Christ’s fifth and final discourse begins in the temple and concludes on the Mount of Olives, which affords a panoramic view of the temple complex on Mount Zion. The woes that begin this closing discourse contrast with the blessings with which the opening discourse begins. Matthew 23 begins with some words of instruction and warning to Jesus’ disciples but also to the crowds among whom were other potential followers (vv. 1–12). Jesus then shifts His attention to the scribes and Pharisees, pronouncing a series of seven woes (vv. 13–33)¹ and promising to send messengers to them who will fare no better than the prophets did or, indeed, Jesus Himself (vv. 34–36). Consequently, Jesus concludes His teaching in the temple with a lament over Jerusalem in view of its impending desolation (vv. 37–39).

Interpretation of Matthew 23

Verses 1–12

• Like the first discourse, this initial section instructs disciples of the kingdom of heaven regarding how they should relate to the teachings of the scribes and Pharisees as well as how they should relate to each other.

• Moses’ seat was a special chair in the synagogue in which the person sat while explaining the Scriptures (cf. Luke 4:20). Archeological excavations in Israel and elsewhere have revealed a number of these chairs made of stone. Some were probably made of wood and so did not survive.

• Jesus’ instruction to do “whatever” they are told by the scribes and Pharisees seems to be contradicted elsewhere in Matthew (e.g., 12:2–5; 16:11–12) and also just a few verses later (23:13, 15). But throughout this chapter Jesus is concerned more with the contradiction between theory and practice. The teachers of the law do not themselves practice everything they lay on others.

• As Jesus will proceed to explain, the “heavy burdens” (cf. Acts 15:10) are the minutely detailed rules devised by the Pharisees as to how to keep the laws of Moses, including the tithing of minute quantities of herbs (v. 23), straining out from one’s drink the smallest potential source of defilement (v. 24), as well as rules regarding Sabbath observance (12:2, 10) and ritual purifications before eating food purchased from the marketplace (15:2, 11; cf. Mark 7:3–4). The accumulated traditions had become so complicated that “none knew when their obligations were met.”²

• Several examples are given that reveal a greater concern by the scribes and Pharisees for outward appearance and external performance than inner motivations (justice, mercy, faith, and love, v. 23; Luke 11:42) which is Jesus’ real concern and which can only come through the transforming grace of the Holy Spirit working on the heart (Gal 5:22–23).

• Jesus’ public denunciation of Israel’s premier religious teachers, calling them hypocrites (vv. 13, 15, 23, 27, 29), may sound harsh to modern ears but they were no doubt spoken by Jesus in an appealing way, hoping they would see themselves and their actions as God views them, recognize their delusion, and turn to repentance.³ No doubt it also helped some to realize they were not reliable guides in religious matters.

• Three examples of their focus on outward display as symptomatic of an inner spiritual problem are given by Jesus: the widening of phylacteries and lengthening of tassels on their garments (cf. Exod 13:9) as badges of superior piety, their desiring the best seats at feasts and in the synagogue (cf. Prov 25:6–7), and coveting honorific titles (vv. 5–7). Some may wear ornamental crosses today for a similar reason but it is acceptance of the cross and all it represents in the way of self-sacrifice that signifies true faith.

• Jesus draws a clear line separating such self-serving, prideful practices from the humble, service-oriented attitude that is to characterize His followers as brothers and sisters under one Teacher (Jesus) and one heavenly Father (vv. 8–10). The parallel descriptions of the Father and Christ (the Son) place them on the same level—as divine.

2. Verses 13–33

• The seven woes are judgment oracles pronounced on the scribes and Pharisees (called “blind guides” in v. 16; cf. Matt 15:12–14), organized as a series of three pairs with the concluding woe climaxing in “this generation” (recalling Matt 12:39–45) being charged with murder and condemned to a fiery destruction.⁴

• The first two woes contrast heaven and hell: the first describes how the rejection of Jesus’ teaching shut people out of the kingdom of heaven (v. 13), while the second indicates that the teaching of the scribes and Pharisees make them “twice as much a son of hell” (v. 15)—that is, fit only for destruction in the lake of fire.

• The third and fourth woes describe the result of false teaching: spiritual blindness (cf. 2 Cor 4:4), which makes it impossible to recognize what is of most importance—the temple and the altar because God dwells there (v. 21), sanctifying the gold and the gifts brought to Him. Jesus rejects the minute casuistic distinctions made by the scribes and Pharisees because they tended to confuse people as to what was really important. While warning against leaving tithing undone (cf. Lev 27:30–33), He identifies justice, mercy, and faith as the “weightier matters of the law” (v. 23). Justice and mercy are foundational aspects of God’s character (Ps 89:14; Isa 30:18) and faith is the quality of trust in God and His ways that results in obedience (Matt 8:9–10; cf. Deut 32:20; Hab 2:4).

• Similarly, the fifth and sixth woes describe how concerns with outward piety took precedence over inner rectitude (vv. 25–28), whereas inner purity results in right outward deportment.

• The seventh woe sets forth the irony of those who revere the prophets and righteous people of a previous era while rejecting the prophetic messages of John the Baptist and Jesus, thus proving they are behaving no differently than their ancestors and, in fact, will “kill and crucify” some of those Jesus will send to them (a prophecy to which Paul apparently refers in 1 Thess 2:14–16).

• Telling them to “fill up” their guilt (v. 32) uses the word (plēroō) that frequently refers to the fulfillment of prophecy in connection with Jesus’ messianic work (e.g., Matt 5:17; 12:17; 13:35) and, thus, may allude to His own death in fulfillment of prophecy (Matt 26:31, 56).

3. Verses 34–39

• Jesus promises to send prophets, which would begin with the twelve apostles (28:19; cf. Luke 11:49). The “wise men” would be those who submit to God’s revealed wisdom (Ps 111:10) and have been instructed by Jesus (Matt 12:42; Luke 21:15; 1 Cor 1:24, 30), which includes the “scribes” He will send (cf. Matt 13:52).

• The harsh treatment His earliest followers received (Acts 5:40; 16:22–23; 21:32; 22:25; 2 Cor 11:24–25) begins to fulfill this prophecy, and the judgment Jesus alludes to with the words “all these things” points forward to the destruction of Jerusalem and the temple (24:2). The language used (“assuredly,” “will come”) underscores the certainty of the prophecy’s fulfillment.

• Jesus’ lament over Jerusalem in view of its ultimate destruction by the Romans is not unlike that of Jeremiah in connection with the Babylonian invasions (Jer 9:1; 13:17; Lam 1:16). As then, so in the time of Jesus, opposition to God’s Word through His prophets bring certain doom.

• Jesus’ desire to gather the children of Israel “as a hen” vividly conveys God’s care over His people (cf. Exod 19:4–6; Deut 32:11–12; Isa 31:5). Unfortunately, their unwillingness portends the nation’s demise as the end of their seventy weeks of probation nears its end (Dan 9:24).

• Calling the temple “your house” rather than the Father’s house (cf. Matt 21:13) indicates it has now been divinely disowned and abandoned to destruction. The term “desolate” specifies that utter destruction awaits (e.g., Lev 26:31–32; Jer 10:25; 12:11; Ezek 6:4; 33:28) and connects with Jesus’ later reference to Daniel’s prophecy (Matt 24:15) predicting the destruction of “the city and the sanctuary” (Dan 9:26).

Application of the Chapter

Some important lessons we may glean from Matthew 23 include:

1. Many times it is easier to say what should be done than to actually do it. Similarly, we may evaluate what others say and do more carefully (and strictly) than we do our own practice, whereas the example of Jesus suggests we be more merciful toward others and more careful about what we say and do since these are things, through God’s grace, we may change.

2. Only God/Christ and His Word are to be the final authority for the Christian’s faith and practice. Such honorific religious titles ascribed to human beings (as distinct from their roles or occupation) are liable to be misconstrued as giving such individuals undue authority or influence over one’s conscience and tend to undermine the principle of brotherly love and unity which should characterize the church.

3. Unlike worldly wisdom, biblical wisdom teaches humility as a sign of true greatness because it reveals that one’s life has been touched by the grace of God (Prov 3:34), surrendered to His will, and aware of the need to walk humbly before Him (Mic 6:8).

4. Making humble service a habit results in a keener awareness of the needs of others and a deeper appreciation of Jesus, the model Servant (Matt 20:28).

5. The sign of a good teacher is the ability to make complicated things clear but, unfortunately, sometimes the opposite happens: things the Bible makes clear become clouded and murky through technical distinctions, numerous qualifications, or elaborate theological discussions.

6. The human tendency is to focus on making sure what people see on the outside looks good, whereas what God sees treasured up in our hearts matters far more (Matt 6:21; 12:35; cf. Luke 16:15; Heb 4:13). Equally important to consider is whether we will have God’s blessing on what we do, or if we are determined to push ahead regardless of the warning signs He may send.

7. Ignoring God’s Word or creating avenues of interpretation to relegate unwelcome scriptures to irrelevance is to embark on a perilous path that invites divine retribution and ultimate condemnation in the judgment.