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Matthew 21:23-32

You’ve done it again.

After an intense bout with temptation, you’ve surrendered. You’ve eaten that extra slice of cake. You’ve stretched your budget to buy that new phone. You’ve responded to your spouse out of anger rather than understanding.

Now you’re caught in the throes of guilt—what do you do?

Often, our tendency is to repent with a promise: “I’ll try harder this time!” However, our well-intended promises are rarely strong enough to overcome the harsh cycle of sin and repentance. Within a few months, days, or even hours, we find ourselves doing the very same thing again—why?

Matthew 21:23-32 sheds light on this phenomenon.

The scripture begins with the chief priests and elders posing a question to Jesus: “By what authority are you doing these things, and who gave you this authority?” (Matthew 21:25)

This question is so abstract and theoretical that it is easy to lose interest in it altogether. After all, we know that Christ’s authority comes from his Father. What we don’t know, however, is how this passage could possibly tie into our lives. And so we often glaze over this scripture, choosing instead to engage with the parable that comes soon after. By doing so, however, we are overlooking the common theme which not only weaves both passages into each other, but also into the entirety of scripture.

At the heart of this exchange is not a masterfully woven theoretical argument, but a practical castigation which Christ comes back to time and time again: “Truly, I say to you, the tax collectors and the prostitutes enter the kingdom of God before you” (Matthew 21:31).

Throughout scripture, Jesus shows kindness and favor to tax collectors and prostitutes. He is merciful to the adulteress from John 8:1-11, reclines with Levi in Mark 2:13-17, and, in Luke 19:1-10, inspires Zaccheus to give half his goods to the poor. This kindness, however, is interpreted as a weakness (or even a transgression) by the religious leaders. When a prostitute comes to anoint Jesus’ feet with perfume, for example, the religious leaders sneer, “If this man truly were a prophet, he would know that the woman touching him was a sinner” (Luke 7:39).

When met with their scorn, Jesus responds by reminding them of their place—behind the prostitutes and tax collectors. This is not to say that there is something inherently redemptive about prostitution or tax collecting—both “vocations” are, by definition, antithetical to Christ’s message—but it is to say that there is a deeper reasoning behind Christ’s claim.

During Christ’s time, prostitutes and tax collectors were considered to be the most sinful of sinners. A prostitute capitalized on the basest and most primitive of human desires—lust—to make a living. Not only did prostitutes immerse themselves in sin, but, some thought, that their very presence allured others along this dark path as well. (Obviously, this was a simplistic and incorrect take on things—prostitution is closely tied to poverty and oppression—but it was also the prevailing opinion of the time.)

Tax collectors were also thought to have exchanged their morals for money. True to their name, these were individuals that were responsible for collecting taxes for the government. However, tax collectors were not paid by the government. Everyone understood that a tax collector was to earn his living by overcharging citizens for their taxes. Tax collectors, then, were thought to be liars and thieves, caring more about money than righteousness, justice, or their fellow human beings.

Despite their differences, prostitutes and tax collectors had one thing in common: they could not hide the fact that they were sinners. Everyone would notice the callers moving to and from a prostitute’s house. Everyone would have taxes taken from them by a tax collector at another point. Due to the nature of their job, prostitutes and tax collectors could not hide their true nature from others or, more importantly, from themselves.

This, Jesus explains, is the wonderful thing about tax collectors and prostitutes.

“Blessed are the poor in spirit,” Jesus says in the Sermon on the Mount, “for theirs is the kingdom of God” (Matthew 5:3). In other words: Blessed are the people who know they are not good, who know they have done wrong, and who cannot hide either of these facts from others and themselves. It is these people who will inherit the kingdom of God.

Knowing you’re a sinner and being fine with it, however, is a different situation altogether. Note that the prostitutes and tax collectors that Jesus interacts with are either actively seeking him (Luke 15:1) or overjoyed by his presence (Luke 19:5-6). These are not people who are satisfied with their lot in life, but who see through Jesus, and John before him, a way to become something more than themselves. This is perhaps best evidenced through Zaccheus’ act of repentance: “Look Lord! Here and now I give half of my possessions to the poor, and if I have cheated anybody out of anything, I will pay back four times the amount” (Luke 19:8). Even the adulteress saved by Christ’s word is freed with the instruction to “go and sin no more” (John 8:11). These are not sinners who are content with their sin.

The religious leaders—and the religious individuals—who confront Jesus, on the other hand, are sinners who are content with their sins.  By and large, this contentment is caused by a refusal to acknowledge a sinful nature in the first place (Matthew 21:31-33).

Religious people (whether it be the Jews of Christ’s day or the Christians of our own) are keenly aware of sin—often, this is what drives us to religion in the first place—but we often have a nasty habit of seeing sin more clearly in others than in ourselves. We heap curses and hellfire upon the prostitutes and tax collectors of our time, without giving serious consideration to the prostitutes and tax collectors of our own hearts.

When we do consider our own sins, it is often in the light of willpower: “I’ve done some terrible things, but I’ll work harder to fix them; there’s no reason to tell anyone else what I’ve done.” Unfortunately, according to Jesus, this is the worst place to be in. If we are working at overcoming our sins—the very same sins that Christ died to wash clean—then we are showing that we trust ourselves instead of Christ, and he can give us nothing but the space to enact our own rituals and acts of limited might.

This is why our well-intended promises can only guide us back to sin’s doorstep.

In order to enter the Kingdom of God, we must become people who do not deny, hide, or desire our evil nature. These are not attitudes that we can bestow upon ourselves, but are gifts given by God. We must come before him in prayer and ask that he make us more like prostitutes and tax collectors, and less like religious leaders. Once we humble ourselves, realizing that we are worms and not men (Psalm 22:6), we will be blessed, and the Kingdom of God will be given to us.