Introduction: A Messianic Spectacle

Having completed a five-part series demonstrating that, prior to Matthew 24-25, Jesus taught His second coming would occur within the lifetime and generation of the first-century church (cf. Matt. 10:22-23; 16:27-28; 23:39; 26:63-65; Luke 17:20-37), I believe it would be beneficial to undertake a series on Matthew 21-22. This series will show that the eschatology in these chapters also points to an AD 70 fulfillment. This approach will provide a comprehensive context before exegeting Matthew 24-25.

When Jesus rode into Jerusalem on a donkey (Matt. 21:1–11), He is bringing in the minds of His audience the fulfillment of Zechariah 9:9, Isaiah 62:11, and Psalm 118, enacting a prophetic drama that fulfilled Jewish Messianic hopes for a believing righteous remnant according to the Scriptures. Far from a military conqueror like Alexander the Great, a temporal king like Solomon, or a civic restorer like Nehemiah, Jesus entered as the humble King of Peace, inaugurating a spiritual New Covenant Kingdom. Matthew portrays Him as surpassing these Old Testament types, establishing an eternal Temple and peace through His suffering and judgment in AD 70. This entry marks the climax of Old Covenant history, culminating in the destruction of Jerusalem and the rise of Christ’s everlasting kingdom.

Isaiah 62:11

In Matthew 21:5, Jesus’ triumphal entry fulfills a conflation of Zechariah 9:9 (“Behold, your king is coming to you, humble, and mounted on a donkey”) and Isaiah 62:11 (“Say to the daughter of Zion, ‘Behold, your salvation comes’”).  Isaiah 62 is rich with eschatological imagery:

• Wedding motifs (vv. 4–5): God’s covenant love restores Israel, likened to a bride.
• New Jerusalem (v. 7): A restored city with open gates (v. 10) and a highway for the redeemed.
• Second exodus typology: Some interpret Isaiah 62 as foreshadowing the return from exile back into the land under Ezra and Nehemiah, which typifies the ultimate redemption and or “gathering” “in Christ,” the Messiah [not “in the land”].  “In the land” vs. “in Christ” is the covenantal shift between the old and new covenants.  Here Jesus is a greater Cyrus, Ezra, and Nehemiah that produces the true and everlasting restoration between man and God.  In Zechariah 9 Jesus is the greater Alexander.

Eschatological judgment and salvation:

Isaiah 62:11’s “reward” and “recompense” suggest Christ’s coming to save the remnant and judge the wicked, which you connect to both His first coming and the AD 70 destruction of Jerusalem as a second coming in judgment (cf. Matt. 16:27-28):

• “Behold, your salvation comes; behold, his reward is with him, and his recompense before him” (Isa. 62:11)
• “For the Son of Man is about to come with his angels in the glory of his Father, and then he will repay each person according to what he has done.  Truly, I say to you, there are some standing here who will not taste death until they see the Son of Man coming in his kingdom” (Matt. 16:27-28)

This context frames the triumphal entry (Matthew 21:1–11) and the temple cleansing (Matthew 21:12–17) as eschatologically charged events. Jesus’ actions signal not only His humble first coming but also the impending judgment on Jerusalem in AD 70, aligning with the Messiah coming to grant “salvation” and “recompense” of Isaiah 62:11. The next event of Jesus cleansing the temple, as a priestly act, could thus be seen as part of this judgment, inspecting and condemning the corrupt “house” (temple) in which if unclean, not one stone would be left upon another per Leviticus 14:33–53.

Zechariah 9: Historical and Prophetic Context

Zechariah 9:1–8 traces a military campaign from Damascus to Philistia, mirroring Alexander the Great’s conquest of the Levant (333–332 BC). Jerusalem is spared: “I will encamp at my house as a guard, so that none shall march to and fro” (Zech. 9:8). Josephus recounts Alexander’s peaceful entry into Jerusalem, guided by a dream and the High Priest’s presentation of Daniel’s prophecy, where he offered sacrifices in the Temple.[1] This historical type prefigures Jesus, the true King, who enters humbly to fulfill Zechariah 9:9: “Your king is coming to you, humble, and mounted on a donkey.”

Jesus as the Greater Alexander 

Alexander’s entry into Jerusalem, marked by military might yet divine restraint, foreshadows Jesus’ Triumphal Entry. Both are linked to Daniel’s prophecies: Alexander as the Greek king (Dan. 8, 11) and Jesus as the Son of Man (Dan. 7, 9). However, their aims differ. Alexander honored the Temple physically; Jesus cleansed it spiritually, declaring Himself the true Temple (John 2:19–21). Alexander’s empire crumbled; Jesus’ kingdom endures (Isa. 9:7). Some see the Parable of the Minas (Luke 19:11–27) as reinforcing this typology: like Alexander, Jesus departs to receive a kingdom, entrusts stewards, and returns to judge opponents, fulfilling the judgment on Jerusalem in AD 70 (Matt. 24:30–34).

Parallels Between Jesus and Alexander the Great

Parallels Between Jesus, Alexander, and the Parable of the Minas (Luke 19:11–27)

Jesus as the Greater Solomon

Solomon, the son of David, rode a mule at his coronation (1 Kings 1:33–38), symbolizing covenantal succession. Jesus, riding a pure donkey (Zech. 9:9), fulfills Genesis 49:10–11 and surpasses Solomon’s reign. Solomon’s 40-year rule brought political peace and a physical Temple (1 Kings 4:24–25; 6). Jesus, “greater than Solomon” (Matt. 12:42), offers spiritual peace, freeing souls from sin (Rom. 5:1), and builds a living Temple with Himself as the Cornerstone (1 Pet. 2:4–5). Like Solomon, Jesus reigned over Old Covenant Israel for approximately 40 years (AD 30–70, from His death and resurrection to the fall of Jerusalem), but His everlasting rule continues (Dan. 2:44; Heb. 1:8). While Solomon’s wisdom and wealth drew the Queen of Sheba (1 Kings 10:1–10), Jesus’ divine wisdom and universal kingship attract all nations (Matt. 2:1–12; 28:19).

Parallels and Typology Between Jesus and Solomon

Jesus as the Greater Nehemiah

My good friend Robert Cruickshank believes Zechariah 9:11-12 is referring to Israel coming back into the land under the restoration leadership of Ezra and Nehemiah.[2]  Per Robert’s view, I’m not sure how Zechariah 9 moves from the historical context of Alexander the Great’s conquests and his interaction with Jerusalem around 333–332 BC in verses 1–8 to the restoration themes tied to Ezra and Nehemiah’s time, roughly 458–424 BC, in verses 11–12.  But I’d love for you to check out my friend’s article for his perspective on Zechariah 9:11-12.  On the chance there is a connection here, we should note, theologians and commentators have long seen Nehemiah, the covenantal leader who rebuilt Jerusalem’s walls and restored its worship (Neh. 1–6, 13), as a type of Christ. James Hamilton nails this in his book Exalting Jesus in Ezra and Nehemiah (2014), showing how Nehemiah’s work points to Jesus’ Triumphal Entry (Matt. 21:1–11), where He rides in on a donkey to establish His New Covenant Kingdom.[3] Nehemiah’s humble service, despite opposition from Sanballat and Tobiah (Neh. 4:1–3), parallels Jesus’ entry on a donkey, symbolizing peaceful covenant restoration (Zech. 9:9). Nehemiah cleansed the Temple (Neh. 13:4–9); Jesus did so spiritually, declaring Himself the true Temple (Matt. 21:12–13). While Nehemiah rebuilt physical walls, Jesus builds the spiritual Jerusalem—the Church—as “living stones” (1 Pet. 2:4–5). The donkey, a “covenant donkey” tied to ratification ceremonies,[4] underscores Jesus’ role in ratifying the New Covenant through His blood (Matt. 26:28), surpassing Nehemiah’s temporal renewal.

Parallels and Typology Between Jesus and Nehemiah   

The Royal Donkey: A Theological Symbol 

Ken Way argues that Zechariah 9:9’s donkey is a “purebred son of a jenny,” not a youthful colt, emphasizing royal purity over Solomon’s mule, a hybrid symbolizing temporal rule.[5] Jesus’ donkey ride signals a humble, spiritual kingship, fulfilling the Davidic promise of an eternal kingdom (2 Sam. 7:12–13) and the “covenant donkey” tradition tied to covenant ratification (Gen. 49:11).[6] Unlike Solomon’s affluent coronation or Nehemiah’s civic restoration, Jesus’ entry prioritizes prophetic fulfillment, aligning with His mission to suffer and redeem (Isa. 53).

Psalm 118: Hosanna and the Cornerstone

The crowd’s cry of “Hosanna” (Matt. 21:9) echoes Psalm 118:25–26, a post-exilic hymn of covenant faithfulness. They hoped for a Temple-restoring Messiah to defeat Rome [possibly using the Temple as fortress as we see in the events of AD 67-70], but Jesus quotes Psalm 118:22–23: “The stone the builders rejected has become the cornerstone” (Matt. 21:42). He is the true Temple, rejected by Israel’s leaders but chosen by God. Those who stumble in unbelief face judgment, fulfilled in Jerusalem’s fall in AD 70 (Matt. 23:36–39).

Rabbinic Views: A Dual Messiah?

The Babylonian Talmud (Sanhedrin 98a) wrestles with how to reconcile two well-known Messianic texts and pictures:

Daniel 7:13: One like a Son of Man comes on clouds

Zechariah 9:9: The King comes humbly on a donkey

Some thought these texts could be reconciled as two different Messiah’s coming (Messiah ben Joseph and Messiah ben David) while others theorized:

“If Israel is worthy, He will come on the clouds; if not, humbly on a donkey.”

One Rabbi correctly understood this not describing two different Messiah’s or what kind of Messiahic arrival would take place in Israel if they were faithful or not, but rather:

“Messiah will be both powerfully exalted (‘clouds’) and humbly self-effacing (‘a  donkey’).”[7]

Jesus embodies this duality—entering humbly to suffer (Matt. 21:1–11) and returning in judgment (AD 70, Matt. 16:27-28; Matt. 24:27-30; 25:31). Unlike Alexander’s false divinity, Solomon’s flawed rule, or Nehemiah’s temporal reforms, Jesus is the true Son of God, fulfilling all roles perfectly (2 Cor. 1:20; Phil. 2:5–11).

Conclusion: The King of Peace and Judgment

Jesus’ Triumphal Entry was a prophetic act, surpassing the typologies of Alexander, Solomon, and Nehemiah. As a greater Alexander, He spared Jerusalem temporarily but judged it in AD 70, establishing a spiritual kingdom. As a greater Solomon, He brought eternal peace and built a living Temple. As a greater Nehemiah, He restored the true Jerusalem through His redemptive work. The generation that shouted “Hosanna” witnessed His return in salvation and judgment (Matt. 24:27-34; Luke 21:20-32), proving His kingship is not of this world (John 18:36) but reigns forever (Dan. 2:44) “within” the hearts of His people (Luke 17:20-37).

Study Questions:

1. Contextual Understanding: What is the main purpose of the article’s series on Matthew 21–22, and how does it relate to the author’s prior work or five part series on Matthew 10:17-23, 16:27-28; 23:39; 26:63-65; and Luke 17:20-37 as paving the contextual setting to understand Matthew 24–25?
2. Prophetic Fulfillment: How does Jesus’ triumphal entry in Matthew 21:1–11 fulfill the prophecies of Zechariah 9:9, Isaiah 62:11, and Psalm 118, according to the article?
3. Eschatological Significance: The article connects Jesus’ actions in Matthew 21 (triumphal entry and temple cleansing) to the AD 70 destruction of Jerusalem. How does it argue this connection reflects both salvation and judgment?
4. Typology of Alexander the Great: In what ways does the article compare and contrast Alexander the Great’s entry into Jerusalem (Zech. 9:1-8) with Jesus’ triumphal entry, and how does Jesus surpass Alexander as the “antitype”?
5. Parable of the Minas: How does the article use the Parable of the Minas (Luke 19:11–27) to reinforce the typology between Alexander the Great and Jesus, particularly in terms of judgment and kingdom establishment?
6. Typology of Solomon: The article describes Jesus as a “greater Solomon.”  In the Jewish mind would there be a connection between Solomon riding on a donkey and Jesus riding on a donkey?  What other specific parallels does it draw between Solomon’s reign and Jesus’ ministry, especially regarding peace, temple, and wisdom?
7. Typology of Nehemiah: How does the article, referencing Robert Cruickshank and James Hamilton, present Nehemiah as a type of Christ, and what are the key parallels between Nehemiah’s work and Jesus’ triumphal entry?
8. Theological Symbolism: According to the article, what is the significance of the “royal donkey” in Zechariah 9:9, and how does it reflect Jesus’ kingship compared to Solomon’s mule?  What kind of donkey did Jesus ride? 
9. Psalm 118 and Hosanna: How does the crowd’s cry of “Hosanna” in Matthew 21:9, linked to Psalm 118, reflect their expectations of the Messiah, and how does Jesus properly define these expectations?
10. Rabbinic Interpretations: The article mentions the Babylonian Talmud’s discussion of a dual Messiah or dual responses to Messiah (Daniel 7:13 vs. Zechariah 9:9). How does it explain Jesus fulfilling both the “clouds” and “donkey” prophecies?
11. New Covenant Kingdom: How does the article contrast the temporal achievements of Alexander, Solomon, and Nehemiah with Jesus’ establishment of an eternal, spiritual New Covenant Kingdom?
12. Critical Reflection: The article claims Jesus’ second coming occurred in AD 70. What evidence does it provide to support this view, and how might this interpretation challenge or align with traditional eschatological perspectives?

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[1] Josephus, Antiquities 11.8.5

[2] Robert E. Cruickshank, Jr., Double Restoration and Trouble with Equations:  Pop-Prophecy and Zechariah 9:11-12, 03/01/2025, https://burrosofberea.com/double-restoration-and-trouble-with-equations-pop-prophecy-and-zechariah-911-12/

[3] James M. Hamilton Jr., Exalting Jesus in Ezra and Nehemiah, Christ-Centered Exposition Commentary (Nashville: B&H Publishing Group, 2014), cited in Nick Batzig, “Nehemiah as a Type of Christ,” Feeding on Christ, September 8, 2014, https://feedingonchrist.org/nehemiah-type-christ/.

[4] Willem A. VanGemeren, ed., New International Dictionary of Old Testament Theology and Exegesis, vol. 1 (Grand Rapids: Zondervan, 1997), 575–577.

[5] Way, Kenneth C. “Donkey Domain: Zechariah 9:9 and Lexical Semantics.” Journal of Biblical Literature 129, no. 1 (Spring 2010): 105–114. Way examines four Biblical terms, three found in Zechariah 9:9—ḥamor, ’ayir, ’aton—and a fourth pērēd in Zechariah 14:15. […] Way believes ben ’atonot is not meant to describe a foal, but rather indicates the animal is a purebred jenny. Then Zechariah 9:9 would describe a single donkey (ḥamor), not any donkey, specifically a jackass (’ayir), and not any jackass, specifically a ben ’atonot, that is, a purebred jackass.

[6] Ibid., Willem A. VanGemeren,

[7] Michael L. Brown, Answering Jewish Objections to Jesus: Messianic Prophecy Objections, Vol. 3 (Grand Rapids: Baker Books, 2003), 73. Brown cites Jewish traditions that acknowledge both Zechariah 9:9 and Daniel 7:13 refer to the same Messiah, depending on Israel’s worthiness—yet some rabbis proposed that both modes would be fulfilled in a single person.