What does Matthew 27:16 mean?

Pilate has been amazed at Jesus' virtual silence in the face of an onslaught of accusations from the Jewish religious leaders (Matthew 27:11–15). Jesus will simply offer no defense, no resistance. Pilate seems to want to release Jesus, however, perhaps because of what he sees in Jesus. Or perhaps he just wants to spite the Jewish leaders. History depicts Pilate as a cruel and relatively condescending politician, who would eventually be removed from his role for inciting unrest. He's no fool, however. He already knows Jesus is popular (Matthew 21:10–11), and this is a personal feud (Matthew 27:18). His discussions with Jesus showed no threat of insurrection (John 18:36). For a variety of reasons, the governor wants to see Jesus released instead of executed.

Every year at Passover, the governor of Judea would release one prisoner in custody. The choice of which prisoner was up to the crowds, or so it seemed. Pilate takes advantage of this to give the crowds a choice. His idea is to offer someone obviously guilty, and distasteful, assuming the gathering crowd will choose Jesus. If so, he can be done with the matter. What Pilate is about to realize is that the crowd assembling at his court is hostile (Matthew 27:20, 24; Mark 15:11, 15), likely because Jesus' enemies have called them for this purpose.

Matthew mentions another prisoner in custody called Barabbas. Several translations describe Barabbas as "notorious." He was apparently well known, anyway. The other Gospels describe him as an insurrectionist and a murderer (Mark 15:7; Luke 23:19). If he was known for trying to start an uprising against Rome, Barabbas may have been popular with the Jewish people and thought of as a Jewish hero. And yet, in this situation, he was far more guilty of what the religious leader were claiming about Jesus: to be a threat to Roman rule. More than likely, this man was scheduled to be crucified that very day.

Adding intense symbolism to this moment, many manuscripts of Matthew name the guilty prisoner as "Jesus Barabbas," meaning he had the same common given name as Jesus of Nazareth. Pilate is about to offer the people a choice between a Jesus the people know is innocent and one they know is guilty, and they will choose to reject the Messiah (Matthew 27:21–23). In an almost crass way, the world will reject goodness in favor of someone more to their liking.