Contrast the two reactions to the blind men with the crowds following Jesus to Jerusalem. The blond men understand who Jesus is, but the crowds do not.
As they travel towards Jerusalem, the mother of James and John made an audacious request on behalf of her sons. Jesus is travelling with a large crowd, although these are Jewish pilgrims going up to Jerusalem rather than entirely his disciples and followers (notice the disciples and the crowd are two things in verse 1).
In Mark 10:46, the blind man is identified as Bartimaeus the son of Timaeus. The name Bartimaeus is Aramaic and means “son of Timai.” He is seated on the way out of Jericho, and later will follow Jesus on his way to Jerusalem. In Matthew, there are two unnamed blind men. Matthew features two blind men in order to highlight the contrast with two disciples who do not fully understand Jesus’s mission.
The blind men hear Jesus is passing by and begin to cry out “Son of David, have mercy on us” (20:30). Matthew omits Mark’s identification of Jesus the Nazarene, perhaps because he will use that same language at the end of the Triumphal Entry (21:11).
The title “Son of David” was a messianic title in the first century. Isaiah 11 describes the messiah as a “branch from the stump of Jesse” and Jeremiah 23:5-6 says in the coming days the Lord will “raise up for David a righteous branch” to reign as king. The Dead Sea Scrolls use similar language. 4Q252 v.3-4 connects Gen 49:10 (the scepter shall not depart from Judah) with the “messiah of righteousness,” the righteous branch of David. “Until the messiah of righteousness comes, the branch of David. For to him and to his descendants has been given the covenant of the kingship of his people for everlasting generations.” LXX Isaiah 30:19 reads slightly different than the MT: “Because a holy people will reside in Zion, and Jerusalem has wept with weeping, ‘Have mercy on me!’” (Lexham LXX).
The reaction of the crowd traveling with Jesus is surprising. Many in the crowd rebuke the man, trying to silence him, but Jesus calls for him and asks what he can do for him (20:31). In Matthew 19:13 the disciples rebuke the people trying to get children to Jesus, here in Matthew 20:31 the crowd rebukes some beggars for trying to annoy Jesus. “One supposes that the crowd, hardened to roadside beggars, thinks the man a nuisance” (Davies and Allison, Matthew, 3:107).
It is perhaps ironic that the crowds want to silence the beggars, even though they are correctly identifying Jesus as the son of David and perhaps even correct about his being the Branch, the Messiah from Isaiah 11:1. Throughout the gospel Jesus has tried to silence those who identified him as the Messiah, the son of God. Now Jesus does not silence the blind man.
Jesus Heals the two blind men (Matthew 20:32-34). First, he asks what they want (20:32). Jesus’s question is the same as the previous story, James and John approached Jesus to beg a favor (what do you want? Matt 20:21). Just as Peter’s blindness was evident after the healing of the blind man in Mark 8:22-26, now James and John’s blindness is evident just before the restoration of sight to this blind man.
Matthew is intentionally contrasting the (arrogant) request from James and John with the (humble) request of these two blind beggars. “One wonders whether there might not be a lesson intended in the juxtaposition of 20:20–8 and 20:29–34. In the former, two privileged insiders (James and John) make a request through a third party (their mother). The request is prefaced by no title of respect or majesty, it concerns the eschatological” (Davies and Allison, Matthew, 3:110).
They ask for their sight to be restored, so Jesus heals them (20:33-34a). Jesus responds, “in pity.” The aorist passive participle from σπλαγχνίζομαι indicates he was “moved with compassion.” Jesus looked on the crowds in Matthew 9:36; In Matthew 14:14 Jesus has compassion on the crowds and heals their sick; the same verb is used on Luke in the parable of the Good Samaritan (he was moved with compassion for the injured man, Luke 10:33) and the parable of the Prodigal Son (the father was moved with compassion for his son when he returned, Luke 15:20)
This restoration of sight is a parabolic miracle. The crowd traveling with Jesus are blind to who Jesus really is. Even James and John do not fully see clearly who Jesus is, the suffering servant (the son of Man, the Branch, the son of David). Even though the crowd will worship Jesus as the coming king who fulfills prophecy in a few hours. Jesus is about to enter Jerusalem as the King, yet everyone he meets in the next few chapters is blind to who is, ultimately, they will reject him and attempt to ultimately silence him by executing him.
What is the point of this story? Why does it appear just before the Triumphal Entry? A hint might be in the comparison between this story and Matthew 8:4 and 9:3. In both of those miracle stories, Jesus tells people to say nothing., Yet now he allows the blind men to call him son of David openly. Jesus and his disciples are heading directly from Jericho to Jerusalem and the Triumphal Entry is next story in Matthew. The story of these two blind men anticipates that clear announcement of Jesus as messiah