What does Matthew 27:38 mean?

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).