Why Did Jesus Love the Prostitutes and the Tax Collectors?

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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.

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How Do Christians Resolve Conflict?

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Matthew 18:15-20

How do human beings deal with conflict?

From the way we act, you might conclude that human beings don’t actually deal with conflict.

Whenever a conflict rears its head, we respond in one of two ways:

(1) Fight We insist on being the wronged party and we demand restitution.

For example: Person A hears that Person B was gossiping about them to others. They become rightfully upset. Person B, however, says that they’re just telling others the truth about Person A—who does break many of God’s commandments. Both Person A and Person B are in the right and in the wrong, but neither will admit to their own fault. Eventually, Person A and Person B refuse to speak with one another because neither “will listen to common sense.”

(2) Flight We pretend not to be hurt or upset by an action to avoid conflict.

Example: Person B says something that Person A thinks is offensive. Rather than talk to Person B, Person A decides to “be the bigger man” and not tell Person B they were offended. Later, however, Person A makes several off-hand comments about Person B to other people, and asks their pastor for prayer. They never tell Person B about the problem.

Note that neither of these responses address or resolve a conflict—both are equally ineffective! How, then, do we resolve conflict?

As Christians, our immediate thought should be of Matthew 18:15-20, where Christ spells out the process of reconciliation. We should take care when we read this passage. Our natural tendency is to translate this passage into the following list of commands:

☐ “Tell [your brother] his fault” (Matthew 18:15)

☐ “Take one or two others along with you, that every charge may be established by the evidence of two or three witnesses” (Matthew 18:16)

☐ “Tell the church” (Matthew 18:17)

☐ “Let him be to you as a Gentile and a tax collector” (Matthew 18:17)

There is nothing wrong with the list (each of its commands are taken directly from the scripture). What is wrong, however, is when we hurriedly check each box after a half-hearted attempt to do the step. For example, if Person A approaches Person B, tells them what they did wrong, leaves when Person B disagrees with them, and marks the box complete, then Person A fundamentally misunderstands the scripture.

This is probably because person A is asking questions such as, “How does this scripture relate to my situation?”, “What does this scripture say about my life?” and “What does this scripture command me to do?” By asking these questions, Person A overlooks not only the context of this passage but also its purpose: revealing the character of God.

Matthew 18:15-20 fits snugly between Matthew 18:10-14 (The Parable of the Lost Sheep) and Matthew 18:21-35 (The Parable of the Unforgiving Servant) (two passages that are also frequently read out of context). When all three are read together, we see the image of a God who not only “[leaves] the ninety-nine [sheep] on the mountain to search for the one that went astray,” (Matthew 18:12-13) but who also requires us to do likewise (Matthew 18:32-33). When Jesus tells us that we are to go to our brothers in private, he does not mean to do so once and move on. He does not want us to go to our brother only seven times, “but seventy times seven” (Matthew 18:22)!

Essentially Jesus is saying: “If you have a conflict with someone, it is your responsibility to work through this conflict in private—until your brother refuses to work things through with you.” We must note two things here. First, Jesus does not present us with advice about conflict resolution; he is commanding us to follow these instructions. That means that these instructions should hold just as much weight as the Ten Commandments (or the command that encompasses all of them: “Love your neighbor as yourself” (Mark 12:31)). Refusing to follow these instructions is a sin of which we must repent.

Second, the scripture does not say, “If you have a conflict, consult a spiritual counselor, spouse, or friend.” Jesus explicitly says to speak to the person with whom you have the conflict. By taking our conflict first to a counselor, spouse, or friend, we are showing God that we trust human advice more than we trust his Holy Spirit—even if we’re just asking our pastor to pray for us. If we attempt to work the conflict out in private, we are forced to rely on the Holy Spirit to work things through, and the Holy Spirit isn’t partial to any party. In fact, the Holy Spirit has a way of convicting both parties of sins before the conflict has been resolved.

One thing we often overlook when in this passage is that Jesus never says that we are “right” or we are owed an apology. Rather, he tells us, the more important thing is for us to privately bring our hurt to the brother and for them to listen or hear us out. Jesus goes on to say that, “if two of you on earth agree about anything, it shall be done for you by my Father in heaven” (Matthew 18:19). There is no power when Christians disagree, but when we agree, all of heaven is moved.

Remember, the most important thing is not to convince our brother that we are right. Ultimately, we are fallen human beings—if we know ourselves, we know that our own self-interest shades our thoughts of right and wrong more than a little. It is not our truth that we need to confront our brother with, but the Lord’s truth: the Nicene Creed, trusted creeds, and Scripture. This is why we are instructed to bring witnesses in when our brother refuses to listen to us: not to convince the brother of our truth, but of the Lord’s truth. After all, Christians are not held accountable for testifying to your character, but God’s character.

Furthermore, even if we are right, it is better for us to lose our pride and reputation than to lose our brother or sister. As Philippians 2:3-4 says, “Do nothing out of selfish ambition or empty pride, but in humility consider others more important than yourselves.” Why should you humble yourself on behalf of your brother? Because, much like the king humbled himself to take on the debts of his servant, Jesus “humbled himself by being obedient to death—even death on a cross” so that you might be won (Philippians 2:8)—and you are expected to do likewise.

The human mantra is: Wherever two or three are gathered, there is bound to be a conflict. God never denies this; rather he chooses to be present in these very situations—if you let him. The important thing to note here is that God isn’t just another person. There isn’t you, your enemy, and God. When you and your enemy come together, God chooses to be present through both you and your enemy. Despite the tears, the screams, and the insults, God promises to be present.

God’s promise (“if two of you on earth agree about anything, it shall be done for you”) is contingent upon the verse immediately after it (“where two or three are gathered in my name, there I am, also”) (Matthew 18:20). This means that God isn’t simply rewarding two people because they have managed to agree. People can agree on all sorts of ungodly things! When we have conflicts with one another over matters of our own personal hurt, our focusing on the character of God rather than our own gain or loss is what guarantees that heaven is moved. This is always why working through conflict is important.

If we are in a conflict and think, “This conflict is hopeless and unnecessary; it is better if we just terminate the relationship,” then we are breaking Christ’s body apart. We are destroying the image of Christ for our own sake. In a way, this action is just as bad as Paul’s persecution of Christians. Jesus could just as aptly say to us, “Why are you persecuting me?”

Furthermore, when we choose not to follow these commands, we are ignoring the fact that Christ did, and continues to do, all of these things for us. As fallen human beings, we continue to fall short of his commands. Every day, we do some wrong—and yet Jesus never breaks away from us. Instead, he died for us—despite having every right to abandon us or demand recompense.

In Matthew 5:9, Jesus says, “Blessed are the peacemakers.” These peacemakers aren’t the people who “won arguments”, “held fast to ‘the truth’”, or “had no conflicts.” They are the people who continued to go back to their enemies in private, the people who considered their brother more important than their own pride, and who did all this knowing that Christ had done it all before them. Let us then be peacemakers, for it is the peacemakers who are “called children of God.”

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The End of our Reading is Eternal Life: An Excerpt from Living in the Underground Church

In the Upper Room shortly before his Gethsemane, Jesus prays to the Father. The focus of his prayer is not that his disciples would come to discern and fulfill their callings, nor that the disciples would come to fully know and do what God wants, nor that the disciples would be saved, nor that they would die to self.

Instead, Jesus’ prayer is that the character of his Father might be become known to them. Jesus calls this “eternal life”:

After Jesus said this, he looked toward heaven and prayed:

“Father, the hour has come. Glorify your Son, that your Son may glorify you. For you granted him authority over all people that he might give eternal life to all those you have given him. Now this is eternal life: that they know you, the only true God, and Jesus Christ, whom you have sent.”[5]

Jesus is praying for Jeremiah 31:34 to be fulfilled:

“They will not teach again, each man his neighbor and each man his brother, saying, ‘Know the LORD,’ for they will all know Me, from the least of them to the greatest of them,” declares the LORD, “for I will forgive their iniquity, and their sin I will remember no more.”[6]

When that Scripture is fulfilled, then “the earth will be filled with the knowledge of the glory of the LORD as the waters cover the sea.”[7]

We study the Scripture not to discern and fulfill our calling, nor to fully know and do what God wants, nor to be saved, nor to die to self. Such aspirations may seem breathtakingly holy to us, but this is only because the human heart is darkened and twisted by sin. It deceives us into believing that God urgently desires us to become nobler and more God-conscious in our egocentricity.

Instead, God seeks for us to know him. This does not come from the death of our self, but the death of our fixation on self. This is why in the Garden of Gethsemane, Christ does not pray, “Annihilate my will” or “Subsume my will into yours” or “Show me your will and give me the strength to submit to it.” Instead, he prays, “Not my will, but yours be done.”[8] God’s will is not that all rival wills be eliminated or merged into his own but that all would come to obey him from a loving, trusting obedience that flows from knowing him, as it did for Jesus.

The author of Hebrews says that Christ “learned obedience from what he suffered.”[9] This does not mean that Christ resisted suffering but ultimately yielded to an unyielding God, as though the gospel message is “Resistance is futile.” It means that in the darkest, most incomprehensible moment in history, Christ chose to embrace his Father, because he knew that his Father was trustworthy in all things. The prophet Samuel says that obedience is better than sacrifice[10]—that is, better than immolation of self. God does not want us to die. This is why the Apostle Thomas is wrong to say, “Let us also go, that we may die with him.”[11] The Apostle Peter is right to say that God is “not wanting anyone to perish, but everyone to come to repentance.”[12] If our dying to self was his goal, then our repentance could be accomplished through self-loathing, shame, and suicide. But this is not repentance. It is merely the inevitable and always fatal outcome of egocentricity. The prophet Isaiah cries, “Woe to me! I am ruined! For I am a man of unclean lips, and I live among a people of unclean lips, and my eyes have seen the King, the LORD Almighty.”[13] All who see the Lord speak in this way. If this was all the Lord desired, he could accomplish it simply by appearing to everyone as he appeared to Isaiah; baptism could then be a fleeing from his presence and drowning, and the Christian life could be an act of extended self-hatred.

Instead, the repentance God seeks is the kind Jesus has in mind when he says, “The kingdom of heaven is like treasure hidden in a field. When a man found it, he hid it again, and then in his joy went and sold all he had and bought that field.”[14] True repentance is always rooted in joy. It is rooted in the joyful discovery of the One of whom we are a fallen image. Yes, the knowledge of the extent of our fallenness can and should drive us to grief, but never to hopeless or despair or destruction. One cannot come to true repentance by hating and discarding the fallen image, or by burying it in fear that he whom we image is a hard man.[15] One can only come to true repentance by treasuring the image even in its fallenness, and by returning it joyfully, expectantly, confidently to he who is making all things new.[16]

This is why the end of all of our Scripture reading is eternal life, the knowledge of God’s character. This is why, in this present volume, commandment keeping is presented as a part of the reading process, not as its outcome or motivation. That is, we do not read the Scripture in order to know him so that we may find out what he wants us to do. Instead, we do what he wants us to do as part of our coming to know him.

Just as the disciples ask, “What kind of man is this? Even the winds and the waves obey him!”[17], there are aspects of the character of God that we can only even know to puzzle over from within the process of seeking to hear and do his word. Even this is an aspect of God’s character. Despite the many theology books that seek to systematize his character and enumerate it as a series of philosophical attributes—aseity, impassibility, omnipotence, sovereignty—God will have none of it. As R.L. Brawley notes, “God is a character whom the reader constructs out of the intersection of information, action, traits, and evaluation.”[18]

And that is how he requires it. As Isaiah says, “Truly, you are a God who hides himself, O God of Israel, the Savior.”[19] He has revealed himself fully in Christ, and yet Christ is the parable-telling God who never throws his pearls to pigs.[20] Even to his disciples who accompany him intimately for years, he asks, “Who do you say that I am?”[21] Even after he is raised from the dead—in fact, even when he is seen by John in heaven itself—the recognition of who he is and what he is like is painfully slow and error-laden. We would do well to exchange our certainty for humility; he is, after all, the God who announces his name as, “I will be who I will be.”[22]

Nevertheless, we know him as the Father of the one who commands us, “Come to me, all you who are weary and burdened, and I will give you rest.”[23] He is not burdened or wearied by the shortcomings of our knowledge but only by the arrogance, disinterest, and sin that disincline us from even his slightest correction that would enable us to know him even slightly better. If we are intent on knowing him and his character, and if we are expectant that he will be true to his word to reveal himself to and in us, and if we are willing to sacrifice all things for even one more jot or tittle of knowing him, then he will delight to grant us that desire. It is his character.[24]

Thus, before we take up the Bible to read each day, we ought to pray, “Lord, reveal your character to me.” And before we set the Bible down after reading, we ought to pray, “Lord, reveal your character to me.” And in the midst of our reading, as we are doing the word we have heard (which is a part of our reading, not a result of it), we ought to pray, “Lord, reveal your character to me.”

And throughout, we ought to take stock of what he reveals. We should not trust it to our memory, as that hardly reveals humility or good judgment. Instead, we ought to write down somewhere what we have learned. What we write down could be as simple as copying the adjectives that are in the passage of scripture we read–“The LORD, the LORD God, compassionate and gracious, slow to anger, and abounding in lovingkindness and truth; who keeps lovingkindness for thousands, who forgives iniquity, transgression and sin; yet He will by no means leave the guilty unpunished, visiting the iniquity of fathers on the children and on the grandchildren to the third and fourth generations.”[25] Or it could be as complex as writing out an extended journal reflection on who we think he is, based on what he has shown us through a process like the one outlined in this volume.

Or, like Job, it could take the form of a renunciation of what we once saw in part, now that we have received something more full;[26] it could be a repudiation of the idol we made of him in our own image; or it could be a quieting of ourselves into the worshipful, joyful silence of the eternal life of knowing God:

“I have heard of You by the hearing of the ear; But now my eye sees You; Therefore I retract, And I repent in dust and ashes.”[27]


[5] John 17:1-3, NIV.

[6] Jeremiah 31:34, NIV.

[7] Habakkuk 2:14, NIV.

[8] Luke 22:42, NIV.

[9] Hebrews 5:8, NIV.

[10] Cf. 1 Samuel 15:22.

[11] John 11:16, NIV.

[12] 2 Peter 3:9, NIV.

[13] Cf. Isaiah 6:5, NIV.

[14] Matthew 13:44, NIV.

[15] Cf. Matthew 25:24, NIV.

[16] Rev. 21:5, NIV.

[17] Matthew 8:27, NIV.

[18] R.L. Brawley, 1990. Centering on God: Method and Message in Luke-Acts (Literary Currents in Biblical Interpretation). Louisville, KY: Westminster John Knox Press, p. 111.

[19] Isaiah 45:15, ESV.

[20] Matthew 7:6, NIV.

[21] Matthew 16:15, NIV.

[22] Cf. Exodus 3:14.

[23] Matthew 11:28, NIV.

[24] Cf. Matthew 18:19; Matthew 21:22; Mark 11:24; John 14:13; John 15:7.

[25] Exodus 34:6-7, NASB.

[26] Cf. 1 Corinthians 13:12.

[27] Job 42:5-6, NASB.

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