Matthew Chapter 21

What is the meaning of Matthew 21?

Have you ever witnessed someone walk into a room and completely upend the established order? That moment when everyone realizes the rules of the game have suddenly changed? Matthew 21 captures Jesus doing exactly this—bursting into Jerusalem not as a humble carpenter from Nazareth, but as a king claiming His rightful throne.

The streets of Jerusalem are electrified with expectation as Jesus orchestrates a royal entrance that deliberately fulfills ancient prophecies. Palm branches wave, cloaks carpet the road, and “Hosanna!” echoes through the air. But this king doesn’t head for a palace—instead, He marches straight into His Father’s House, the Temple and starts flipping tables, driving out merchants, and healing the broken. The religious power brokers are furious: “Who does this man think He is?”

What follows is a series of confrontations and parables that cut to the heart of spiritual authority. Jesus withers a fruitless fig tree with just His words, silences the elite religious scholars with questions they dare not answer, and tells stories that barely disguise His accusation: “You’ve had your chance to tend God’s vineyard, and you’ve failed.” Like a chess grandmaster making His final moves, Jesus deliberately pushes the authorities toward a decision they’ve already made in their hearts. This explosive chapter reveals what happens when God’s kingdom crashes into our carefully ordered religious systems—and why it still challenges us to choose which king we’ll truly serve today.

Context of Matthew 21

Within the Gospel of Matthew, chapter 21 serves as a crucial turning point, marking the beginning of Yeshua’s final week before His crucifixion. This chapter follows His ministry in Galilee and trans-Jordan regions and precedes His extended teachings about the end times and His approaching sacrifice. The events recorded here fulfill numerous prophecies and demonstrate Yeshua’s identity as the promised Messiah of Israel.

In the broader biblical narrative, this chapter echoes significant themes from the Hebrew Scriptures (Old Testament). The triumphal entry recalls Zechariah 9:9, where the prophet foretold the coming of the King on a donkey. The Temple cleansing connects to Malachi 3:1-3, which prophesied the Lord’s sudden coming to His Temple. These events demonstrate how Yeshua’s actions deliberately fulfilled and embodied prophetic expectations about the Messiah.

Ancient Key Word Study

• Hosanna (ὡσαννά / הושע נא) – This Hebrew-origin word literally means “save now” or “save, we pray.” In first-century usage, it had evolved into both a cry for salvation and an expression of praise. Its use during the triumphal entry connects to Psalm 118:25-26, a messianic psalm traditionally recited during Passover.
• Authority (ἐξουσία) – Used multiple times in this chapter, this Greek term denotes both the right and the power to act. It carries legal, moral, and spiritual implications, representing not just ability but legitimate right to exercise power.
• Stone (λίθος) – In quoting Psalm 118:22, this word carries deep messianic significance. The rejected stone becoming the cornerstone was a powerful metaphor in ancient construction, representing something deemed worthless becoming essential.
• Kingdom (βασιλεία) – This term appears in the context of the kingdom being taken away from the current leaders. In Jewish thought, it represented not just political rule but God’s sovereign reign and the manifestation of His will on earth.
• Fig Tree (συκῆ) – Beyond its literal meaning, the fig tree served as a prophetic symbol of Israel in the Hebrew Scriptures. Its appearance here carries significant theological weight regarding spiritual fruitfulness and judgment.
• Temple (ἱερόν) – This term specifically refers to the entire Temple complex, not just the sanctuary building. It represented the center of Jewish religious life and the meeting place between God and His people.
• Mountain (ὄρος) – Used in Yeshua’s teaching about faith, this word symbolized immovable obstacles. In Jewish literature, “mountain” was often used metaphorically for great difficulties or challenges.

Matthew 21 Unique Insights

The triumphal entry occurred on the 10th of Nisan, the very day when Jewish families were selecting their Passover lambs according to Exodus 12:3. As Yeshua entered Jerusalem, He was presenting Himself as the ultimate Passover Lamb, precisely on schedule with the divine calendar. This timing would not have been lost on Matthew’s Jewish audience.

The cursing of the fig tree presents an enacted parable that many scholars connect to Micah’s lament in Micah 7:1-6. According to the Talmud (Sukk. 28b), the fig tree was associated with Torah study because, like the fig, the more one studies Torah, the more “flavor” one finds. Yeshua’s action, therefore, symbolized judgment not just on fruitlessness but on a system that had preserved the outward form of religion while missing its heart.

The Targum on Psalm 118 (quoted in v. 42) explicitly connects the “stone which the builders rejected” with King David and ultimately the Messiah. Early rabbinic literature (Genesis Rabbah 71:9) includes a tradition about a stone rejected during the Temple construction that eventually became the cornerstone, providing a rich background for Yeshua’s application of this psalm to Himself.

The children’s praise in the Temple (v. 15-16) connects to Psalm 8:2, where the Hebrew word for “strength” (עז) can also mean “praise.” This wordplay suggests that the praise of children establishes a stronghold against God’s enemies, explaining why their recognition of Yeshua was particularly significant.

Question the Text

• Verse 1: Why did Jesus specifically send two disciples rather than one or more? Is there symbolic significance to this number in the context of Jewish tradition or Jesus’ ministry?
• Verse 2-3: How did Jesus know exactly where the donkey and colt would be? Does this demonstrate His divine foreknowledge, or had He made prior arrangements? And why does He use the phrase “The Lord needs them” as the only explanation?
• Verse 5: Why does Matthew quote from both Isaiah 62:11 and Zechariah 9:9 but attribute it as if it were a single prophecy? What theological point is he making by combining these texts?
• Verse 7: How could Jesus physically ride on garments placed on both a donkey and a colt simultaneously? Is Matthew suggesting Jesus rode both animals at different times, or is there a translation issue at play?
• Verse 9: Why do the crowds use the term “Son of David” rather than other messianic titles? What specific expectations might this reveal about their understanding of who Jesus was?
• Verse 10-11: Why does the crowd identify Jesus merely as “the prophet from Nazareth” after just hailing Him as the “Son of David”? Does this suggest confusion about His identity, or different groups having different understandings?
• Verse 12: What gives Jesus the authority to drive out the money changers? Would this not have required permission from the temple authorities, and why didn’t the temple guards intervene?
• Verse 14-15: Why were the chief priests and teachers of the law indignant about children shouting “Hosanna to the Son of David” rather than about the healings themselves? What reveals more about their hearts – their response to miraculous healing or their response to worship?
• Verse 16: Why does Jesus quote from Psalm 8:2 where יהוה (Yahweh) is addressed, applying it to Himself? Is He deliberately making a claim to divinity?
• Verse 19: Why would Jesus curse a fig tree for not having fruit when, as Mark notes, it wasn’t even the season for figs? Is this an act of frustration or is the fig tree serving as a symbolic lesson about Israel?
• Verse 21-22: Does Jesus’ promise about faith moving mountains apply literally to any prayer request, or are there implied limitations? How do we reconcile this with prayers that seem to go unanswered?
• Verse 23: Why do the religious leaders question Jesus’ authority now, after He had been teaching and performing miracles for years? What about the temple cleansing particularly threatened them?
• Verse 25: Why does Jesus answer their question with another question rather than directly asserting His divine authority? What does this reveal about His approach to confrontation?
• Verse 31-32: How could tax collectors and prostitutes be entering the kingdom of God ahead of religious leaders? Doesn’t this invert the expected religious hierarchy of the time? What does this suggest about the nature of true repentance?
• Verse 43: When Jesus says the kingdom will be taken away and given to a people who will produce its fruit, is He predicting the inclusion of Gentiles, or referring to a faithful remnant within Israel? How would first-century hearers have understood this threatening statement?
• Verse 46: Why didn’t the religious leaders arrest Jesus immediately if they wanted to seize Him? What does this reveal about the power dynamics between religious authorities, the Roman government, and public opinion in Jerusalem during this period?

Matthew 21 Connections to Yeshua

This chapter powerfully demonstrates Yeshua’s identity as the promised Messiah through multiple prophetic fulfillments. His orchestrated entrance into Jerusalem on a donkey deliberately enacted Zechariah’s prophecy, while His Temple cleansing fulfilled Malachi’s prediction of the Lord’s sudden appearance in His Temple. These actions weren’t merely coincidental fulfillments but calculated demonstrations of His messianic identity.

The parables in this chapter reveal Yeshua’s unique authority as both Judge and Cornerstone of God’s kingdom. The vineyard parable particularly foreshadows His rejection and crucifixion while prophesying the extension of God’s kingdom beyond Israel to include the Gentiles. His teaching about faith and prayer (v. 21-22) establishes Him as the mediator of a new covenant relationship with God, where authority is granted to believers through faith in Him.

Matthew 21 Scriptural Echoes

The chapter resonates deeply with numerous Old Testament passages:

• The triumphal entry fulfills Zechariah 9:9 and echoes Solomon’s coronation in 1 Kings 1:33.
• The Temple cleansing recalls Malachi 3:1-3 and Zechariah 14:21.
• The cursed fig tree imagery parallels Hosea 9:10 and Jeremiah 8:13.
• The vineyard parable draws from Isaiah 5:1-7 and Psalm 80:8-16.
• The cornerstone reference comes from Psalm 118:22-23.

Matthew 21 Devotional

This chapter challenges us to examine our response to Yeshua’s authority in our lives. Like the fig tree, we’re called to bear authentic spiritual fruit, not just maintain religious appearances. The power of faith described in verses 21-22 isn’t about manipulating God through prayer but about aligning our hearts with His purposes through genuine trust and submission.

The parables remind us that God looks at our actions more than our words. Like the first son who initially refused but later obeyed, we’re called to authentic repentance and obedience, not just verbal assent. The rejection of the cornerstone warns us against missing God’s work because it doesn’t match our expectations.

Did You Know

• The cry “Hosanna to the Son of David” was traditionally associated with the Feast of Tabernacles, making its use at Passover particularly significant as a messianic declaration.
• The money changers in the Temple operated under the authority of the priestly family of Annas, explaining why the religious leaders were particularly angered by Yeshua’s actions.
• The withered fig tree incident is the only destructive miracle recorded in the Gospels, highlighting its importance as a prophetic sign.
• The cave where the money changers operated was called the “Cave of Stores” and was part of the Royal Stoa complex built by Herod the Great.
• The “chief priests and elders” mentioned were likely members of the Sanhedrin, Judaism’s supreme court, making their confrontation with Yeshua an official inquiry.
• The vineyard parable draws on a rich tradition of vineyard imagery in Jewish literature, where Israel was often compared to a vineyard (Isaiah 5).
• The phrase “Son of David” appears in Matthew more than any other Gospel, emphasizing Yeshua’s royal messianic claims.
• The Temple markets were known as the “Bazaars of the Sons of Annas,” notorious for their corrupt practices in selling sacrificial animals.
• The children’s praise in the Temple likely included pilgrim children who had come for Passover, making it a powerful testimony from “outsiders.”
• Archaeological evidence has confirmed the extensive commercial activity in the Temple courts during the first century.