Seven spirits worse than the first
The reference to this wicked generation locates the saying historically. I would suggest that Jesus is talking about the generation of Jews that would suffer the horrors of the war against Rome. He casts out demons from Israel, but he warns that these homeless spirits will return with a vengeance and wreak havoc. The derangement of the possessed who confronted him was nothing compared to the self-destructive madness of those who, a generation later, rebelled against Rome. Josephus describes the lead up to war in these terms…
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