Matthew Chapter 21

The Beginning of Jesus’ Last Week
A. The Triumphal Entry

1. Matthew 21:1–6 – Jesus Instructs His Disciples Regarding Preparation for His Triumphal Entry into Jerusalem

“Now when they drew near Jerusalem, and came to Bethphage, at the Mount of Olives, then Jesus sent two disciples, saying to them, ‘Go into the village opposite you, and immediately you will find a donkey tied, and a colt with her. Loose them and bring them to Me. And if anyone says anything to you, you shall say, “The Lord has need of them,” and immediately he will send them.’ All this was done that it might be fulfilled which was spoken by the prophet, saying: ‘Tell the daughter of Zion, “Behold, your King is coming to you, Lowly, and sitting on a donkey, A colt, the foal of a donkey.”’ So the disciples went and did as Jesus commanded them.” (Matthew 21:1–6, NKJV)

a. “When they drew near Jerusalem” – Jesus approached the city of destiny. Knowing full well what awaited Him—betrayal, condemnation, crucifixion (Matthew 20:18–19)—He willingly moved toward Jerusalem. This demonstrated divine courage and sovereign control. Unlike previous times when Jesus avoided public recognition (Matthew 8:4; Matthew 12:16), here He orchestrated a public display in direct fulfillment of prophecy, openly presenting Himself as the Messiah.

b. “Bethphage, at the Mount of Olives” – Bethphage was a small village east of Jerusalem, adjacent to Bethany, situated on the Mount of Olives. This mountain, standing opposite the Temple Mount, held prophetic significance (Zechariah 14:4) and provided a majestic entry point into Jerusalem. Jesus chose this route not randomly but in line with Zechariah’s prophetic vision of the coming King.

c. “You will find a donkey tied, and a colt with her” – Jesus gave detailed prophetic knowledge to His disciples. He foresaw the exact location and condition of the animals. The colt, which had never been ridden (Mark 11:2; Luke 19:30), would demonstrate Christ’s divine authority over creation—He could sit upon it without resistance or fear from the unbroken animal. The presence of the mother donkey helped calm the colt amid the chaos of a crowded procession.

d. “Loose them and bring them to Me” – The authority Jesus claimed here is significant. He identified Himself not just as a rabbi or prophet but as “the Lord.” In a culture where ownership and livestock were precious commodities, to say, “The Lord has need of them,” implied that Jesus had sovereign right over all possessions. Spurgeon comments, “What a singular conjunction of words is here—‘the Lord’ and ‘hath need’! Jesus, without laying aside His sovereignty, had taken a nature full of needs.”

e. “That it might be fulfilled which was spoken by the prophet” – This fulfillment comes from Zechariah 9:9, a clear Messianic prophecy. The quoted passage says:

“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, NKJV)

Matthew slightly condenses and adapts the quotation to highlight Jesus' humility and peaceful arrival. The King enters not as a military conqueror, but as the Prince of Peace—lowly, accessible, and gentle (cf. Isaiah 9:6; Luke 2:14). In contrast to Roman generals who entered cities on warhorses after conquest, Jesus chose a beast of burden—symbolizing peace, not war.

f. “Behold, your King is coming to you” – The wording is both triumphant and personal. Israel’s true King was not distant or detached—He was coming to them. But not all would receive Him. Though He fulfilled Scripture openly and unmistakably, the religious leaders remained blind (John 1:11). Yet this moment also perfectly aligned with Daniel’s prophetic timeline. Many conservative scholars believe this fulfilled Daniel 9:25 “to the day,” marking the 483rd year since the decree to rebuild Jerusalem under Artaxerxes in 445 B.C. (see Sir Robert Anderson's calculations in The Coming Prince).

g. “So the disciples went and did as Jesus commanded them” – This obedience reflects the growing trust of the disciples. They did not question or argue, even though the task may have seemed odd or presumptuous. True discipleship often requires unquestioning obedience, especially when God’s commands appear counterintuitive.

2. Matthew 21:7–11 – Jesus Receives and Encourages Adoration as the Messiah

“They brought the donkey and the colt, laid their clothes on them, and set Him on them. And a very great multitude spread their clothes on the road; others cut down branches from the trees and spread them on the road. Then the multitudes who went before and those who followed cried out, saying:
‘Hosanna to the Son of David!
“Blessed is He who comes in the name of the Lord!”
Hosanna in the highest!’
And when He had come into Jerusalem, all the city was moved, saying, ‘Who is this?’
So the multitudes said, ‘This is Jesus, the prophet from Nazareth of Galilee.’” (Matthew 21:7–11, NKJV)

a. “They brought the donkey and the colt, laid their clothes on them, and set Him on them” – The disciples obeyed Jesus’ instruction exactly. They brought both animals and prepared them as a royal mount. Though Matthew mentions both donkey and colt, Jesus rode only the colt (see Mark 11:2; Luke 19:35; John 12:14), the younger, unbroken animal—a powerful testimony to Christ’s authority over nature. The laying of garments on the animal reflected an act of submission and honor, a makeshift saddle expressing loyalty and reverence.

b. “A very great multitude spread their clothes on the road; others cut down branches from the trees and spread them on the road” – This was a royal welcome. Spreading garments and palm branches created a “carpeted” path for the King. These gestures were rooted in Jewish tradition as symbols of homage and victory. In 2 Kings 9:13, when Jehu was declared king, the people laid their garments under him. Likewise, palm branches were connected with national deliverance (see 1 Maccabees 13:51; 2 Maccabees 10:7) and ultimately point to the eternal praise of Christ in Revelation 7:9.

c. “Hosanna to the Son of David!” – This is an unmistakable public declaration that Jesus was the Messiah. “Hosanna” is derived from the Hebrew hoshi‘a na—meaning “save now” (Psalm 118:25). It had become a cry of praise and welcome for the coming King. The phrase “Son of David” acknowledges Jesus as the rightful heir to the Davidic throne (2 Samuel 7:12–16; Isaiah 11:1), fulfilling Messianic expectations. The phrase “He who comes in the name of the Lord” comes from Psalm 118:26—a Messianic psalm sung during Passover.

This public praise was not only accepted by Jesus—it was orchestrated by Him. Though previously He had often restrained people from proclaiming His identity (Matthew 8:4; Matthew 16:20), now He welcomed it. This was the prophesied day of Daniel 9:25–26, the “presentation day” of Messiah to Israel, and Jesus permitted the honor due to Him.

d. “Hosanna in the highest!” – The crowd’s adoration reached heavenward. They not only praised Jesus on earth but invoked the blessing and approval of heaven. This phrase essentially says, “Let all of heaven join in this praise.” It affirms that this earthly act of worship corresponds to divine truth. The heavenly realm rejoices when Jesus is rightly honored on earth.

e. “And when He had come into Jerusalem, all the city was moved, saying, ‘Who is this?’” – The word translated moved (Greek: seio) is the same word used for earthquakes (Matthew 27:51). The entire city was stirred like a seismic event. Some were amazed; others were confused. But none were indifferent. This dramatic entrance caused a disruption—exactly what true gospel preaching always does (Acts 17:6).

Just as the city had been troubled at the birth of Christ when the wise men arrived (Matthew 2:3), now it trembled again as the King publicly arrived. Yet the question, “Who is this?” shows that despite all His miracles and teachings, many still did not recognize who He truly was.

f. “So the multitudes said, ‘This is Jesus, the prophet from Nazareth of Galilee.’” – The crowd responded with a partial truth. They recognized Jesus as a prophet and His Galilean origin, but they missed the fullness of His identity as Messiah and Son of God. This statement reflects limited spiritual insight, much like in Matthew 16:14 when people saw Jesus as merely one of the prophets.

Though Jesus had been born in Bethlehem (fulfilling Micah 5:2), He was commonly associated with Nazareth, a city often despised (John 1:46). This again shows the irony of God’s redemptive plan: the King of Glory would be known by the name of a humble, backwater town. Yet even this fulfilled prophecy, for Matthew 2:23 says, “He shall be called a Nazarene.”

B. Jesus Cleanses the Temple

1. Matthew 21:12–13 – Jesus Forcibly Stops the Commercial Desecration of the Temple

“Then Jesus went into the temple of God and drove out all those who bought and sold in the temple, and overturned the tables of the money changers and the seats of those who sold doves. And He said to them, ‘It is written, “My house shall be called a house of prayer,” but you have made it a “den of thieves.”’” (Matthew 21:12–13, NKJV)

Jesus enters the temple courts with divine authority and righteous indignation. This act, distinct from the temple cleansing early in His ministry (John 2:13–22), is a deliberate and final confrontation with a corrupt religious system. His actions are not rash, but premeditated and prophetic. He drove out both the buyers and the sellers — indicating that He condemned not only those who profited from the sacrificial system but also those complicit in sustaining it.

The phrase “overturned the tables of the money changers and the seats of those who sold doves” reveals that the temple courts — especially the Court of the Gentiles — had become a corrupt marketplace. The money changers exchanged Roman currency (considered unclean for temple use) for Jewish shekels at extortionate rates. Sellers of doves, often purchased by the poor (Leviticus 5:7), likewise gouged prices. Barclay notes that doves could cost 4 pence outside the temple and up to 75 pence inside, almost 20 times the market rate.

Jesus’ zeal reflects Malachi 3:1–3, where the Lord comes suddenly to His temple and purifies the sons of Levi. It also fulfills messianic expectations that the Christ would cleanse the temple — not from Gentiles or pagans, but from hypocrisy and corruption among the people of Israel themselves.

“It is written, ‘My house shall be called a house of prayer,’ but you have made it a ‘den of thieves.’” — This is a conflation of Isaiah 56:7 and Jeremiah 7:11. In Isaiah 56:7, the Lord says, “Even them I will bring to My holy mountain, and make them joyful in My house of prayer… For My house shall be called a house of prayer for all nations.” Jesus confronts the fact that this place of worship — especially the only area where Gentiles were permitted to approach the Lord — had been turned into a place of commerce and greed, thus robbing the nations of access to God.

The reference to “den of thieves” from Jeremiah 7:11 is devastating. There, the prophet denounces the people for trusting in the temple while living in rebellion. Jesus is drawing a direct line: the temple had become a sanctuary for robbers, not worshippers — a place of refuge for sin rather than repentance.

As Spurgeon rightly notes, no man-made institution, parliamentary act, or religious reform can cleanse the temple. Only Christ Himself — the one whose hands were pierced — has the authority to purify His house.

2. Matthew 21:14 – Jesus Carries on God’s Compassionate Work in the Temple Courts

“Then the blind and the lame came to Him in the temple, and He healed them.” (Matthew 21:14, NKJV)

After purging the temple of corruption, Jesus immediately turns to acts of healing and mercy. The blind and the lame, who were forbidden from drawing near to the altar (see Leviticus 21:17–23), now find healing and access in the very courts previously occupied by merchants. Christ is restoring the temple to its proper use — not a place of exclusion or profit, but of access to God through the work of the Messiah.

This is a vivid expression of Isaiah 35:5–6: “Then the eyes of the blind shall be opened, and the ears of the deaf shall be unstopped. Then the lame shall leap like a deer.” The healing of the outcasts follows judgment on the hypocrites — a divine pattern repeated throughout Scripture. His judgment clears the way for grace.

Moreover, Jesus did not form a political movement or social justice ministry after this cleansing. He resumed His messianic work — preaching, healing, and drawing people to Himself in fulfillment of His mission (Luke 4:18–19).

3. Matthew 21:15–17 – The Indignation of the Jewish Leaders

“But when the chief priests and scribes saw the wonderful things that He did, and the children crying out in the temple and saying, ‘Hosanna to the Son of David!’ they were indignant and said to Him, ‘Do You hear what these are saying?’ And Jesus said to them, ‘Yes. Have you never read, “Out of the mouth of babes and nursing infants You have perfected praise”?’ Then He left them and went out of the city to Bethany, and He lodged there.” (Matthew 21:15–17, NKJV)

The chief priests and scribes, instead of rejoicing in the healings and restoration taking place in the temple, become indignant at the praise Jesus is receiving. They ignore the miracles and resent the adoration. The children cry out “Hosanna to the Son of David!” — a clear messianic title. The leaders demand that Jesus rebuke them. Instead, Jesus affirms them.

“Out of the mouth of babes and nursing infants You have perfected praise” – Jesus quotes Psalm 8:2, which reads: “Out of the mouth of babes and nursing infants You have ordained strength, because of Your enemies, that You may silence the enemy and the avenger.” By doing so, He declares that even the smallest and least regarded among men can be used by God to declare truth — and to shame the arrogant.

Spurgeon notes that children are not sanctified by becoming little adults; rather, their praise in their own childlike way is pleasing to God. The Lord doesn’t need the approval of religious elites to receive praise; He accepts it from the humble and the lowly — and this includes children.

The religious leaders, in contrast, reveal their hypocrisy. They were not outraged by the desecration of the temple, but by the exaltation of Jesus.

Finally, Jesus departs for Bethany, likely to the home of Mary, Martha, and Lazarus. His public work in Jerusalem for that day is complete. He has cleansed the temple, healed the broken, received pure praise, and confronted corruption. The King has declared His authority — both over the temple and over the worship offered there.

C. The Lesson of the Fig Tree

1. Matthew 21:18–19 – Jesus Rebukes a Fig Tree

“Now in the morning, as He returned to the city, He was hungry. And seeing a fig tree by the road, He came to it and found nothing on it but leaves, and said to it, ‘Let no fruit grow on you ever again.’ Immediately the fig tree withered away.” (Matthew 21:18–19, NKJV)

As Jesus returned to Jerusalem from Bethany in the morning, He experienced hunger. Some have questioned how He could be hungry when He had likely stayed at the home of Martha, Mary, and Lazarus. Charles Spurgeon offers the insight that perhaps Jesus had risen early to commune with His Father and had not yet eaten, reminding us that He was truly human and shared in our bodily limitations. G. Campbell Morgan adds, “He was perfectly human and therefore physically hungry, for hunger is a sign of health.”

Seeing a fig tree in leaf, Jesus approached it expecting to find fruit. However, there were no figs—only leaves. This fig tree had the appearance of fruitfulness but no real substance. Fig trees in that region normally bore fruit before or alongside their leaves, so its leafy appearance was a deceptive signal of productivity.

Jesus then pronounced judgment: “Let no fruit grow on you ever again.” Immediately the fig tree withered. This is one of the very few destructive miracles performed by Jesus, and notably, like the drowning of the pigs in Matthew 8:30–32, it was not directed at people but served as a profound and symbolic teaching.

The fig tree stood as a symbol of national Israel—professing righteousness, adorned with outward signs of religious life, but ultimately barren. It had leaves, but no fruit. In that acted-out parable, Jesus was declaring judgment upon a nation that had the form of godliness but denied its power (see 2 Timothy 3:5). As Spurgeon remarked, “The first Adam came to the fig tree for leaves, but the Second Adam looks for figs.”

This rebuke warned of the coming judgment upon those who, like Israel’s religious leaders, put forth a show of piety but bore no spiritual fruit. As R.T. France wrote, “The story is clear and simple, and its point obvious—that what counts is not promise but performance.”

2. Matthew 21:20–22 – How Did Jesus Do This?

“And when the disciples saw it, they marveled, saying, ‘How did the fig tree wither away so soon?’ So Jesus answered and said to them, ‘Assuredly, I say to you, if you have faith and do not doubt, you will not only do what was done to the fig tree, but also if you say to this mountain, “Be removed and be cast into the sea,” it will be done. And whatever things you ask in prayer, believing, you will receive.’” (Matthew 21:20–22, NKJV)

When the disciples saw how quickly the fig tree had withered, they were astonished. Their question was not merely about the event itself but the spiritual power behind it. Jesus explained that this miracle was the result of faith expressed through prayer. He shifted the focus from the miracle to the lesson behind it—that the same kind of faith that pronounced judgment on the fig tree could accomplish even greater things.

He said, “Assuredly, I say to you, if you have faith and do not doubt…” This was not hyperbole. Jesus was teaching them the power of genuine, unwavering faith, the kind that believes God and acts on His promises. This kind of faith doesn’t stop at admiration; it moves mountains—literally and figuratively.

The phrase, “if you say to this mountain, ‘Be removed and be cast into the sea,’ it will be done,” may have pointed to the Mount of Olives or possibly to the Temple Mount, both visible from where they were standing. The mountain represents any obstacle or impossibility standing in the way of God's will. Faith, when rooted in the promises of God and free from doubt, aligns with God’s purposes and releases divine authority.

Jesus concludes with a powerful promise: “And whatever things you ask in prayer, believing, you will receive.” This statement is made to His disciples, not to the crowds. It is a conditional promise—rooted in faith, prayer, and a submitted heart. The believer must be walking in fellowship with God, praying according to His will (1 John 5:14–15), and believing without doubting.

Matthew Henry said, “Faith must rest upon a promise. Nothing is too great for the prayer of faith, but that prayer must proceed from a heart fully surrendered to God’s will.” Likewise, F.B. Meyer explained that true faith arises when there is deep communion with God: “We can only believe for a thing when we are in such union with God that His thought and purpose can freely flow into us, suggesting what we should pray for, and leading us to that point in which there is perfect sympathy and understanding between us and the divine mind. Faith is always the product of such a frame as this.”

D. Jesus Answers the Jewish Leaders

1. (Matthew 21:23-27) Jesus is confronted by the chief priests and elders in the temple as He teaches.

"Now when He came into the temple, the chief priests and the elders of the people confronted Him as He was teaching, and said, 'By what authority are You doing these things? And who gave You this authority?' But Jesus answered and said to them, 'I also will ask you one thing, which if you tell Me, I likewise will tell you by what authority I do these things: The baptism of John—where was it from? From heaven or from men?' And they reasoned among themselves, saying, 'If we say, “From heaven,” He will say to us, “Why then did you not believe him?” But if we say, “From men,” we fear the multitude, for all count John as a prophet.' So they answered Jesus and said, 'We do not know.' And He said to them, 'Neither will I tell you by what authority I do these things.'"

Jesus was undeterred by their challenge. The religious leaders had been humiliated the day before when Jesus overturned the money tables and declared God’s house to be a house of prayer, not a den of thieves. Now they came with a confrontational challenge, demanding to know what authority He had for these actions. But Jesus, wise in discernment and sovereign in His approach, turned the tables on them with a counter-question about John the Baptist’s baptism. The reason was simple: if they could not or would not recognize the divine origin of John’s ministry, they were unqualified to judge the divine authority behind Jesus' own ministry. Their refusal to answer truthfully revealed their hypocrisy and cowardice, as they feared the crowd rather than fearing God. Because of their refusal to answer in truth, Jesus refused to dignify their question with an answer.

1. (Matthew 21:28-32) The parable of the two sons.

“But what do you think? A man had two sons, and he came to the first and said, ‘Son, go, work today in my vineyard.’ He answered and said, ‘I will not,’ but afterward he regretted it and went. Then he came to the second and said likewise. And he answered and said, ‘I go, sir,’ but he did not go. Which of the two did the will of his father?” They said to Him, “The first.” Jesus said to them, “Assuredly, I say to you that tax collectors and harlots enter the kingdom of God before you. For John came to you in the way of righteousness, and you did not believe him; but tax collectors and harlots believed him; and when you saw it, you did not afterward relent and believe him.”

In this parable, Jesus exposed the hypocrisy of the religious leaders. The first son initially rebelled but later repented and obeyed. The second son gave lip service to obedience but never followed through. The lesson is that genuine repentance is demonstrated by action, not words. The tax collectors and harlots were like the first son—they initially rejected God’s ways, but upon hearing the truth from John the Baptist, they repented and obeyed. The chief priests and elders, however, were like the second son—outwardly religious and respectful, but inwardly rebellious and disobedient. Jesus made it clear: outward piety without inward obedience is meaningless, and those who genuinely repent—even from the lowest social standing—will enter the kingdom of God ahead of self-righteous religious leaders.

1. (Matthew 21:33-41) The parable of the wicked vinedressers.

“Hear another parable: There was a certain landowner who planted a vineyard and set a hedge around it, dug a winepress in it and built a tower. And he leased it to vinedressers and went into a far country. Now when vintage-time drew near, he sent his servants to the vinedressers, that they might receive its fruit. And the vinedressers took his servants, beat one, killed one, and stoned another. Again he sent other servants, more than the first, and they did likewise to them. Then last of all he sent his son to them, saying, ‘They will respect my son.’ But when the vinedressers saw the son, they said among themselves, ‘This is the heir. Come, let us kill him and seize his inheritance.’ So they took him and cast him out of the vineyard and killed him. Therefore, when the owner of the vineyard comes, what will he do to those vinedressers?” They said to Him, “He will destroy those wicked men miserably, and lease his vineyard to other vinedressers who will render to him the fruits in their seasons.”

This parable clearly mirrors Israel’s history. The vineyard represents Israel, the landowner is God, the vinedressers are the religious leaders, and the servants are the prophets who were repeatedly sent and mistreated throughout Israel’s history. The climax of the parable—the killing of the landowner’s son—is a clear allusion to the coming crucifixion of Jesus Christ, the Son of God. The reaction of the hearers is telling: they pronounce judgment on themselves by acknowledging that such wicked tenants should be destroyed and replaced. Jesus was foretelling the removal of authority from the current religious leadership and its transfer to the apostles and the future church, made up of Jews and Gentiles who would produce spiritual fruit.

1. (Matthew 21:42-46) Jesus applies the parable and warns the leaders.

"Jesus said to them, 'Have you never read in the Scriptures:

"The stone which the builders rejected
Has become the chief cornerstone.
This was the Lord’s doing,
And it is marvelous in our eyes"?

Therefore I say to you, the kingdom of God will be taken from you and given to a nation bearing the fruits of it. And whoever falls on this stone will be broken; but on whomever it falls, it will grind him to powder.' Now when the chief priests and Pharisees heard His parables, they perceived that He was speaking of them. But when they sought to lay hands on Him, they feared the multitudes, because they took Him for a prophet."

Jesus quoted Psalm 118:22–23 to declare that the stone rejected by the builders—Himself—would become the chief cornerstone. Though rejected by the religious elite, Jesus was in fact chosen and exalted by God. The kingdom would be taken from those religious leaders who failed to bear fruit and given to those who would. Those who oppose the cornerstone will either be broken in repentance or crushed in judgment. The leaders understood that the parables condemned them, yet rather than repenting, they hardened their hearts further. Still, they dared not seize Jesus yet, for the people held Him in high regard as a prophet.