Jesus said to the chief priests and elders of the people:
“What is your opinion?
A man had two sons.
He came to the first and said,
‘Son, go out and work in the vineyard today.’
He said in reply, ‘I will not, ‘
but afterwards changed his mind and went.
The man came to the other son and gave the same order.
He said in reply, ‘Yes, sir, ‘but did not go.
Which of the two did his father’s will?”
They answered, “The first.”
Jesus said to them, “Amen, I say to you,
tax collectors and prostitutes
are entering the kingdom of God before you.
When John came to you in the way of righteousness,
you did not believe him;
but tax collectors and prostitutes did.
Yet even when you saw that,
you did not later change your minds and believe him.
Matthew 21: 28-32
We sometimes do not appreciate the power of a Bible text due to a lack of historical knowledge. That is the case where Jesus notes that repentant tax collectors and prostitutes were entering the Kingdom before the chief priests and elders. The shocking nature of this statement would have been immense to those who heard Jesus. For the Jews of the time of Jesus family and ritual purity were everything. A harlot was severed from her family and her paid fornications made her unclean and everyone who had the slightest contact with her unclean. The destruction of the Temple by the Romans was blamed in the Talmud upon widespread prostitution and the same prostitution was regarded as a sign that the Messiah would soon come. That the Messiah would allow prostitutes into His presence would have seemed to many pious Jews as a sick parody of their beliefs.
As for tax collectors, well, I doubt if “revenuers” have ever been popular people in any society. However, tax collectors were especially hated by the Jews as collaborators with the Romans and parasites who ground the substance of their fellow Jews for the benefit of their occupiers. The Romans sold the rights to collect taxes throughout their empire to syndicates. These syndicates, often with powerful Senators as silent partners, would then have the right to collect taxes from the subject populations in a region. The more they could wrench from people usually living at a subsistence level, the higher their profit margin. Thus tax collectors like Matthew earned an enmity far greater than our term tax collector can convey.
Jesus highlighted the unlikely converts He was making in order to demonstrate the power of the grace He was bringing and the terrible misunderstanding of the Jewish religious establishment of what God demanded for salvation. The Gospels seem so familiar to us that we fail to understand how shocking they often are, a shock that was fully intended by Christ.