Matthew 27:15-16 meaning

Mark 15:6-7, Luke 23:17 and 23:19 and John 18:40b are the parallel Gospel accounts of this event.

Matthew interrupts his summary account of Jesus's civil trial to make an important interjection. The Gospel writer strategically places this interjection between his account of the first phase of Jesus's civil trial and his account of the third phase of Jesus's civil trial. Matthew, Mark, and John all skip the second phase of Jesus's civil trial, which was His hearing before Herod Antipas—Luke's Gospel is the only one that gives a detailed record of the second phase (Luke 23:8-12). 

The three phases of Jesus's civil trial were:

1. Jesus's Arraignment before Pilate
   (Matthew 27:1-2, 11-14, Mark 15:1-5, Luke 23:1-7, John 18:28-38)
2. Jesus's Audience before Herod Antipas
   (Luke 23:8-12)
3. Pilate's Judgment
   (Matthew 27:15-26, Mark 15:6-15, Luke 23:13-25, John 18:38 - 19:16)

Matthew interjects: Now at the feast the governor was accustomed to release for the people any one prisoner whom they wanted. At that time they were holding a notorious prisoner, called Barabbas (v 15-16).

Matthew informs the reader that he is making an interjection by using the word now.

His expression at the feast refers to the Jewish celebration of the Passover and the feast of Unleavened Bread which was happening the very day of the trial. 

To learn more about Passover and the Feast of Unleavened Bread, see The Bible Says article "The Original Passover."

During the feast of Passover/Unleavened Bread, the Roman governor of Judea was accustomed to release for the Jewish people any one prisoner whom they wanted. 

Luke makes a similar remark testifying to this custom: "Now he was obliged to release to them at the feast one prisoner" (Luke 23:17). And Mark makes a similar interjection (Mark 15:6-7). John's gospel records Pilate as the one describing this custom (John 18:38).

After mentioning this tradition of Roman goodwill for the people of Judea at the Feast of Unleavened Bread, Matthew then mentions a key fact that was true at that time which played a major role in the final phase of Jesus's civil trial. 

This key fact was: At that time they were holding a notorious prisoner, called Barabbas.

The pronoun—they— in this statement refers to the Roman authorities. The Roman authorities were holding in their custody a notorious prisoner. Notorious means well-known and greatly disliked. Matthew does not explain why this prisoner was notorious or imprisoned—he only comments that he was. 

The other Gospels do mention this prisoner's notorious crimes. John says this notorious prisoner was "a robber" (John 18:40). Mark writes how this notorious prisoner "had been imprisoned with the insurrectionists who had committed murder in the insurrection" (Mark 15:7). And Luke comments: "He was one who had been thrown into prison for an insurrection made in the city, and for murder" (Luke 23:19). Taken all together, this prisoner was an insurrectionist who also committed murder and robbery and his crimes were well known to the people, and they greatly disliked him. 

Ironically, this notorious prisoner was guilty of insurrection—the same crime of which Jesus was accused (Luke 23:2) and declared to be innocent by both Pilate and Herod Antipas (Luke 23:14-15).

Matthew then tells us that this notorious prisoner was called Barabbas. 

It is unclear whether Barabbas was this prisoner's actual name, his nickname, or simply what the Gospel writers called and used to refer to him. 

The word, Barabbas, has Aramaic origins and it means "son of the father" (Bar = "son"; Abbas = "of the father"). There are two ways Barabbas's name and its meaning has been interpreted. 

The first way his name can be interpreted is as a kind of equivalent with Jesus. Jesus was the Son of the Father, so Barabbas literally has the same title as Jesus, "Son of the Father." The Gospel writers, and Matthew in particular with his Day of Atonement theme, seem to present Jesus and Barabbas as identical figures in terms of their humanity, even as they contrast them in terms of their righteousness. Jesus was innocent and perfectly righteous. Barabbas was a criminal, guilty of insurrection—the crime Jesus would be executed for. 

The second way Barabbas's name can be understood is as a kind of everyman. From Jewish records at the time, Barabbas was a common name. And even though it means "son of the father" it is ambiguous, because it does not specify who the father is of this son.

Every son is a son of some father, but the father's identity is undesignated in Barabbas's name, making him a figure that can symbolize every man. Moreover, Barabbas, the sinful criminal, and every man, has sinned and rebelled (committed insurrection) against God and His good authority. 

Thus, Barabbas is both a kind of identical figure equated with Jesus Christ; and as a criminal he is a representative everyman who is fallen and sinful.

Interestingly, church tradition suggests that Barabbas was only a title, and that this notorious prisoner's given name was "Jesus." Early church leaders, like Origen, claimed that Barabbas was named, "Jesus." Some late Greek manuscripts of Matthew 27:16 and 27:17 read: Ἰησοῦν Βαραββᾶν ("Jesus, Barabbas"). 

If this tradition is correct, the notorious prisoner and the Messiah each had the same name and the same title: "Jesus, son of the father." And if Pilate's two prisoners (the notorious insurrectionist and the Messiah) both shared the same name—"Jesus"—then it makes sense why Matthew wrote the prisoner was called Barabbas. It also gives further insight into Pilate's expression when he makes his offer to the people. The governor asks: "Whom do you want me to release for you? Barabbas, or Jesus who is called Christ?" (Matthew 27:17). 

In other words, Pilate may have been asking the people: "Which Jesus do you want me to release for you: Jesus, who is called Barabbas; or Jesus, who is called Messiah?" 

After inserting this important interjection—Now at the feast the governor was accustomed to release for the people any one prisoner whom they wanted. At that time they were holding a notorious prisoner, called Barabbas (v 15)—between the first and third phases of Jesus's civil trial, Matthew goes on to explain how these things played out between Pilate, the people, Jesus, and the prisoner called Barabbas (Matthew 27:17-26).