This story is also recorded in Mk 10:46-52 and Lk 18:35-43. It is the story of the healing of two blind men as Jesus was traveling to Jerusalem in preparation for his death.
(Mat 20:29) And as they departed from Jericho, a great multitude followed him.
Lk 18:35 says “come nigh unto Jericho.” Is this a contradiction? No. There were two Jericho’s. In Jos 6, Jericho was destroyed. In Jos 6:26 there was a curse pronounced upon the man that rebuilt the city. In 1 Ki 16:34, Jericho was rebuilt by Hiel. Evidently, it was destroyed again by Nebuchadnezzar. According to Jer 52:8, Jericho is where the Chaldeans caught Zedekiah. A Roman Jericho was built later in the near vicinity. Mark and Matthew evidently refer to the old Jericho, the ruins of which have been discovered, while Luke is talking about the new Roman Jericho. The two blind men were apparently between the two towns. In Kentucky there are two towns both called Pleasureville (Old Pleasureville and New Pleasureville).
(Mat 20:30) And, behold, two blind men sitting by the way side, when they heard that Jesus passed by, cried out, saying, Have mercy on us, O Lord, thou son of David.
Two blind men. Mk 10:46 only mentions Bartimaeus. Lk 18:35 mentions only a certain blind man. This is like Mk 5:1-2, where one man is mentioned in the tombs while Matt 8:28 reveals that there were two.
Have mercy on us. They knew to cry for his mercy from Matt 9:27-31 which took place near Capernaum. Jesus had healed blind men like this before. This is similar to the people touching the hem of Jesus’ garment based on the testimony of the woman who touched his garment before (Matt 9:20 and 14:36).
Thou son of David. This title shows that they knew Jesus was more than just “Jesus of Nazareth,” (Lk 18:37); he was the Messiah (Matt 1:1). They would have known him as the Messiah by his works (Matt 12:22-23). The Pharisees should have known by the scripture (Matt 22:42).
(Mat 20:31) And the multitude rebuked them, because they should hold their peace: but they cried the more, saying, Have mercy on us, O Lord, thou son of David.
Hold their peace. They were creating a ruckus. Beggars have a way of being pushy and persistent when they beg. Their determination often causes people to want to push them away.
(Mat 20:32) And Jesus stood still, and called them, and said, What will ye that I shall do unto you?
He gave them a blank check like he did to Solomon (1 Ki 3:5, 9). Solomon asked for understanding. The spiritual request was the best request. Likewise, the blind men asked for sight not money.
(Mat 20:33) They say unto him, Lord, that our eyes may be opened.
Notice the strange contrast to Gen 3:5-7. Compare Jn 9:10-11 and Jn 9:39-41. The opening of the eyes of as a result of sin caused blindness in sinners (2 Cor 4:3-4). The blindness of Bartimaeus didn’t destroy his perception, though. Look at Lk 18:37 and contrast this with verse 38. Those who could see only saw Jesus of Nazareth. Those who couldn’t see saw Jesus the son of David. They could “see” without natural eyes.
(Mat 20:34) So Jesus had compassion on them, and touched their eyes: and immediately their eyes received sight, and they followed him.
A touch was often associated with the healing of the blind (Matt 9:29; Jn 9:6). Notice the similarity to the new birth. The sight was immediate and the new birth is immediate. They followed him and we should, too, after we have been born again. The Lord gave them the option to go their way but they went his way instead. They were never the same after the healing. We call Bartimaeus “blind Bartimaeus.” But after the healing he was never blind again; and after the new birth, we are never the same (2 Cor 5:17, we are new creatures).