Jesus said to them, “Truly I tell you, the tax collectors and the prostitutes are going into the kingdom of God ahead of you.” (Matthew 21:31)
Of all the confronting things Jesus ever said, this may be the most scandalous. It is not just the content. It’s the audience. Jesus is speaking directly to “the chief priests and the elders of the people” (Matthew 21:23).
These were the spiritual authorities, their ordained leaders, the guardians of Israel’s religious life. These were men of discipline, learning, and piety, yet Jesus says that the tax collectors and the prostitutes — the very people they despised — were entering the Kingdom of God ahead of them!
It is shocking enough that Jesus names these two groups, but it is even more shocking that He lumps them together as, apart from the fact that Jesus accepted both groups, they really had nothing in common.
First century Jewish tax-collectors were wealthy collaborators. They were people who had responded to the Roman occupation by saying “if you can’t beat ‘em, join ‘em”. They worked for the foreign occupying power – taking your money and giving it to the enemy (after taking a healthy cut for themselves). They were traitors and they were understandably reviled. They were sinners by choice.
People who worked in the first century sex industry, on the other hand, were almost certainly not there by choice. Most would have been slaves. They could be violated by their owners at any time or loaned or rented out by their master or mistresses to others for sexual services. These people did not own their own bodies!
Mind you, when I worked with people in the sex industry back in the mid 1980’s, their situation wasn’t a lot better. I was then with the Anglican church in Kings Cross – the red-light capital of Sydney – and I worked with young people on “the wall” on Darlinghurst Road which was where these boys and girls lined up to ply their trade.
I ran a Friday-night coffee shop outreach in the church grounds that targeted ‘the wall’, and all those I engaged with were under 18. I remember one girl telling me how she’d been on the street since she was 12. I’ve never forgotten her story as to why she left home, but I will not repeat it here. Suffice it to say that the sex industry was not a chosen career path for any of them. It was where life had spat them out.
“Tax collectors and the prostitutes are going into the kingdom of God ahead of you”,
These two groups, in a sense, cover the full spectrum of human brokenness – the powerful and the powerless, the exploiter and the exploited, and we see something of their spiritual condition in the parable Jesus gives us immediately before this pronouncement – namely, the parable of the two sons:
“What do you think? A man had two sons; he went to the first and said, ‘Son, go and work in the vineyard today. He answered, ‘I will not,’ but later he changed his mind and went. The father went to the second and said the same, and he answered, ‘I go, sir,’ but he did not go. Which of the two did the will of his father?” (Matthew 21:28-31)
If you’ve had teenage children, this parable probably strikes a familiar chord.
“Can you please clean you room?”, you ask wearily. “Sure thing! No problem! I’ll get right to it” is the enthusiastic reply, so you leave it be for a couple of hours, for a couple of days, for a couple of weeks … nothing.
Jesus contrasts this boy with his brother who, when you ask him to do his chores just stares back at you with attitude, though he does later relent and comply.
Which sort of teenager do you have? Which sort of teenager were you? Which brother did Jesus see in the chief priests, elders, tax-collectors and sex-workers?
In truth, neither of these sons is anything to write home about. The chief priests and elders say the son who does what he’s told is the better of the two but, personally, I prefer to get the response of enthusiastic compliance rather than ‘talk to the hand’.
I think the key here is to recognise that both kids in this story are their father’s sons, and at the end of the story they are still their father’s sons.
The father doesn’t have any perfect sons or daughters. All His children are difficult in their own way. Some are lazy and recalcitrant and some make a better job of it and are first in line when everybody gets to go home but, in the end, everyone does go home. Jesus isn’t saying that there isn’t room for His religious antagonists in the Kingdom of God. They’re just further back in the line behind the people they despise.
“For John came to you in the way of righteousness, and you did not believe him, but the tax collectors and the prostitutes believed him, and even after you saw it, you did not change your minds and believe him.” (Matthew 21:32)
That’s the final puzzling statement from Jesus in this passage – puzzling because I’m not sure what repentance looked like in the case of tax-collectors and prostitutes.
Yes, we do see two examples of tax-collectors repenting in the Gospels. Matthew, the tax-collector, walks away from his job (Matthew 9:9) while Zacchaeus, a more senior tax-collector, shows his repentance by making restitution to anyone he has defrauded and by giving away half his wealth (Luke 19:1–10). In the case of first century sex-workers though, repentance may not have been quite so clear cut.
If you were a sex-worker because you were a slave, no amount of repentance would find you another job, and even if you weren’t a slave, if you were living in a small farming community and were known by your trade, you couldn’t just decide one day to go get a job at the bank. Your options were very limited.
My guess is that many of those whom Jesus saw as leading the march into the Kingdom of God were tax-collectors who were still working for the enemy, and sex-workers who were still plying their trade – persons who were being renewed inwardly and spiritually but whose external circumstances may never have caught up.
In the end we are all God’s children – that, I think, is what Jesus is reminding us of here. None of us are perfect sons or daughters, and those who lead the way spiritually are often the very ones we overlook or deliberately look away from.
And that is the scandal of grace!
first published in Father Dave’s weekly newsletter – September 26th, 2026
