelieving generation of Israelites
By means of this parable about the unclean spirit returning to its former house (Matthew 12:44–45) Jesus highlights that the generation of Jews in his day—though preoccupied with casting out demons (Matthew 12:27) and attempting in their own way to resist the evil one—still refuses to accept the true power of the kingdom of God present in himself, namely the Holy Spirit (Matthew 12:28). As a result, they fall into an even more grievous condition.1
There was also among the Jewish people constantly ongoing activities of Satan, which could of course not be any other way given that the nation had given itself over to him. Christ came to set them free (and one may assume that his repeated victories over Satan recorded in Matthew 12:25–30 correspond to the demon’s temporary withdrawal following his defeat). Yet because they refused to listen, their inevitable fate was that the nation as a whole would become more and more of an instrument wielded by Satan for his evil ends.2
The kingdom of demons is mightier and more varied than the delivered person realizes in his naïveté. He imagines that after being freed from one demon he is safe. But there are many others with greater destructive and corrupting power. The expelled demon brings seven others worse than himself, and they settle in the empty house as a destructive collective. As such, Jesus highlights, the final condition of that man is worse than the first (Matthew 12:45). It is therefore better not to be freed at all than to be freed without turning to the true Liberator. So it will be with this unbelieving generation of Israelites. Jesus’ parable is meant as a warning for all who reject him.3
45 Then it goes and brings with it seven other spirits more evil than itself, and they enter and dwell there, and the last state of that person is worse than the first. So also will it be with this evil generation.”