Jesus' Grace-based Judgment, part 2 (preaching resource for Oct. 22, 29 and Nov. 5 in 2023)

This post exegetes Matthew 22:15-23:39, providing context for the RCL Gospel readings on Oct. 22, 29 and Nov. 5 in 2023 (21st, 22nd and 23rd Sundays after Pentecost). This exegesis draws on commentary from Robert F Capon ("Kingdom, Grace, Judgment"), RT France ("New Bible Commentary"), and Louis Barbieri ("Bible Knowledge Commentary"). This post is part of a four-part series; to access the other parts, click a number: 134.


Last time we looked at the first part of the Holy Week confrontations between Jesus and the Jewish religious establishment. We’ll now look at additional ones. Throughout, Jesus uses these confrontations to reveal more about his identity as the Messiah, the Son of God; and about the radical nature of the grace and judgment that comes in and through him.

"Woe Unto You Scribes and Pharisees" by Tissot
(public domain via Wikimedia Commons)

Confronting the Jewish religious establishment (22:15-22:46)

The Jewish religious leaders continue to try to entrap and thus condemn Jesus. Jesus turns their attempts back on them. In rejecting Jesus, they are judged.

Concerning taxation (22:15-22)

15 Then the Pharisees went out and laid plans to trap him in his words. 16 They sent their disciples to him along with the Herodians. "Teacher," they said, "we know you are a man of integrity and that you teach the way of God in accordance with the truth. You aren't swayed by men, because you pay no attention to who they are. 17 Tell us then, what is your opinion? Is it right to pay taxes to Caesar or not?" 

18 But Jesus, knowing their evil intent, said, "You hypocrites, why are you trying to trap me? 19 Show me the coin used for paying the tax." They brought him a denarius, 20 and he asked them, "Whose portrait is this? And whose inscription?" 21 "Caesar's," they replied. Then he said to them, "Give to Caesar what is Caesar's, and to God what is God's." 22 When they heard this, they were amazed. So they left him and went away.

The religious leaders of Israel now have one goal: to get rid of Jesus. They will do so using any means possible, even if it means cooperating with lifelong enemies. The Pharisees are the purists of the nation who oppose Rome and all attempts by Rome to intrude into the Jewish way of life. But the Herodians actively support the rule of Herod the Great and favor making changes with the times as dictated by Rome. But those issues are less important to them now than the pressing issue of getting rid of Jesus. So they send a delegation to try to trick Jesus. Their scheme concerns the Roman poll-tax, which is fiercely resented by all patriotic Jews as a symbol of their political subjection. Some 25 years earlier a major revolt against this tax had been sparked by a Galilean popular leader, Judas (see Acts 5:37), from whom the Jewish group called the Zealots took its inspiration. 

This inquiry of Jesus is thus a loaded question: to support the tax is to be unpatriotic, while to oppose it is politically dangerous (especially for a Galilean popular leader now visiting Jerusalem at Passover). In getting them to show him a denarius, Jesus craftily turns the table and exposes them as hypocrites, since no patriotic Jew should have been carrying this coin, with its ‘idolatrous’ portrait of the emperor and its inscription giving him the title ‘Son of God’. If they are using Caesar’s money, let them pay his poll-tax! Score one for Jesus.

Concerning resurrection (22:23-33)

23 That same day the Sadducees, who say there is no resurrection, came to him with a question. 24 "Teacher," they said, "Moses told us that if a man dies without having children, his brother must marry the widow and have children for him. 25 Now there were seven brothers among us. The first one married and died, and since he had no children, he left his wife to his brother. 26 The same thing happened to the second and third brother, right on down to the seventh. 27 Finally, the woman died. 28 Now then, at the resurrection, whose wife will she be of the seven, since all of them were married to her?" 

29 Jesus replied, "You are in error because you do not know the Scriptures or the power of God. 30 At the resurrection people will neither marry nor be given in marriage; they will be like the angels in heaven. 31 But about the resurrection of the dead-- have you not read what God said to you, 32 'I am the God of Abraham, the God of Isaac, and the God of Jacob'? He is not the God of the dead but of the living." 

33 When the crowds heard this, they were astonished at his teaching.

Unlike the Pharisees, who initiated the last confrontation with Jesus, the Sadducees do not believe in a life after death, since they think it is not taught in the Torah (the five books of Moses), which is the only Scripture they accept as authoritative. They see this as an area where Jesus’ teaching can be made to look ridiculous. Thus their ‘question’, based on the levirate law of Deut. 25:5–6, is not a serious enquiry but an attempt to poke fun at the idea of resurrection. It does, however, raise a real pastoral issue for those who have been married more than once. Jesus’ reply is two-fold. On the specific issue raised, he points out (v30) that resurrection life is not a mere continuation of life on earth. On the more fundamental question of resurrection itself, Jesus finds a basis for this belief even in the Sadducees’ own Scriptures, the Torah (vv31–32). For God to describe himself in relation to the patriarchs who died long before (Ex. 3:6) implies that there is a continuing relationship. God’s covenant with his people is not frustrated by death.

Concerning law (22:34-40) 

34 Hearing that Jesus had silenced the Sadducees, the Pharisees got together. 35 One of them, an expert in the law, tested him with this question: 36 "Teacher, which is the greatest commandment in the Law?" 37 Jesus replied: "'Love the Lord your God with all your heart and with all your soul and with all your mind.' 38 This is the first and greatest commandment. 39 And the second is like it: 'Love your neighbor as yourself.' 40 All the Law and the Prophets hang on these two commandments."

Not to be outdone, the Pharisees try again to entrap Jesus, exposing him as the Law-breaker they imagine him to be. But once again, Jesus turns the table and traps them. It was common at that time for rabbis to quote Deut 6:5 and Lev 19:18 in discussing ethics. Jesus follows suit, but adds something new by putting these two verses together and noting that the love to which they speak is the essence of the Torah. The implication is that they, not he, are the law breakers, for they completely overlook the love that Jesus has come to embody and thus reveal. 

Concerning Messiah’s identity (22:41-46) 

41 While the Pharisees were gathered together, Jesus asked them, 42 "What do you think about the Christ? Whose son is he?" "The son of David," they replied. 43 He said to them, "How is it then that David, speaking by the Spirit, calls him 'Lord'? For he says, 44 "'The Lord said to my Lord: "Sit at my right hand until I put your enemies under your feet." ' 45 If then David calls him 'Lord,' how can he be his son?" 46 No one could say a word in reply, and from that day on no one dared to ask him any more questions.

Jesus now goes on the offensive and questions the Pharisees. On the surface, his question sounds like an academic one: Is Son of David a proper title for the Messiah (the Christ)? Jesus has repeatedly been hailed in public with this title (see Matt. 21:9, 15–16). Thus, it is Jesus’ own status that is at issue here. Son of David is a traditional Messianic title at this time, and one which not only occurs frequently in Matthew’s narrative but forms the basis of the presentation of Jesus as the Messiah in chapter 1. 

Jesus is not trying to undermine the idea that the Messiah is a human descended from David, but he is showing from David’s own testimony (Psa 110:1) that the Messiah is both human and divine. This text is used again in 26:64 to claim for Jesus a superhuman authority. Thus Jesus is warning the Pharisees against judging his mission in traditional terms. Far from being enthroned in Jerusalem as a king like David, he will soon be rejected by his people. But even then, on the cross, he will be recognized at last not as merely a son of David (the title does not occur again), but also as the ‘Son of God’ (Matt. 27:54). Jesus is revealing himself to be both human and divine. In this revelation there is a very stern warning against those who would reject him. The theological complexities of this discussion are more than the Pharisees can handle, and no one…dared answer his question or debate points of practice or theology with him. All his opponents have now been silenced, including the chief priests and elders (Matt. 21:23-27), the Pharisees and the Herodians together (vv15-22), the Sadducees (vv23-33), and the Pharisees (vv34-36).

Confronting the Jewish religious establishment (23:1-39)

Up to this point, Jesus’ warnings to the Jewish religious leaders have been rather indirect. But now he targets them head on, accusing them as blind guides and blind fools. And yet, his passionate diatribe concludes with great pity for these deceived people. Once again, God’s judgment is shown to be grace-based.

Warning (23:1-12) 

1 Then Jesus said to the crowds and to his disciples: 2 "The teachers of the law and the Pharisees sit in Moses' seat. 3 So you must obey them and do everything they tell you. But do not do what they do, for they do not practice what they preach. 4 They tie up heavy loads and put them on men's shoulders, but they themselves are not willing to lift a finger to move them. 5 Everything they do is done for men to see: They make their phylacteries wide and the tassels on their garments long; 6 they love the place of honor at banquets and the most important seats in the synagogues; 7 they love to be greeted in the marketplaces and to have men call them 'Rabbi.' 8 But you are not to be called 'Rabbi,' for you have only one Master and you are all brothers. 9 And do not call anyone on earth 'father,' for you have one Father, and he is in heaven. 10 Nor are you to be called 'teacher,' for you have one Teacher, the Christ. 11 The greatest among you will be your servant. 12 For whoever exalts himself will be humbled, and whoever humbles himself will be exalted.”

Jesus here addresses the crowd and his disciples. He is targeting the scribes (teachers of the law), and the Pharisees. Though these officials have legitimate authority (they sit in Moses’ seat), they are abusing that authority by insisting on a huge and growing list of rules and regulations that puts religion above God’s will. In doing so, they are hypocrites, for (as noted in vv2-7) they dishonor God in their unconcern with the problems that their teaching creates for ordinary people (the heavy loads of v4 refer to the demands which scribal legislation makes on daily living; see Matt. 11:28–30). In contrast (vv8–12), the disciples are not to seek after status but take the low places in order to truly serve others. This last section picks up the theme of Matt. 20:25–28, but whereas there the contrast is with ‘the rulers of the Gentiles’, here it is with the supposed leaders of the people of God (the Jews).

Woes (23:13-36) 

Jesus now turns to the scribes and Pharisees and pronounces seven woes:

13 "Woe to you, teachers of the law and Pharisees, you hypocrites! You shut the kingdom of heaven in men's faces. You yourselves do not enter, nor will you let those enter who are trying to. 14 ....  

15 "Woe to you, teachers of the law and Pharisees, you hypocrites! You travel over land and sea to win a single convert, and when he becomes one, you make him twice as much a son of hell as you are. 

16 "Woe to you, blind guides! You say, 'If anyone swears by the temple, it means nothing; but if anyone swears by the gold of the temple, he is bound by his oath.' 17 You blind fools! Which is greater: the gold, or the temple that makes the gold sacred? 18 You also say, 'If anyone swears by the altar, it means nothing; but if anyone swears by the gift on it, he is bound by his oath.' 19 You blind men! Which is greater: the gift, or the altar that makes the gift sacred? 20 Therefore, he who swears by the altar swears by it and by everything on it. 21 And he who swears by the temple swears by it and by the one who dwells in it. 22 And he who swears by heaven swears by God's throne and by the one who sits on it. 

23 "Woe to you, teachers of the law and Pharisees, you hypocrites! You give a tenth of your spices-- mint, dill and cummin. But you have neglected the more important matters of the law-- justice, mercy and faithfulness. You should have practiced the latter, without neglecting the former. 24 You blind guides! You strain out a gnat but swallow a camel. 

25 "Woe to you, teachers of the law and Pharisees, you hypocrites! You clean the outside of the cup and dish, but inside they are full of greed and self-indulgence. 26 Blind Pharisee! First clean the inside of the cup and dish, and then the outside also will be clean. 

27 "Woe to you, teachers of the law and Pharisees, you hypocrites! You are like whitewashed tombs, which look beautiful on the outside but on the inside are full of dead men's bones and everything unclean. 28 In the same way, on the outside you appear to people as righteous but on the inside you are full of hypocrisy and wickedness. 

29 "Woe to you, teachers of the law and Pharisees, you hypocrites! You build tombs for the prophets and decorate the graves of the righteous. 30 And you say, 'If we had lived in the days of our forefathers, we would not have taken part with them in shedding the blood of the prophets.' 31 So you testify against yourselves that you are the descendants of those who murdered the prophets. 32 Fill up, then, the measure of the sin of your forefathers! 33 "You snakes! You brood of vipers! How will you escape being condemned to hell? 34 Therefore I am sending you prophets and wise men and teachers. Some of them you will kill and crucify; others you will flog in your synagogues and pursue from town to town. 35 And so upon you will come all the righteous blood that has been shed on earth, from the blood of righteous Abel to the blood of Zechariah son of Berekiah, whom you murdered between the temple and the altar. 36 I tell you the truth, all this will come upon this generation.

With these seven woes, Jesus denounces the Jewish religious leaders, and sets the scene for his prediction of Jerusalem’s destruction (which ends this chapter).

1) The first woe (v13) describes their approach to religion as a hindrance to those who really want to please God. 

2) The second woe (v15) recognizes that they are keen to win converts (to Judaism). The problem is that their religious system makes people worse rather than better (son of hell means one who belongs there; compare this to sons of the kingdom in Matt. 8:12). 

3) The third woe (vv16-22), like the rest, gives an example of how perverted their religious values are. The example here is of using oaths in a legalistic way. Jesus has already shown that oaths are unnecessary (Matt. 5:33–37). Here he adds that attempts to distinguish between more and less ‘serious’ oaths are futile, since all ultimately go back to God as the one whose name is invoked.

4) The fourth woe (vv23–24) does not condemn tithing as such, but points out the absurd lack of proportion involved (strain out a gnat but swallow a camel!) when they go into meticulous detail over tithing garden herbs, yet overlook justice, mercy and faithfulness. The prophets often protested similarly against a ritualistic religion which forgets the things that really matter (see Micah 6:6–8).

5-6) The fifth and sixth woes (vv25–26, 27–28) similarly deal with the priority of inward purity over outward appearance. This is the issue which Jesus has already raised in Matt. 15:11, 17–20 in connection with ritual hand-washing. The reference in v27 may be to ossuaries, the small chests into which human bones are placed, and which were often given a lime plaster covering to make them appear beautiful.

7)  The seventh woe (vv29–31) leads into a devastating paragraph declaring that Israel’s rebellion against God has reached its culmination in this generation (see Matt. 12:38–45). Thus judgment, which has for long been brewing, is about to fall on them. It is easy, with the passage of time, for the people to distance themselves from the way their forefathers treated the prophets and the righteous and to build monuments in their honor, but in fact nothing has changed. They are still descendants of these forefathers, in attitude as well as in genealogy, as their treatment of God’s messengers in their own day shows (v34). So as they fill up the measure of the sins of Israel, the climax has come, and the righteous blood of all God’s spokesmen in the past will come upon this present generation (see Matt. 27:25 for this way of expressing responsibility for death and liability to punishment).

Grace-based judgment (23:37-39) 

37 "O Jerusalem, Jerusalem, you who kill the prophets and stone those sent to you, how often I have longed to gather your children together, as a hen gathers her chicks under her wings, but you were not willing. 38 Look, your house is left to you desolate. 39 For I tell you, you will not see me again until you say, 'Blessed is he who comes in the name of the Lord.'"

The seventh woe widened the scope from the hypocrisy of the scribes and Pharisees to the guilt of all Israel in rejecting God’s messengers (including Jesus). The inevitable conclusion is now drawn—Jerusalem, which should have known better, will fall. And yet in the midst of this pronouncement of severe judgment, Jesus expresses his own sorrow and pity (note the frequent use of the word I in this section). Doing so brings the conversation back to the reality of Jesus’ own, soon-coming death and resurrection—the basis on which these people will ultimately be saved, rather than forever destroyed. However, the judgment that flows from their present rejection of Jesus is coming quickly. Your house (the temple in Jerusalem) will not only be destroyed (see Matt. 24:2), but left desolate—abandoned by God. This had happened many years earlier when Jeremiah’s appeal was refused (v38 echoes Jer 12:7). Jesus does not say when the time will be when they will see him again. The Greek for until is deliberately indefinite. However, when he does return, he anticipates that their reaction to him will be quite different, and thus this section on white-hot judgment ends with a note of hope. 


In revealing more about God’s judgment, Jesus points out that the sorrow and death that judgment brings immediately is followed by resurrection to new life. Once again, Jesus shows in dramatic fashion that God’s judgment and justice are expressions of his love—a love seen supremely and ultimately in the person and work of God’s own Son, Jesus Christ. 

God’s judgment comes through, and only through Jesus, our Savior. Thus, God’s judgment is based in his grace—it is judgment that leads not to condemnation, but through death and resurrection to forgiveness and new life. How can that be? God, in the person of his incarnate Son Jesus Christ, has taken upon himself our sin, has died our death, and out of that death (remaining united to us through permanent incarnation) has ushered us, via his resurrection and ascension, into new life. This is a finished work—a ‘done deal.’ The only remaining question for us personally is this: Do we trust Jesus to be our death to sin and our new, resurrected-ascended human life?