Matthew 21: Triumphal Entry and Change of Tenants

Matthew 21: Triumphal Entry and Change of Tenants

Collin Leong. May 15, 2025

(v1-11)  Jesus Triumphal Entry  (Zechariah 9:9-13; Mark 11:1-11; Luke 19:28-40; John 12:12-19)

(v1-7) They came to Bethphage on the Mount of Olives, near to Jerusalem. Jesus sent two disciples to the village nearby and they will see a donkey tied there, with the colt beside her. They are to untie them and bring it to Him. If anyone says anything to them, tell them that the Lord needs them, and he will send them right away. The disciples went and did what Jesus told them. They brought the donkey and the colt and placed their cloaks on them for Jesus to sit on. 

Jesus came to Jerusalem five days before the Passover. Before this He was at Bethany, being anointed by Mary with perfume at Lazarus house (John 12:1-3). The day He entered Jerusalem is celebrated as Palm Sunday by Christians, the day of the final week leading to His crucifixion. 

 

This fulfilled the prophecy of Zechariah 9:9 - "Rejoice greatly, Daughter Zion! Shout, Daughter Jerusalem! See, your king comes to you, righteous and victorious, lowly and riding on a donkey, on a colt, the foal of a donkey."

Zechariah did not say this just because of Jesus' humility. A donkey is the only animal that has a "cross" on it's body. There's a dark stripe from mane to tail, and a crossing stripe across the shoulder. The cross is especially visible on gray or light-colored donkey. It's no coincidence that Jesus came into Jerusalem on a cross and left Jerusalem with a cross. 

Note that Matthew wrote that there 2 donkeys - one is the mother, and one is the colt. Mark 11:2 and Luke 19:30 only mentioned the colt, focusing on the animal Jesus rode on. Zechariah's prophecy also mentioned a donkey, and a colt. It makes sense that the mother came along with the colt, as the colt had never been ridden before, having its mother nearby could have helped keep it calm during the journey. However, Jesus could have included the mother to complete the prophecy. 

(v8-11) A very large crowd spread their cloaks and branches and spread them on the road as Jesus came into Jerusalem. Some of the crowds that went ahead of Him shouted: 

“Hosanna to the Son of David!”

“Blessed is he who comes in the name of the Lord!” 

“Hosanna in the highest heaven!”

The whole city was stirred and asked who is He. The crowds answered, “This is Jesus, the prophet from Nazareth in Galilee.”

The word "Hosanna" comes from the Hebrew phrase "Hoshiana", which means "Save us!" or "Save now!"  It is the same words used in Psalms 118:25 that says "Lord, save us! Lord, grant us success!"  By the time of Jesus, it had evolved into an expression of praise and recognition of the Messiah.

Psalm 118 was part of the Hallel Psalms (Psalms 113–118), traditionally sung during Jewish festivals like Passover. When the crowds shouted "Hosanna!" in Matthew 21:9, they were likely referencing this psalm. This connection highlights the prophetic fulfillment of Psalm 118 in Jesus' triumphal entry into Jerusalem.

However, the crowd told the others that Jesus is a prophet from Nazareth, rather than the Messiah from Heaven. While some recognized Him as the Messianic King, others were still uncertain. The Jewish expectation of the Messiah was often tied to a political deliverer who would free them from Roman rule. Since Jesus did not fit that expectation, many viewed Him as a prophet rather than the promised Savior.

Isn't it sad that the crowd shout praises to Jesus now, but later they shout angrily to crucify Him.

(v12-13) Jesus Drove Out Merchants from the Temple (Mark 11:15-19; Luke 19:45-48; John 2:12-25)

(v12-13) Jesus entered the temple courts and drove out all who were buying and selling. He overturned the tables of the money changes and the benches of those selling doves. He said that is is written that "my house will be called a house of prayer", but you are making it 'a den of robbers.'

The temple was used for sacrifice. It's the place of joy and praise. God is there, and we are worshipping Him. However at that time, the people and priests were focusing on money. The temple generates income by taxes and selling temple currency. They also profit from selling animals for sacrifice. Even pharisees can be bribe to be the high priests. His house is a place of prayer, not just for the Jews but for all nations. 

(v14-17)  Jesus Healed at the Temple

(14-15) The blind and the lame came to Jesus at the temple and He healed them. But the chief priests and teachers of the law saw the wonderful things he did, and the children shouting in the temple courts "Hossana to the Son of David," they were indignant. 

As I said just now, that phrase is to welcome the Messiah. No wonder the priest we upset as they do not accept Jesus as the Messiah. 

(16-17) They asked Jesus if He hears what these children are saying. Jesus said yes, he did. Then he quoted the verse: "‘From the lips of children and infants you, Lord, have called forth your praise’  (Psalm 8:2 Septuagint). Then He left them and went to Bethany, where he spent the night. 

(v18-22) Jesus Curses a Fig Tree (Mark 11:12-14; Mark 11:20-26)

(18-20) When Jesus was on his way back to Jerusalem in early morning, he was hungry. He went up to the fig tree by the road but found no fruits. He cursed the tree that it will never bear fruit again. Immediately, the tree withered. The disciples were amazed that the fig tree withered so quickly. 

(21-22) Jesus told them that if they have faith and do not doubt, not only you can do what was done to the fig tree, but they can ask this mountain to throw itself into the sea, and it will be done. If they believe, they will receive whatever they ask for in prayer.

The physical mountain Jesus is referring to could be the Mount of Olives. However, "mountains" also symbolizes obstacles or challenges that can be overcome through faith. We have to ask God in prayer without doubt, and expect that we will receive it, sooner or later. (This presumes your request is for the good of yourself and/or other people.)

(v23-27) The Authority Of Jesus Questioned (Mark 11:27-33; Luke 20:1-8)

(v23-25)  Jesus was teaching in the temple courts. The chief priest and elders came and asked Him who gave Him authority to do these things. Jesus told them if they can answer His question, then He will tell them who is His authority. The question is whether John's baptism comes from heaven or from human origin. 

(v26-27) They discussed among themselves and realized that if they say it is from heaven, then Jesus will ask them why didn't you believe him? And if they say its from human origin, then they are afraid of the people who believe that John was a prophet. So they told Jesus that they don't know the answer.  Jesus said: “Neither will I tell you by what authority I am doing these things."

The leaders a probably thinking John's baptism is from human origin, since they have never listened to him before. However they are fearful of the people rather than to tell the truth. Since they can't answer, Jesus also refused to answer their questions. 

The bible has told us this authority is from God the Father. Matthew 28:18 – "All authority in heaven and on earth has been given to me." Also  Philippians 2:9-10 – "Therefore God exalted him to the highest place and gave him the name that is above every name, that at the name of Jesus every knee should bow."   

(28-32) Parable of the Two Sons

(28-30)  Jesus told a parable about a man with two sons. The man went to this first son and asked him to work in the vineyard. This son told him he won't do it. However, later on he changed his mind and went. The man also went to the second son and told him the same thing. The second son said he will go, but ended up not going. 

(v31-32) Jesus ask the priests and elders which on the son did what his father wanted? They replied and said the first one. 

Jesus said that the tax collectors and prostitutes will enter heaven ahead of them. For John showed 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. 

Jesus is equating the religious leaders to the second son. While they appear to be righteous and obedient to the law, but inwardly they did not do what the Father wants. The sinners, like the first son, at first live for themselves, but later changed their minds when they heard John's teaching and repented and became believers. But even then, the religious leader still refuse to repent and still refuse to believe in John and Jesus.

(33-46) Parable of the Tenants (Mark 12:1-12; Luke 20:9-18)

(33-34) Jesus told them another parable. A landowner planted a vineyard and put a wall around it, dug a winepress in it and built a watchtower.  Then he rented the vineyard to some farmers and he moved to another place. When the harvest time approaches, he sent his servants to the tenants to collect his fruit. 

When I read the above, I was wondering why did Jesus mentioned the wall, winepress, and watchtower. The parable will work perfectly fine without these details. If we look deeper, we realize that the:

• The vineyard represent Jerusalem; however, Jerusalem also represent Israel. For example, in the news, we often here that "Washington has decided" or "According to Beijing", meaning that the capital city represent the whole nation. 
• The wall God puts around Jerusalem symbolize his protection and care for His people. They were set apart for His purposes. 
• The Winepress is used to extract juice from grapes. It represents the expectation that God's people would bear the fruits of righteousness. (In certain scripture, it also symbolizes judgment.)
• The Watchtower serves as a place of oversight. This represent God's watchful care over His people. 
• The tenants are those that God appointed to take care of the vineyard, so that they can guide the people to produce much fruit. 

This means that God truly loved the people of Israel, and He truly loves us as well. That's why He needed good "tenants" to take care of the vineyards, or be shepherds of His sheep. 

(35-39)  However, the tenants have different ideas. They keep beating and killing the servants sent to them every time they were sent. Finally the landowner sent his son, believing that they will respect him. However, the tenant said to themselves that if they kill the heir, they can take his inheritance. They took the son and threw him out of the vineyard can killed him. 

The word "servants" represents the Old Testament prophets, including John the Baptist. Many of the prophets sent to Israel are rejected, tortured and killed. (See appendix for examples.)  Jesus' Himself said: "Jerusalem, Jerusalem, who kills the prophets and stones those sent to her!" (Matthew 23:37). Again, this refers to Israel. 

The "son" represents Jesus Himself. They not only rejected Jesus, they also tortured and killed Him. Interestingly, Jesus said that they "threw him out of the vineyard and killed him."  Indeed, Jesus was killed at Golgotha, outside of the city of Jerusalem. 

(40-44) Jesus asked them that, when the landowner returns, what will he do to those tenants? They answered that he will bring the "wretches" to a "wretched end", and he will rent the vineyard to other tenants, who will give him his share of the crop at harvest time. 

Jesus asked them if they have read in the scripture: "‘The stone the builders rejected 

has become the cornerstone; the Lord has done this, and it is marvelous in our eyes’ "?  (Psalm 118:22,23)

Jesus then said that the Kingdom of God will be be taken away from them and given to a people who will produce its fruit. Anyone who falls on this stone will be broken to pieces, anyone on whom it falls will be crushed. (v44)

In Psalm 118:22-23, Jesus is the rejected stone—the Messiah whom the religious leaders refused to accept. The cornerstone ensures the building is properly oriented and provides a reference point for all other stones. In ancient architecture, careful measurements were taken to ensure it was square, guiding the rest of the construction. Despite their rejection, He becomes the cornerstone, the foundation of God's kingdom.

In v44, the one who "falls on this stone and broken to pieces" are often interpreted as brokenness, conviction, repentance, or personal transformation. These are for those who eventually believe in Jesus. Those on whom the stone falls (symbolizing final judgment) will face destruction. This interpretation has basis using Isaiah 8:14-15, where God is described as a stone that causes people to stumble, and Daniel 2:34-35, where a divine stone crushes earthly kingdoms.

The religious leaders agree that the tenant should be judged and come to an end; They also agree that the vineyard should be given to new tenants. Jesus expanded what they say to include the "Kingdom of God", that includes all nations of the earth. If they are not able to produce fruit in a small state of Israel, and in fact were hostile to the Son, then they cannot be asked to provide for spiritual needs of the earth. 

This "new tenant" who will "produce fruit" are the New Testament people, including the gentiles. Starting with His Jewish disciples, they will expand the Gospels to surrounding nations and then around the world and guide them through the churches on the right way to worship God. 

(v45-46)  The priests and the Pharisees realized that Jesus was talking about them. They looked for a way to arrest Him, but they were afraid of the crowd because the people held that he was a prophet. 

Appendix

1. Example of prophets being tortured or killed:

• Zechariah, son of Jehoiada: He was stoned to death by order of King Joash after rebuking the people for their disobedience to God (2 Chronicles 24:20-22)

• Uriah, son of Shemaiah: He prophesied against Jerusalem and Judah but was pursued by King Jehoiakim, captured in Egypt, and executed (Jeremiah 26:20-23)

• Isaiah: His messages were often ignored, and tradition holds that he was sawn in half.

• Elijah: He fled for his life after Queen Jezebel sought to kill him.

• John the Baptist: He was beheaded by Herod Antipas.

2. The temple during Jesus' time collected taxes from worshippers. The most well-known tax was the Temple Tax, which was a mandatory annual payment for Jewish men. Here’s how it worked:

1. The Temple Tax

• Based on Exodus 30:13-16, every Jewish male over 20 years old was required to pay half a shekel annually for the upkeep of the temple.
• This tax was still collected in Jesus’ time (see Matthew 17:24-27, where Jesus instructs Peter to find a coin in a fish’s mouth to pay the tax).
• The money changers in the temple likely helped convert foreign currency into the required Tyrian shekel, which had high silver content and was accepted for temple use.

2. Other Temple Payments

• Worshippers also bought sacrificial animals (like doves, lambs, and oxen) for offerings, which could be costly.
• There were also freewill offerings and vows that people would donate to the temple treasury.

While paying the temple tax was a normal practice, Jesus criticized the corruption associated with money changing and selling sacrifices (Matthew 21:12-13). He opposed the exploitation of worshippers rather than the temple tax itself.