What does Matthew 21:7 mean?

It may appear awkward that after walking all the way from Galilee, including the long walk uphill from Jericho to the Mount of Olives and Jerusalem, Jesus would suddenly direct His disciples to get Him a donkey so that He could ride the last mile into Jerusalem. However, Jesus was not tired. He had very specific reason for wanting to enter the city this way (Matthew 21:5). Jesus was delivering what Bible scholars call an "acted parable," demonstrating with His actions instead of using a story to reveal that He is the Messiah.

Many Israelites knew the Scriptures well. After enduring Roman occupation, they were especially familiar with passages that promised the coming of the Messiah to rule and reign over Israel. They knew Zechariah's prophecy addressed to the "daughter of Zion," another name for the city of Jerusalem: "Your king is coming to you…humble, and mounted on a donkey" (Zechariah 9:9). Jesus is intentionally entering the city in this way as a clear statement that He is the Messiah, the promised king. The prophecy not only identifies Messiah, it refers to the nature of His arrival: donkeys are not military animals. Rather than arriving on a horse—as He will in His second, conquering arrival (Revelation 19:11)—Christ will present Himself in a manner of peace.

Most English translations for this verse read a bit awkwardly. The disciples brought the two animals and "put on them their cloaks, and he sat on them." The second "them" means the cloaks, not the donkeys. Jesus did not sit on both the mother donkey and the colt at the same time. He sat on the colt to fulfill Zechariah's words. The disciples put their outer cloaks over the animal so Jesus—and the animal—would be more comfortable.

Mark and Luke don't mention the mother donkey, but they do mention that nobody had ever sat on this colt before (Mark 11:2; Luke 19:30).