I will confess that when I preach on the triumphal entry of Jesus, I usually preach from either Mark’s or Luke’s version. The reason I avoid Matthew’s account is that it looks at first glance that Matthew is saying that Jesus is sitting on two donkeys at the same time. That is too much to explain in a sermon.
Here is the account from Matthew from the HCSB translation.
When they approached Jerusalem and came to Bethphage at the Mount of Olives, Jesus then sent two disciples, telling them, “Go into the village ahead of you. At once you will find a donkey tied there, and a colt with her. Untie them and bring them to Me. If anyone says anything to you, you should say that the Lord needs them, and immediately he will send them.”
This took place so that what was spoken through the prophet might be fulfilled:
Tell Daughter Zion,
“Look, your King is coming to you,
gentle, and mounted on a donkey,
even on a colt,
the foal of a beast of burden.”
The disciples went and did just as Jesus directed them. They brought the donkey and the colt; then they laid their robes on them, and He sat on them. 8 A very large crowd spread their robes on the road; others were cutting branches from the trees and spreading them on the road. Then the crowds who went ahead of Him and those who followed kept shouting:
Hosanna to the Son of David!
He who comes in the name
of the Lord is the blessed One!
Hosanna in the highest heaven!
When He entered Jerusalem, the whole city was shaken, saying, “Who is this?” And the crowds kept saying, “This is the prophet Jesus from Nazareth in Galilee!” (Matthew 21:1-11)
So what exactly is going on here? Is Jesus really riding both the donkey and the colt at the same time? What would that look like?
The key to this is the Zechariah 9:9 passage which this event is the fulfillment of.
Rejoice greatly, Daughter Zion!
Shout in triumph, Daughter Jerusalem!
Look, your King is coming to you;
He is righteous and victorious,
humble and riding on a donkey,
on a colt, the foal of a donkey.
This seems pretty straight forward. The King is to enter into Jerusalem on a donkey, specifically a colt which is a foal of a donkey. Zechariah seems to be speaking about one animal.
Here is how Matthew quotes the Zechariah passage in Greek:
ειπατε τη θυγατρι σιων ιδου ο βασιλευς σου ερχεται σοι πραυς και επιβεβηκως επι ονον και επι πωλον υιον υποζυγιου
The Greek word kai (και) is most often translated “and” but is translated “even” in the HCSB. It seems clear that Matthew does want us to be thinking of two animals even though that is not what the Hebrew of Zechariah 9:9 says. He can do this because the Septuagint does include the kai. Matthew (as with the other New Testament writers) frequently use the Septuagint.
Why would Matthew make things so complicated when he could have had a nice simple story with one donkey?
We need to remember that one of Matthew’s goals is to make it extremely obvious that Jesus is the fulfillment of prophecy. For most authors, a simple citation of Zechariah would have been sufficient. Not for Matthew. Matthew, thinking with a very Jewish mindset is wanting to fulfil the requirement of two witnesses. Matthew does this elsewhere with the healing of the blind men in Matthew 9:27-31, instead of the one blind man in the other Gospels.
So was there one donkey or two?
The accounts of Mark and Luke do not deny that there was a second donkey, they simply ignore it. The actual fulfillment was Jesus riding the colt and that is all Mark and Luke need to mention. Likely Jesus was only riding one donkey, even if the second was there (Matthew would have understood the practical challenges of trying that). What Matthew is interested in is not the riding ability of Jesus but the prophetic significance of the event. We need to read Matthew not just with our own interests but with his theological and literary intentions.