We tend today to see the gospel as pertaining to individuals and salvation, which in part it is. Jesus is shown here as also seeing the gospel in terms of groups and cities and generations. Just as a man can be inhabited/possessed/re-inhabited so can collective movements and generations. Individuals think and act and behave within groups. Unclean spirits think and act and behave in similar conjunction. In Jesus' time He saw a perfect storm of the two mounting against Him. Though He could be convincing to some individuals one on one at this time, it would not be until His death and resurrection that the true forces driving individuals within masses could be dealt with.
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