Commentary on Matthew 21:23-32

Matthew 21 contains a unique parable that has no Synoptic parallels. The Parable of the Two Sons (21:28–32) is inserted between the passage questioning Jesus’s authority (21:23–27) and the Parable of the Wicked Tenants (21:33–46), which are contiguous in Mark 11:27–12:12. Exploring how this Matthean material is integrated into the Markan framework, therefore, provides a useful point of entry for exegesis.

At first glance, the parable appears simple: The first son initially refuses his father’s command to work in the vineyard but later obeys, whereas the second promptly agrees, yet fails to act. Thus, when Jesus asks, “Which of the two did the will of the father?” the answer is obvious: “The first” (21:31).

The difficulty, however, emerges in Jesus’s subsequent contrast between his immediate hearers (“you”) and “the tax collectors and the prostitutes” (21:31–32). Which group corresponds to which son? This ambiguity may explain why some ancient manuscripts reverse the sons’ order to create smoother parallels.¹ Yet the passage need not be interpreted through the broader biblical motif of the younger son displacing the elder. Instead, both sons function as contrasting responses directed toward a single audience—the “chief priests and the elders of the people” (21:23), whom Jesus addresses as “you” (hymeis).

Immediately before the parable, these authorities confront Jesus in the temple, demanding to know “by what authority” he is “doing these things” (21:23–24). Their challenge and Jesus’s rhetorical counterquestion carry into the following exchange, introduced by Jesus’s question, “What do you think?” (21:28). The parable, therefore, confronts the religious leaders with whether they are truly doing the will of the Father. Through Matthew’s redaction, this question extends into the Parable of the Wicked Tenants, reinforcing the chapter’s overarching concern with authority and leadership.

Where were these high authorities of Israel when Matthew’s Gospel was written? Matthew’s historical audience lived in the aftermath of the Jewish War. They knew that the Jerusalem Temple had been destroyed and the priesthood dismantled. Amid this absence of strong leadership, Jesus’s words to the chief priests and elders would have poignantly reminded Matthew’s audience of how these leaders had recently failed their people. They were the second son in the parable. They could have become the first son, but they never chose that path.

In particular, Matthew’s historical and literary context highlights three areas of leadership failure. The first is material. The leaders’ refusal to work in the vineyard signifies their refusal to bear fruit and thus their failure to feed the hungry. They neglected the poor struggling to survive under Rome’s heavy taxation, and the war only worsened the situation (see also Matthew 17:24–27).² This material dimension appears elsewhere in chapter 21: Jesus curses the fruitless fig tree (21:18–19), and the Parable of the Wicked Tenants in the Vineyard likewise points to the leaders’ unjustifiable failure to produce the fruits of God’s kingdom (21:41, 43) both materially and spiritually.

The second failure stems from entitled elitism. By Matthew 21:23–27, the leaders already knew of Jesus’s cleansing of the temple, where he overturned the money changers’ tables and performed healings (21:12–17). Yet instead of believing in him, they question his authority, treating him as someone lacking their religious and social pedigree. They deliberately refuse to acknowledge the heavenly origin of John’s baptism (21:25, 32; see also 17:12) and fail to accept Jesus as God’s Son who came to serve his people. To them, the popularity and authority of John the Baptist and Jesus appear only as threats to their own status and prestige.

Although the chief priests were appointed by God and the elders were elected by God’s people, they professed allegiance to God in empty words alone while failing to fulfill their divine calling to serve others (20:25–27). Like the second son—whose reply, “Yes, Master” (egō, kyrie), sounds emphatically obedient—their words never translated into action.

Ultimately, these leaders’ failures are rooted in a profound spiritual deficiency. John the Baptist came proclaiming the way of righteousness through the baptism of repentance (3:1–12),³ yet they did not change their minds, thereby rejecting Jesus as the Messiah (21:39, 42). In stark contrast stand the tax collectors and prostitutes, who, though regarded among the most despised and dishonorable in society, believe John, repent, and thus enter God’s kingdom ahead of them. Like the wicked tenants in the following vineyard parable, these authorities are destined to face judgment and “a miserable death” (21:41, 43–44).

For Matthew, this failure of Israel’s leaders was catastrophic, as it ultimately led to “the tragic events of 70 CE” (22:1–14; 23:3–36; 27:25).⁴ Reflecting on the recent past, Matthew now notes that when “the chief priests and the Pharisees heard [Jesus’s] parables, they realized that he was speaking about them” (21:45, emphasis added; see also Mark 12:12; Luke 20:19). Thus, Matthew’s critique does not merely apply to past authorities. Matthew’s community now appeals to its contemporaneous Pharisaic groups, from whom the original Mattheans were separated: As new community builders in the postwar setting, the Pharisees rejected the Lord’s cornerstone (21:42), but it is not too late to change their minds (metamelomai), like the first son.

The English translation of the Greek metamelomai does not fully capture its nuance, for metamelomai doesn’t simply mean “on second thought.” It connotes repentance and regret, from which acts of justice and humble service flow. Without repentance, the authority of religious and social leaders is rendered illegitimate. In a wartorn Jewish society marked by vivid memories of leadership failure, Matthew emphasizes the grave responsibility of community leaders: They are urged to undertake the life-giving work of caring for the vulnerable and downtrodden whom God has entrusted to them.

Notes

1. For example, Θ, f ¹³, 700, a majority of Bohairic Coptic manuscripts. See Pierre De Martin De Viviés, “Les deux fils envoyés à la vigne (Mt 21,28-32): Une parabole dans tous ses états,” Revue théologique de Louvain 46 (2015): 84–96.
2. Eunyung Lim, “Entering the Kingdom of Heaven Not Like the Sons of Earthly Kings (Matt 17:24–18:5),” Catholic Biblical Quarterly 83.3 (2021): 425–445.
3. “Righteousness” (or “justice”; Greek, dikaiosynē; Hebrew, tzedakah), which Matthew frequently uses, is a Jewish concept connoting “giving generously to the poor or almsgiving (Deut 14.22; 16.20), and by extension any loving act” (cf. b. B. Bat. 9b; b. Sukk. 49a). Aaron M. Gale, “The Gospel According to Matthew,” in The Jewish Annotated New Testament, ed. Amy-Jill Levine and Marc Zvi Brettler, 2nd ed. (New York: Oxford University Press, 2017), 15.
4. Gale, “The Gospel According to Matthew,” 10.