Messianic Prophecies from Zechariah

What do donkeys, silver, a struck shepherd, and crucifixion have in common? That’s right! They’re all associated with events during the last week of Jesus’ life. They’re related to Jesus’ triumphal entry, betrayal, arrest and abandonment, and crucifixion. But did you know these events were all messianic prophecies from Zechariah? Let’s look at how Jesus fulfills these very specific prophecies. We’ve pulled these short articles from the Jesus Bible. Keep reading to learn about these prophecies in their original historical context and how the NT writers apply them to Jesus.

Prophecy #1 – Lowly and Riding on a Donkey

Rejoice greatly, O daughter of Zion! Shout, O daughter of Jerusalem! Behold, your King is coming to you; he is just and having salvation, lowly and riding on a donkey, A colt, the foal of a donkey.”

Zechariah 9:9

Zechariah points toward a coming king. While the first part of this chapter concerns God’s judgment on Judah’s enemies, it goes on to declare that true peace ultimately comes through this coming King, the Messiah.

Zechariah announced his imminent arrival, admonishing Zion, or Jerusalem, to rejoice and shout. According to verse 9, this king proves to be righteous. Furthermore, his arrival brings salvation.

In a typical ancient Near Eastern context, a king’s arrival to a city would be marked by conspicuous pomp and pageantry. In this honor- and shame-based culture, anything less would be an affront to the king’s rule. Royalty traveled with an entourage. Here Zechariah’s royal prophecy pointed to the well-known ancient practice of kings who came in peace, riding into town on a donkey rather than a war horse.

Fulfillment

Entering the final week of Jesus’ earthly ministry, he asked his disciples to run an errand. If anyone asked the disciples what they sought, they were to respond that the Lord required it (Mt 21:2–3).

More than anyone else, Jesus knew who he was. He knew—in fact he inspired—the prophecy in Zechariah. So, in what many now call the Triumphal Entry, Jesus rode into Jerusalem on the back of a humble colt, the foal of a donkey; the symbol of a king arriving in peace. The whole city, Matthew records, wondered about the identity of this man (Mt 21:10). However, Jesus was not confused. As he rode in on the donkey, he claimed—in visible terms—to be the Messiah that this prophecy foretold.

Though Zechariah told them this was to come, the Jews failed to connect the prophetic dots. In tragic ways, they misunderstood Jesus. They celebrated him as a king on Sunday; they crucified him as a criminal the next Friday.

While the palm branches and shouting were appropriate, so was the donkey. This King ruled perfectly, including the attitudes with which he ruled. Deserving of all honor, he humbled himself, even to the point of death on a cross (Php 2:8). No one had ever seen a King like this. The next Sunday proved it.

Prophecy #2 – Thirty Pieces of Silver

Then I said to them, ‘If it is agreeable to you, give me my wages; and if not, refrain.’ So they weighed out for my wages thirty pieces of silver. And the Lord said to me, ‘Throw it to the potter’—that princely price they set on me. So I took the thirty pieces of silver and threw them into the house of the Lord for the potter.”

Zechariah 11:12–13

In these latter chapters, Judah’s situation escalated quickly. Zechariah got rid of three prominent shepherds, assuming their leadership role. However, he quickly tired of the people; they, in turn, detested him (v. 8). He, presumably to leave them to their sinful ways, promptly resigned from leadership (v. 9).

Zechariah’s severance package had not been made clear, so Zechariah gave them the option to pay him or not (v. 12). In a most inadequate middle ground, they sent him off for the price of a slave—thirty pieces of silver. He rejected this devaluation, hurling the coins to the potter at the house of the Lord as the Lord directed him (v. 13).

Fulfillment

The flock underestimated the worth of Zechariah’s leadership, assigning him a value the Lord found insufficient. However, this pales in comparison to the narrative in Matthew’s Gospel, which reports history’s worst appraisal of worth. God incarnate came to dwell with humanity. Humanity promptly sold him for thirty pieces of silver (Mt 27:1–10).

Prophecy #3 – Shepherd Struck, Sheep Scattered

Awake, O sword, against My Shepherd, against the Man who is My Companion,” says the Lord of hosts. “Strike the Shepherd, and the sheep will be scattered; then I will turn My hand against the little ones.”

Zechariah 13:7

Sheep are not the smartest creatures on the planet. In fact, their survival largely depends upon the care of their shepherd. In the final sections of Zechariah’s book, God described the leaders of Israel as cruel shepherds and the people as oppressed sheep.

Nevertheless, when a good shepherd finally began to care for the people of God, the sheep rejected him as well. Zechariah quoted these words: “Strike the shepherd, and the sheep will be scattered” (v. 7). God’s good shepherd would die, the flock would scatter and many would perish (v. 8). However, the Lord indicated that through that testing he would refine his remaining people (v. 9).

Fulfillment

Jesus quoted this prophecy on the evening of Judas’ betrayal. With the disciples gathered, he told them they would all scatter that night (Mt 26:31). And, just as Jesus foretold, the Gospels reveal that all the disciples soon fled (Mt 26:56).

Soon after, the Good Shepherd laid down his life for his wandering sheep (Jn 10:14–15). Though the shepherd would be struck, Jesus assured his disciples this would not be the end. He comforted them, saying, “After I have risen, I will go ahead of you into Galilee” (Mt 26:32). The rest of Matthew’s Gospel relates the fulfillment of this promise.

The balance of the New Testament details the full restoration of all of God’s people. Ultimately, Jesus’ death did not scatter his sheep. When the Good Shepherd was struck, God gathered them together (Jn 10:27).

Prophecy #4 – Seeing the One Whom They Have Pierced

And I will pour on the house of David and on the inhabitants of Jerusalem the Spirit of grace and supplication; then they will look on Me whom they pierced. Yes, they will mourn for Him as one mourns for his only son, and grieve for Him as one grieves for a firstborn.”

Zechariah 12:10

A number of centuries before Christ, the Word of God alluded to crucifixion as a form of execution—specifically, what would happen to the Messiah in his death. Immediately after sharing God’s promise to pour out a “spirit of grace” on his people, Zechariah mentioned the people looking upon “the one they have pierced” (Zec 12:10). Hundreds of years after the time Zechariah wrote, the Romans utilized crucifixion as a way to discourage subversive activity. In a crucifixion, authorities nailed the criminal to a cross where they often hung in agony for days until they died of multiple traumas (Ps 22:16).

The cross signified the deepest shame—the convicted criminal died, naked and suffering, in front of a public audience whose jeering or sheer horror at the sight only made it worse. Incredibly, almost impossibly, the One who spoke creation into existence submitted to this horrible form of death. On the cross, he sacrificed himself for the sins of all humanity; he hung on a cross between two criminals to forge a new pathway for people to find their way to God.

Fulfillment

On the day of Jesus’ execution, the Jewish leaders asked that his legs be broken so death would occur more quickly; they wanted the bodies down before the Sabbath. Pilate agreed. But after the soldiers broke the legs of the two rebels, they found Jesus already dead. Rather than breaking Jesus’ legs, one of the soldiers pierced Jesus’ side with a spear (Jn 19:33–34). John, knowing well the book of Zechariah, saw these events with his own eyes (Jn 19:35). In his Gospel, he made clear that nothing about Jesus’ crucifixion happened by chance. When he watched the spear pierce Jesus’ side, he remembered Zechariah’s prophecy. God continued to fulfill his Word, even in the death of God’s Son (Jn 19:37).

Of course, Jesus did not remain dead. John went on to tell God’s people much more about the Jesus who lived after the cross. When John described the return of this risen Christ, he used these words: “Look, he is coming with the clouds,” and “every eye will see him, even those who pierced him” (Rev 1:7). The pierced, crucified and risen Christ will return to rule over his people forever.

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