In Matthew 21:23-27, a tense confrontation unfolds in the temple courts of Jerusalem, where the chief priests and elders challenge Jesus’ authority to teach, perform miracles, and disrupt temple activities. This passage, set during Jesus’ final week before his crucifixion, follows his triumphal entry as the “Son of David” (Matt. 21:9) and his bold cleansing of the temple (21:12-17), actions that provoked the religious elite. By questioning, “By what authority are you doing these things, and who gave you this authority?” (21:23, NIV), the leaders aim to undermine Jesus’ legitimacy, exposing their own hypocrisy and spiritual blindness. Jesus’ response—a counter-question about the origin of John the Baptist’s baptism—reveals the divine source of his authority and aligns his ministry with John’s prophetic mission. This article harmonizes the doctrinal continuity between John and Jesus, demonstrating how Jesus’ teachings fulfill and extend John’s message of repentance, judgment, and messianic hope.

Literarily, Matthew 21:23-27 is part of a series of conflict stories (Matt. 21–23) that contrast Jesus’ divine authority with the leaders’ human-derived power. Paralleled in Mark 11:27-33 and Luke 20:1-8, the passage employs a rabbinic debate style, with Jesus’ counter-question serving as both defense and indictment. R.T. France highlights Matthew’s emphasis on the Kingdom of God, noting that this confrontation sets the stage for Jesus’ parables (e.g., 21:28-46), which critique Israel’s unfaithfulness and anticipate the inclusion of Gentiles in God’s plan.

Exegesis and Doctrinal Continuity

The chief priests and elders’ question is not a genuine inquiry but an attempt to discredit Jesus, who lacked formal rabbinic credentials or Sanhedrin approval. Their hypocrisy is evident, as their own authority often stemmed from political alliances rather than divine appointment. Jesus responds strategically: “I will also ask you one question. If you answer me, I will tell you by what authority I am doing these things. John’s baptism—where did it come from? Was it from heaven, or of human origin?” (21:24-25). Far from evading the issue, Jesus’ question establishes his authority by linking his ministry to John the Baptist’s divinely ordained mission.

The doctrinal alignment between John and Jesus is central to understanding this passage. John’s ministry, as a forerunner to the Messiah, prepared the way through a message of repentance and eschatological urgency. Jesus’ teachings build upon and fulfill this foundation, as evidenced by the following parallels:

Repentance and the Kingdom: Both John and Jesus preached, “Repent, for the kingdom of heaven is at hand” (Matt. 3:2; 4:17), signaling the imminent arrival of God’s reign and calling for spiritual renewal.

Messianic Preparation and Fulfillment: John’s role as the voice “preparing the way” (Matt. 3:3; Isa. 40:3; Matt. 11:10; Mal. 3:1) pointed to Jesus as the Messiah who would bring salvation and judgment. Jesus fulfilled this by proclaiming himself as the one coming “on the clouds” to judge and redeem in the first-century generation (Matt. 16:27-28; 24:27-34; cf. Isa. 40:10; Mal. 4:1-2).

Imminent Judgment: John warned of a “wrath about to come” upon Israel’s leaders (Matt. 3:7, GNT), while Jesus prophesied a “wrath” against “this people” within his generation, culminating in the AD 70 destruction of Jerusalem (Luke 21:23-32).

Eschatological Harvest: John depicted judgment as an imminent harvest (Matt. 3:12), a metaphor Jesus extended to describe the end of the old covenant age (Matt. 13:39-43), realized in AD 70 when the temple system collapsed and He separated the righteous from the wicked.

Baptism with Spirit and Fire: John testified that Jesus would baptize with the Holy Spirit and fire (Matt. 3:11). Jesus fulfilled this by sending the Spirit at Pentecost (Acts 1:5; 2:1-4) and, in judgment, allowing Jerusalem’s destruction by Roman forces, symbolized as fire (Matt. 22:7).

Atonement and Sacrifice: John declared Jesus the “Lamb of God who takes away the sin of the world” (John 1:29). Jesus presented himself as the Passover Lamb, laying down his life for his sheep (Matt. 26:26-28; John 10:11).

Divine Testimony and Authority: At Jesus’ baptism, the Father’s voice proclaimed, “This is my beloved Son, with whom I am well pleased” (Matt. 3:17), affirming Jesus’ divine authority. Jesus later claimed unity with the Father (John 8:18ff.), grounding his exousia in divine endorsement, which John’s ministry authenticated.

By invoking John’s baptism, Jesus forces the leaders into a dilemma. Admitting John’s divine authority would validate Jesus’ ministry, as John testified to him as the Messiah. Denying it would alienate the crowd, who revered John as a prophet (21:26). Their response, “We don’t know” (21:27), reveals their cowardice and refusal to engage with truth, prompting Jesus to withhold a direct answer: “Neither will I tell you by what authority I am doing these things.” As John Calvin notes, Jesus’ appeal to John is sufficient proof of his divine commission, exposing the leaders’ hypocrisy and affirming his authority from the Father.

Theological Themes

Matthew 21:23-27 underscores several theological themes, harmonizing scholarly insights with the emphasis on John’s legacy:

Divine Authority: Jesus’ authority, rooted in the Father and affirmed by John, contrasts with the leaders’ human-derived power. Jesus’ question implies a shared divine source with John, challenging the leaders to acknowledge God’s work.

Hypocrisy and Rejection: The leaders’ refusal to answer reflects their spiritual blindness, a recurring motif in Matthew (e.g., 23:13-36). R.T. France sees this as part of Matthew’s critique of Israel’s leadership, preparing for the transfer of the Kingdom to a new people (21:43).

John’s Prophetic Role: John’s ministry bridges the Old Testament prophets and Jesus’ messianic mission. His baptism, a call to repentance, authenticates Jesus’ authority, as Heinrich Meyer observes.

Eschatological Fulfillment: The passage’s focus on judgment aligns with the AD 70 destruction of Jerusalem, fulfilling John’s and Jesus’ urgency and warnings. 

Matthew 21:23-27 is a pivotal moment in Jesus’ ministry, where his divine authority, rooted in the Father and affirmed by John the Baptist, confronts human hypocrisy. The doctrinal continuity between John and Jesus—centered on repentance, judgment, and messianic hope—underscores Jesus’ fulfillment of John’s prophetic mission, culminating in the AD 70 judgment. By harmonizing scholarly exegesis with a focused analysis of this continuity, this passage challenges readers to discern true authority and respond to God’s Kingdom call.

Jesus will now connect a parable of response of the leaders and their unbelief to John and Jesus’ ministry with those who were believing their message was from God or heaven.

The Parable of the Two Sons: A Continuation of Jesus’ Indictment (Matt. 21:28-32)

Immediately following the confrontation over his authority (Matt. 21:23-27), Jesus transitions to the Parable of the Two Sons (Matt. 21:28-32), a pointed illustration that builds on the leaders’ refusal to acknowledge John’s divine mission and, by extension, Jesus’ own authority. This parable flows seamlessly from the preceding dialogue, intensifying Jesus’ critique of the chief priests and elders while affirming the doctrinal unity between his ministry and John’s. By presenting a story of obedience and disobedience, Jesus exposes the leaders’ hypocrisy, underscores the necessity of repentance, and anticipates the inclusion of the marginalized in God’s Kingdom—a theme rooted in John’s call and fulfilled in Jesus’ mission.

Narrative and Thematic Continuity

The Parable of the Two Sons is the first of three parables (followed by the Parable of the Tenants, 21:33-46, and the Wedding Feast, 22:1-14) that Jesus delivers in response to the leaders’ challenge to his authority. Literarily, it serves as a direct application of the confrontation in 21:23-27, where the leaders’ refusal to answer Jesus’ question about John’s baptism reveals their spiritual cowardice and rejection of God’s messengers. The parable’s setting—a vineyard, a common biblical symbol for Israel (Isa. 5:1-7)—and its focus on obedience align with the eschatological and covenantal themes of Matthew 21, particularly the transfer of the Kingdom from unfaithful Israel to a new people (21:43).

In the parable, a father asks his two sons to work in his vineyard. The first son refuses but later repents and obeys, while the second son agrees but fails to act (21:28-30). Jesus poses the question, “Which of the two did what his father wanted?” (21:31), to which the leaders respond, “The first.” Jesus then delivers a stinging rebuke: “Truly I tell you, the tax collectors and the prostitutes are entering the kingdom of God ahead of you. For John came to you to show you the way of righteousness, and you did not believe him, but the tax collectors and the prostitutes did. And even after you saw this, you did not repent and believe him” (21:31-32, NIV).

Exegesis of the Parable

The parable’s meaning is clear in light of the preceding confrontation. The first son represents the tax collectors and sinners who initially rejected God’s call but repented in response to John’s preaching, embracing the “way of righteousness” (21:32). The second son symbolizes the religious leaders who outwardly professed allegiance to God but failed to act on John’s message or recognize Jesus as the Messiah. By invoking John’s ministry, Jesus reinforces the continuity between their messages: John’s call to repentance (Matt. 3:2) is fulfilled in Jesus’ proclamation of the Kingdom (Matt. 4:17), and both demand genuine obedience over empty promises.

The phrase “way of righteousness” (21:32) is significant, echoing John’s role as a prophet who prepared Israel for the Messiah through repentance and moral renewal (cf. Matt. 3:3; Isa. 40:3). The leaders’ failure to believe John mirrors their rejection of Jesus, as both ministries required a heart-level response to God’s authority. The parable underscores Matthew’s theme of “reversal,” where the outcasts—tax collectors and prostitutes—enter the Kingdom ahead of the self-righteous elite, fulfilling John’s and Jesus’ warnings of judgment on unrepentant Israel (Matt. 3:7-12; 23:13-36). 

Doctrinal and Eschatological Connections

The Parable of the Two Sons extends the doctrinal parallels outlined in Matthew 21:23-27, particularly the themes of repentance, judgment, and divine authority:

Repentance and Kingdom Access: Just as John and Jesus preached repentance as the prerequisite for entering the Kingdom (Matt. 3:2; 4:17), the parable contrasts genuine repentance (the first son) with hypocritical profession (the second son). The inclusion of sinners reflects John’s success in reaching the marginalized (Matt. 3:5-6) and Jesus’ mission to the lost (Matt. 9:12-13), culminating in the new covenant community post-AD 70.

Judgment on Unfaithful Israel: The parable’s indictment of the leaders aligns with John’s warning of imminent wrath (Matt. 3:7) and Jesus’ prophecy of Jerusalem’s destruction (Matt. 24:1-34). The leaders’ failure to repent ensures their exclusion from the Kingdom, fulfilled in the AD 70 judgment when the old covenant system was dismantled.

Divine Authority Affirmed: By linking the parable to John’s ministry, Jesus reaffirms that his authority, like John’s, comes from God. The leaders’ rejection of both prophets underscores their rebellion against divine revelation, a theme that resonates with the eschatological harvest imagery of John (Matt. 3:12) and Jesus (Matt. 13:39-43).

Inclusion of the Marginalized: The parable’s elevation of tax collectors and prostitutes fulfills John’s preparatory role (Mal. 3:1) and Jesus’ messianic mission to redeem the outcasts (Isa. 61:1-2; Matt. 11:5). This anticipates the Gentile inclusion in the Kingdom (Matt. 21:43), realized after AD 70 as the gospel spread beyond Israel.

Theological and Eschatological Significance

The Parable of the Two Sons serves as a narrative bridge between the confrontation in 21:23-27 and the subsequent parables, which further develop the theme of Israel’s unfaithfulness and the Kingdom’s transfer. Theologically, it reinforces the necessity of repentance as the response to divine authority, a message central to both John and Jesus. Eschatologically, it points to the AD 70 judgment as the culmination of Israel’s rejection of God’s messengers, fulfilling the warnings of both prophets. The parable’s focus on John’s “way of righteousness” ties Jesus’ authority to the prophetic tradition, exposing the leaders’ hypocrisy and heralding the inclusion of the repentant in God’s redemptive plan.

Here is a chart demonstrating parallels between John’s authoritative teaching and Jesus’ and how the parable of the two sons is contextually connected:

Conclusion

Matthew 21:23-27 and the Parable of the Two Sons (21:28-32) form a cohesive unit, where Jesus’ divine authority, rooted in the Father and affirmed by John, confronts human hypocrisy and calls for genuine repentance. The confrontation exposes the leaders’ refusal to acknowledge God’s messengers, while the parable illustrates the consequences of their disobedience, contrasting it with the repentance of sinners. Together, these passages underscore the doctrinal continuity between John and Jesus—centered on repentance, judgment, and messianic hope—culminating in the AD 70 judgment and the inclusion of the marginalized in God’s Kingdom.

Study Questions for Matthew 21:23-32: Jesus’ Authority, the Doctrine of John the Baptist, and the Parable of the Two Sons

1. Contextual Understanding: How do the events preceding Matthew 21:23-27 (e.g., the triumphal entry and temple cleansing in Matt. 21:1-17) set the stage for the chief priests and elders’ challenge to Jesus’ authority? Why might these actions have threatened the religious leaders?
2. Exegetical Analysis: Why do the chief priests and elders question Jesus’ authority (Matt. 21:23), and what does their question reveal about their motives and spiritual condition? How does their lack of divine appointment contrast with Jesus’ authority?
3. Jesus’ Rhetorical Strategy: In Matt. 21:24-25, Jesus responds with a counter-question about John’s baptism. How does this approach demonstrate his wisdom, and why is it effective in exposing the leaders’ hypocrisy?
4. Doctrinal Continuity: The article lists eight parallels between John the Baptist’s and Jesus’ teachings (e.g., repentance, imminent judgment, obedience). Choose one of these parallels and explain how Jesus fulfills John’s message, citing relevant scriptures from the chart.
5. Eschatological Significance: How does the article connect John’s and Jesus’ warnings of judgment to the AD 70 destruction of Jerusalem? What does this fulfillment reveal about the urgency of their messages in the first-century context?
6. Theological Theme of Authority: How does the article demonstrate that Jesus’ authority is divinely sourced, particularly through John’s testimony and the Father’s declaration (Matt. 3:17)? How does this contrast with the human-derived authority of the religious leaders?
7. Hypocrisy and Spiritual Blindness: The religious leaders respond, “We don’t know” (Matt. 21:27), to Jesus’ question. What does this response indicate about their spiritual condition, and how does it relate to Matthew’s broader critique of Israel’s leadership (e.g., Matt. 23:13-36)?
8. John’s Prophetic Role: According to the article, how does John the Baptist serve as a bridge between Old Testament prophets and Jesus’ messianic mission? Provide examples from the chart (e.g., messianic preparation, divine testimony) to support your answer.
9. Contemporary Application: The article suggests that Matthew 21:23-27 challenges readers to discern true authority. How can modern believers apply this principle when evaluating spiritual or societal leaders? Jesus didn’t go through their schools, yet He won every debate. The disciples were also looked down upon as “un-educated,” yet they “were with Jesus,” taught by Him, and knew the Scriptures better than the established leaders. Most Preterists I know are more educated in the Scriptures than those who have degrees from religious Futurist institutions. Are there any lessons here? What lessons can be drawn from the leaders’ refusal to acknowledge truth and perhaps from Futurist gatekeepers trying to demean Preterists?
10. Parable of the Two Sons – Narrative Connection: How does the Parable of the Two Sons (Matt. 21:28-32) directly flow from the confrontation in Matt. 21:23-27? In what ways does it build on the leaders’ refusal to acknowledge John’s divine authority, and how does it reinforce the article’s theme of doctrinal continuity between John and Jesus?
11. Repentance and Obedience in the Parable: In the Parable of the Two Sons, Jesus contrasts the repentance of sinners (tax collectors and prostitutes) with the hypocrisy of the religious leaders (Matt. 21:31-32). How does this parable illustrate the necessity of genuine repentance as taught by both John (Matt. 3:2) and Jesus (Matt. 4:17)? What does it reveal about the “way of righteousness” (Matt. 21:32) and its role in accessing the Kingdom?
12. Eschatological and Theological Implications of the Parable: The Parable of the Two Sons highlights the inclusion of the marginalized and the exclusion of unrepentant leaders, anticipating the AD 70 judgment and the transfer of the Kingdom (Matt. 21:43). How does this align with John’s and Jesus’ warnings of judgment (e.g., Matt. 3:7; 24:1-34), and what does it suggest about God’s redemptive plan for the repentant, including Gentiles, in the post-AD 70 era?