Matthew 27:26 meaning

The parallel gospel accounts of this event are found in Mark 15:15, Luke 23:24-25 and John 19:13-16.

After multiple proclamations that Jesus was innocent, and many failed attempts to release Him, Pilate caved to the relentless hatred of the crowd and violated his conscience. 

Matthew gives a brief and summary of the three major outcomes of Jesus's civil trial:

Then he released Barabbas for them; but after having Jesus scourged, he handed Him over to be crucified (v 26).

From the other Gospel accounts, especially John's, it appears that these outcomes were not all delivered at once or at the trial's conclusion. But rather they seem to have been delivered over the course of the third and final phase of Jesus's civil trial. 

Matthew's summary of these outcomes concludes his portion of how Jesus was unjustly treated under Pilate. Matthew's next section describes how Jesus was unjustly treated by the Roman soldiers (Matthew 27:27-30). 

The first outcome Matthew summarized is: Then Pilate released Barabbas for them.

Pilate's release of Barabbas came after the governor offered to release Jesus as part his customary "Passover Pardon" (Mark 15:9, John 18:39). This was Pilate's second attempt to release Jesus. But instead of accepting his offer, the Jews appeared to make a counteroffer and demanded that Pilate release the notorious criminal Barabbas instead (Luke 27:18; John 18:40). After some additional back and forth, Pilate released Barabbas for them.

The second outcome Matthew summarized was mentioning that Jesus was scourged.

Luke and John tell us that Pilate had Jesus scourged as part of another attempt (third) to release Jesus (Luke 23:22, John 19:1-5). 

Matthew records that Pilate handed Jesus over to be crucified after he scourged Him. This indicates that Pilate scourged Jesus before he decided to hand Him over for crucifixion as Luke and John's more detailed accounts on this point also describe. As Pilate's third attempt to release Jesus, it seems he was hoping to show the crowd a brutalized Jesus, which would cause them to relent. Instead, it appears to have propelled their blood lust. 

Matthew's summary of the trial's three outcomes does not appear to suggest that Pilate scourged Him after he handed Him over to be crucified or that he scourged Jesus twice. 

Scourging was a brutal and bloody form of punishment. The next section of The Bible Says commentary (Matthew 27:27-30) explains Matthew's account of how the Roman soldiers abused and mocked Jesus, and it describes what it meant to be scourged.

The third outcome Matthew summarized was the most important: he handed Him over to be crucified.

Jesus had been sentenced to death by Roman crucifixion. 

Roman crucifixion entailed fastening its victims to a upturned wooden beam by the wrists (often with nails) to hang there until death. Archeological evidence also shows that the ankles were sometimes nailed, not together on the front of the cross, but individually on either side of its main beam. Crucifixions were carried out in public places with the crimes of the crucified posted for all to see as a way to be deter future crime. Criminals would sometimes agonize on their crosses for multiple days before they perished from suffocation, dehydration, or cardiac arrest. The entire process was designed to be brutal and humiliating and serve as a deterrent for breaking Roman law. 

And so, after many fiendish twists and unexpected turns, the religious leaders' conspiracy to murder Jesus had achieved its goal. What was put in motion when Judas informed the priests that Jesus had identified him as part of the plot twelve hours earlier, appears to have led to their scrambling to arrest Him; secretly and unlawfully gather for nighttime trials; flail to find a charge; stage a "crime" to condemn Him for; retry Him at sunrise; bring Him before Pilate; follow Him to Herod's court; and relentlessly pressure Pilate to crucify Him—had resulted in the verdict and outcome they sought. Jesus would die so that the priests and elders could keep their position within the nation (John 11:49-50).

Pilate had wanted to release Jesus. He had even decided to release Him (Acts 3:13b). But Jesus was disowned by His own people who asked for a murderer to be granted freedom instead of the Holy and Righteous Messiah (Acts 3:13b-14).

Mark reveals that the reason Pilate handed Jesus over to be crucified was because he was "wishing to satisfy the crowd" and avoid a riot (Mark 15:15). In particular, Pilate was boxed into a corner by the Jewish leaders assertion that "We have no king but Caesar" (John 19:15). This framed Pilate's decision as "If you crucify Jesus you are loyal to Caesar, and if you let Him go you are not."

Luke writes of Pilate's fateful decision:

"But [the people] were insistent, with loud voices asking that He be crucified. And their voices began to prevail. And Pilate pronounced sentence that their demand be granted. And he released the man they were asking for who had been thrown into prison for insurrection and murder, but he delivered Jesus to their will."
(Luke 23:23-25)

John is more succinct: "So he then handed Him over to them to be crucified" (John 19:16).

Nothing about this outcome shocked Jesus. He had predicted He would be handed over and crucified (Matthew 20:18-19). None of this took God by surprise. God foreknew, even before the world was made that this would happen (Revelation 13:8). God predicted this when Adam and Eve sinned for the first time (Genesis 3:15). God sent His Son to die for the sins of the entire world (John 3:16). Isaiah makes it amply clear that it was the LORD's plan, will, and desire that Jesus be killed:

"But the LORD was pleased
To crush Him"
(Isaiah 53:10) 

"The things which God announced beforehand by the mouth of all the prophets, that His Christ would suffer, He has thus fulfilled."
(Acts 3:18)

With Pilate's handing Him over to be crucified, Jesus's civil trial had concluded. After narrating the judicial proceedings of Jesus's trial under Pilate, Matthew then narrates how Jesus was mocked and abused by the Roman soldiers in the next section of scripture (Matthew 27:27-30).

To learn more about the timing and sequencing of these events, see The Bible Says' "Timeline: Jesus's Final 24 Hours."