What does Matthew 27:38 mean?
ESV: Then two robbers were crucified with him, one on the right and one on the left.
NIV: Two rebels were crucified with him, one on his right and one on his left.
NASB: At that time two rebels *were being crucified with Him, one on the right and one on the left.
CSB: Then two criminals were crucified with him, one on the right and one on the left.
NLT: Two revolutionaries were crucified with him, one on his right and one on his left.
KJV: Then were there two thieves crucified with him, one on the right hand, and another on the left.
Verse Commentary:
Two men were executed alongside Jesus, one on each side (Matthew 27:31–35; Luke 23:32). The Greek word used for robbers here, lēstai, was occasionally used in this era for revolutionaries. Some scholars believe these two men had worked with Barabbas (Luke 23:18) as insurrectionists to overthrow Rome. It's possible the three crosses had been prepared for Barabbas and these two men, and Jesus had taken Barabbas' place in the last-minute switch (Matthew 27:15–23). Other scholars see no reason to read anything else into this Greek word for robbers besides the men being common thieves.

Ultimately, the exact identity of these men is irrelevant. They were criminals, fulfilling the prophecy in Isaiah 53:12 that the Messiah would be put in the same category as criminals. The same verse goes on to say that He "bore the sin of many, and makes intercession for transgressors." Other gospel accounts note that Jesus eventually promised one of these men, who changed his mind and attitude, he would be with Jesus in paradise (Luke 23:43).
Verse Context:
Matthew 27:32–44 describes Jesus' march to the cross, aided by a man named Simon of Cyrene. Jesus is offered a numbing, bitter wine, but refuses it, and is nailed to the cross. Soldiers gamble for His clothes. A somewhat sarcastic sign above Him reads "the King of the Jews." Observers, including several Jewish religious leaders, mock Jesus for not being able to save Himself. Even the criminals being executed on either side of Jesus insult Him. Mark 15:20–32, Luke 23:36–43, and John 19:16–27 cover this same process.
Chapter Summary:
When Judas learns Jesus has been condemned, he regrets betraying the Lord. He throws down his ill-gotten money and hangs himself. Jesus is taken to Pilate, who finds nothing to charge Him with. Given the choice, the people shout for the release of a convicted murderer and insist on Jesus' death. Jesus is mocked by a battalion of soldiers and then taken to be crucified. On the cross, He is mocked for not being able to save Himself. After three hours of darkness, Jesus dies. He is buried by a rich follower in a new tomb. This location is tightly guarded to prevent anyone from stealing the body.
Chapter Context:
Matthew 27 begins with an official meeting of the Jewish ruling council. They affirm Jesus' condemnation from the previous night, described in chapter 26. Judas confesses his betrayal and hangs himself. Pilate tries to release Jesus, but the mob shouts for Jesus to be crucified. Jesus is humiliated by Roman soldiers and marched to be executed. On the cross, He is mocked by Jewish religious leaders and others. He dies and is buried in a never-used tomb. Extensive efforts to secure His body from being stolen only serve to prove the miraculous nature of His resurrection, which is detailed in chapter 28.
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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