What does Matthew 21:1 mean?
ESV: Now when they drew near to Jerusalem and came to Bethphage, to the Mount of Olives, then Jesus sent two disciples,
NIV: As they approached Jerusalem and came to Bethphage on the Mount of Olives, Jesus sent two disciples,
NASB: When they had approached Jerusalem and had come to Bethphage, at the Mount of Olives, Jesus then sent two disciples,
CSB: When they approached Jerusalem and came to Bethphage at the Mount of Olives, Jesus then sent two disciples,
NLT: As Jesus and the disciples approached Jerusalem, they came to the town of Bethphage on the Mount of Olives. Jesus sent two of them on ahead.
KJV: And when they drew nigh unto Jerusalem, and were come to Bethphage, unto the mount of Olives, then sent Jesus two disciples,
NKJV: Now when they drew near Jerusalem, and came to Bethphage, at the Mount of Olives, then Jesus sent two disciples,
Verse Commentary:
Jesus and His disciples have been making their way from Galilee to Jerusalem. He has told them that in Jerusalem He will be delivered into the hands of the Jewish religious leaders, turned over to the Gentiles, and crucified, adding that He will be raised on the third day (Matthew 16:21; 17:22; 20:18–19). Now they have nearly arrived at the city.

The previous chapter ended with Jesus and the disciples near Jericho, about a fifteen-mile walk from Jerusalem on a Roman military road that rises about 3,000 feet in elevation. The road was likely crowded with others coming to Jerusalem for the Passover, as well as those who were specifically following Jesus. Bethphage was about a mile from Jerusalem on the eastern slope of the Mount of Olives.

Jesus selects two of the disciples to go into a nearby village and bring Him an animal to ride into the city (Matthew 21:2).
Verse Context:
Matthew 21:1–11 follows Jesus on His final, "triumphal" entry into Jerusalem. He rides on a donkey for the final mile or so to intentionally fulfill a prophecy from Zechariah about the king arriving in Jerusalem. The crowds praise Him as the Messiah, lining His path with branches and their cloaks. They shout out, "Hosanna to the Son of David!" and "Blessed is he who comes in the name of the Lord!" as seen in Psalm 118. The event we now call Palm Sunday stirs up Jerusalem with many people asking who Jesus is.
Chapter Summary:
Jesus fulfills a prophecy from Zechariah about the coming of the king to Jerusalem by riding in on a donkey. The people celebrate and praise Him as the Messiah. Jesus drives the marketers and moneychangers out of the temple and heals some people. He curses a fig tree and tells the disciples nothing will be impossible for them with faith. Jesus forces cowardly and hypocritical religious leaders to back down with a question about John the Baptist. He then exposes their fraudulent spirituality with two parables about vineyards. Jesus applies to Himself a psalm about a rejected stone being made the cornerstone by the Lord.
Chapter Context:
Matthew 21 finds Jesus arriving near Jerusalem after leaving Jericho in the previous chapter. His triumphal entry is accomplished riding a donkey, and to raucous praise, fulfilling a prophecy about the Messiah. Jesus cleanses the marketplace from the temple, heals, and presents lessons about faith and Israel's failed leadership. This leads into further conversations which Matthew compiles from Jesus' interactions with the Pharisees.
Book Summary:
The Gospel of Matthew clearly shows the influence of its writer's background, and his effort to reach a specific audience. Matthew was one of Jesus' twelve disciples, a Jewish man, and a former tax collector. This profession would have required literacy, and Matthew may have transcribed some of Jesus' words as they were spoken. This book is filled with references to the Old Testament, demonstrating to Israel that Jesus is the Promised One. Matthew also includes many references to coins, likely due to his former profession. Matthew records extensive accounts of Jesus' teaching, more than the other three Gospels.
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