Matthew 21:1
When they drew near to Jerusalem, and came to Bet-Pagei, to the Mount of Olives, then Yeshua sent two disciples,

Matthew 21:2
saying to them, Go into the village that is opposite you, and immediately you will find a donkey tied, and a colt with her. Untie them, and bring them to me.

Matthew 21:3
If anyone says anything to you, you shall say, The Lord needs them, and immediately he will send them.

Matthew 21:4
All this was done, that it might be fulfilled which was spoken through the prophet, saying,

Matthew 21:5
Tell the daughter of Zion, behold, your King comes to you, humble, and riding on a donkey, on a colt, the foal of a donkey.

Kol HaTor comments,

“A lowly person, riding on a donkey” – Mashiach ben Yosef is a lowly person ….“I was brought low, and he saved me.” His lowliness protects him from death.”
Kol HaTor 2.114, translated by R’ Yechiel Bar Lev and K. Skaist


Matthew 21:6
The disciples went, and did just as Yeshua commanded them,

Matthew 21:7
and brought the donkey and the colt, and laid their clothes on them; and he sat on them.

The “them” refers to the clothes, which are upon the donkey. The donkey and its link to ‘Shiloh’ is first mentioned in Genesis 49,

“Binding his foal to the vine, his donkey’s colt to the choice vine; he has washed his garments in wine, his robes in the blood of grapes.”
Genesis 49:11

The donkey has been historically linked with Redemption. Samson fought the battles of HaShem with the jawbone of a donkey (Judges 15:15), and King David went to face Goliath of Gath with a donkey,

“Jesse took a donkey loaded with bread, and a bottle of wine, and a young goat, and sent them by David his son to Saul.”
1 Samuel 16:20

The central message of redemption occurs in Genesis 22, which speaks of the Akedat Yitzchak in connection with the donkey,

“Abraham rose early in the morning, and saddled his donkey, and took two of his young men with him, and Isaac his son. He split the wood for the burnt offering, and rose up, and went to the place of which God had told him.”
Genesis 22:3

donkey-316467_1280Moshe’s return to Israel is connected with a donkey,

“Moses took his wife and his sons, and set them on the donkey, and he returned to the land of Egypt…”
Exodus 4:20

Interestingly, the Hebrew of Exodus 4 does not say “A donkey” but rather “THE donkey.” Rashi comments on this detail,

על החמר: חמור המיוחד, הוא החמור שחבש אברהם לעקידת יצחק והוא שעתיד מלך המשיח להגלות עליו, שנאמר (זכריה ט ט) עני ורוכב על חמור

“On the donkey. The particular donkey. It is the donkey that Abraham saddled for the binding of Isaac, and it is the one that Messiah, the King, is destined to be revealed upon, as it says, “a humble man, riding on a donkey.”
Rashi to Exodus 4:20, Mesorah Publishers pg. 37, cf. Pirkei de-Rebbi Eliezer 31

Rashi is citing Zechariah 9:9,

“Rejoice greatly, daughter of Zion! Shout, daughter of Jerusalem! Behold, your King comes to you! He is righteous, and having salvation; lowly, and riding on a donkey, even on a colt, the foal of a donkey.”
Zechariah 9:9

The Talmud comments,

“R. Alexandri said: R. Joshua b. Levi pointed out a contradiction. it is written, in its time [will the Messiah come], whilst it is also written, I [the Lord] will hasten it! — if they are worthy, I will hasten it: if not, [he will come] at the due time. R. Alexandri said: R. Joshua opposed two verses: it is written, And behold, one like the son of man came with the clouds of heaven34 whilst [elsewhere] it is written, [behold, thy king cometh unto thee . . . ] lowly, and riding upon an donkey! If they are meritorious, [he will come] with the clouds of heaven; if not, lowly and riding upon an donkey.”
Sanhedrin 98a, Soncino Press Edition

The Siddur says,

“With the coming and arrival of the season of God’s love…the gazelle (God) observed through the lattice windows, and applied a cure to the bloodied nation. He leaped across time to peform wonders and to multiply new commandments upon the old…From the beginning the Lord established Nissan as the first, but He did not reveal its understanding in the book possessed by Adam…it was sanctified at its beginning, after a third [the tenth of Nissan], in its middle and after its majority to observe, to sanctify the new moon, to take a lamb for the Pesach…its beginning is reserved in every generation, for the coming of the pauper riding on a donkey [Messiah]…”
Yotzer for Parashas HaChodesh, Artscroll Nusach Sefard Siddur, Mesorah Publishers, pg. 949

The Maharal, R’ Judah Loew ben Betzalel (1520 CE – 1609 CE) comments on this passage in connection with the donkey (chamor),

“It is reasonable to ask how this donkey is different from others – why does the Torah single this one out? A donkey is a donkey! The midrash points out that this donkey was created at twilight; it is the donkey that Moshe rode, and it is the one that will ultimately be ridden by the son of David. . . the rabbis wanted to juxtapose Avraham, Moshe and Mashiach, who had what no other creations had – a special exalted status. . . As for the Mashiach, the prophet says, “Behold my servant shall succeed, he will be exalted and become high and exceedingly lofty” [Isaiah 52:13]. The midrash interprets: “exalted” – more than Avraham; ‘high’ – even more than Moshe; and ‘exceedingly lofty’ – more than the ministering angels [Tanchuma, Toldot 14]. Only these three are loftier than time, space and the universe…The donkey is the only non-kosher animal specified forth performance of a commandment – its firstborn must be redeemed. Chamor [donkey] gets its name from chomri [physical, material]…Kings reign over the material world, which is symbolically represented by the image of a man riding an animal. These three spiritual kings – Avraham, Moshe and Mashiach – who ascend to the highest levels of spirituality, symbolically ride the donkey, which represents the material world. A horse would, as a rule, be more fitting for a king, but these are spiritual kings…”
Maharal of Prague, Gur Arye, on Exodus and Leviticus, translated by Moshe David Kuhr, Gefen Publishers, pgs. 34-35 

Matthew 21:8
A very great multitude spread their clothes on the road. Others cut branches from the trees, and spread them on the road.


Matthew 21:9
The multitudes who went before him, and who followed kept shouting, Hoshia’na to the son of David! Blessed is he who comes in the name of the Lord! Hoshia’na in the highest!


Matthew 21:10
When he had come into Jerusalem, all the city was stirred up, saying, Who is this?


Matthew 21:11
The multitudes said, This is the prophet, Yeshua, from Nazareth of Galilee.


Matthew 21:12
Yeshua entered into the Temple of God, and drove out all of those who sold and bought in the temple, and overthrew the money changers tables and the seats of those who sold the doves.


Matthew 21:13
He said to them, “It is written, My house shall be called a house of prayer, but you have made it a den of robbers!”


Matthew 21:14
The blind and the lame came to him in the temple, and he healed them.


Matthew 21:15
But when the chief priests and the scribes saw the wonderful things that he did, and the children who were crying in the temple and saying, Hoshia’na to the son of David! they were indignant,


Matthew 21:16
and said to him, Do you hear what these are saying? Yeshua said to them, Yes. Did you never read, Out of the mouth of babes and nursing babies you have perfected praise?


Matthew 21:17
He left them, and went out of the city to Bethany, and lodged there.


Matthew 21:18
Now in the morning, as he returned to the city, he was hungry.

“Misery is mine! Indeed, I am like one who gathers the summer fruits, as gleanings of the vineyard: There is no cluster of grapes to eat. My soul desires to eat the early fig.”
Micah 7:1

Matthew 21:19
Seeing a fig tree by the road, he came to it, and found nothing on it but leaves. He said to it, Let there be no fruit from you forever! Immediately the fig tree withered away.

“He spoke this parable. “A certain man had a fig tree planted in his vineyard, and he came seeking fruit on it, and found none.  He said to the vine dresser, ‘Behold, these three years I have come looking for fruit on this fig tree, and found none. Cut it down. Why does it waste the soil?’  He answered, ‘Lord, leave it alone this year also, until I dig around it, and fertilize it.  If it bears fruit, fine; but if not, after that, you can cut it down.’”
Luke 13:6-9

“Don’t think to yourselves, ‘We have Abraham for our father,’ for I tell you that God is able to raise up children to Abraham from these stones. “Even now the axe lies at the root of the trees. Therefore, every tree that doesn’t bring forth good fruit is cut down, and cast into the fire.”
Matthew 3:7-10


Matthew 21:20
When the disciples saw it, they marveled, saying, How did the fig tree immediately wither away?


Matthew 21:21
Yeshua answered them, Most certainly I tell you, if you have faith, and do not doubt, you will not only do what was done to the fig tree, but even if you told this mountain, Be taken up and cast into the sea, it would be done.


Matthew 21:22
All things, whatever you ask in prayer, believing, you will receive.


Matthew 21:23
When he had come into the temple, the chief priests and the elders of the people came to him as he was teaching, and said, By what authority do you do these things? Who gave you this authority?


Matthew 21:24
Yeshua answered them, I also will ask you one question, which if you tell me, I likewise will tell you by what authority I do these things.


Matthew 21:25
The immersion of Yochanan, where was it from? From heaven or from men? They reasoned with themselves, saying, If we say, From heaven, he will ask us, Why then did you not believe him?


Matthew 21:26
But if we say, From men, we fear the multitude, for all hold Yochanan as a prophet.


Matthew 21:27
They answered Yeshua, and said, We don’t know. He also said to them, Neither will I tell you by what authority I do these things.


Matthew 21:28
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.


Matthew 21:29
He answered, I will not, but afterward he changed his mind, and went.


Matthew 21:30
He came to the second, and said the same thing. He answered, I go, sir, but he didn’t go.


Matthew 21:31
Which of the two did the will of his father? They said to him, The first. Yeshua said to them, Most certainly I tell you that the tax collectors and the prostitutes are entering into the Kingdom of God before you.


Matthew 21:32
For Yochanan came to you in the way of righteousness, and you didn’t believe him, but the tax collectors and the prostitutes believed him. When you saw it, you didn’t even repent afterward, that you might believe him.

Matthew 21:33
Hear another parable. There was a man who was a master of a household, who planted a vineyard, set a hedge about it, dug a winepress in it, built a tower, leased it out to farmers, and went into another country.

Yeshua draws the imagery from the book of Isaiah,

“Let me sing for my beloved my love song concerning his vineyard: My beloved had a vineyard on a very fertile hill. He dug it and cleared it of stones, and planted it with choice vines; he built a watchtower in the midst of it, and hewed out a wine vat in it; and he looked for it to yield grapes, but it yielded wild grapes.”
Isaiah 5:1-2, ESV

The Midrash says,

“R. Jose the Galilean said: [Let me tell you a] parable: To what may this be likened? To a king of flesh and blood who had a garden in which he built a tall tower. he showed affection for the garden by assigning workmen to it, and ordered them to busy themselves with its cultivation. The king thereupon ascended to the top of the tower, from which he could see them but they could not see him, as it is said, ‘But the L-rd is in His holy temple, be silent before him all the earth’ (Hab. 2:20). At the day’s end the king came down and sat in judgment upon them saying, “Let the tillers come forward and receive their wages, let the hoers come forward and receive their wages,”…[until] there remained workmen who had done no work at all. the king asked, “These, what did they do?” … “Let those who have done my work receive their wages, but those who did not do my work, let them be taken out and executed, for they have rebelled against my command!”
Midrash on Proverbs, Chapter 16, translated by Burton L. Visotzky, Yale University Press, pg 82


Matthew 21:34
When the season for the fruit drew near, he sent his servants to the farmers, to receive his fruit.


Matthew 21:35
The farmers took his servants, beat one, killed another, and stoned another.


Matthew 21:36
Again, he sent other servants more than the first: and they treated them the same way.


Matthew 21:37
But afterward he sent to them his son, saying, They will respect my son.


Matthew 21:38
But the farmers, when they saw the son, said among themselves, This is the heir. Come, lets kill him, and seize his inheritance.


Matthew 21:39
So they took him, and threw him out of the vineyard, and killed him.

Isaiah says,

“For the vineyard of the Lord of hosts is the house of Israel, and the men of Judah are his pleasant planting; and he looked for justice, but behold, bloodshed; for righteousness, but behold, an outcry!”
Isaiah 5:7, ESV 

Matthew 21:40
When therefore the lord of the vineyard comes, what will he do to those farmers?

Matthew 21:41
They told him, He will miserably destroy those miserable men, and will lease out the vineyard to other farmers, who will give him the fruit in its season.


Matthew 21:42
Yeshua said to them, Did you never read in the Scriptures, The stone which the builders rejected, the same was made the head of the corner. This was from the Lord. It is marvelous in our eyes?


Matthew 21:43
Therefore I tell you, the Kingdom of God will be taken away from you, and will be given to a nation bringing forth its fruit.


Matthew 21:44
He who falls on this stone will be broken to pieces, but on whomever it will fall, it will scatter him as dust.


Matthew 21:45
When the chief priests and the Pharisees heard his parables, they perceived that he spoke about them.


Matthew 21:46
When they sought to seize him, they feared the multitudes, because they considered him to be a prophet.