Matthew 27:3

‘Then Judas, who betrayed him, when he saw that he was condemned, repented himself, and brought back the thirty pieces of silver to the chief priests and elders,'

All that Matthew feels about Judas comes out here. ‘Judas who betrayed Him.' It says all that needs to be said. Then he describes Judas' actions following the betrayal. When he saw that Jesus was condemned he had a complete change of heart, and filled with regret and remorse he brought back the thirty pieces of silver to the Chief Priests and Elders. He wanted to transfer some of his guilt on to them, and possibly also in his naivete hoped to cancel the agreement. There may be a suggestion here that things had not turned out as Judas had expected. Possibly he had hoped that his actions would spur Jesus into Messianic action. On the other hand it may simply be that seeing Jesus condemned made him realise just what he had done.

‘Then -- when he saw.' Compare Matthew 2:17. It may be no coincidence that the same phrase introduces a connection with Jeremiah's prophecies in both instances, especially as both prophecies are also introduced with a unique parallel phrase, ‘then was fulfilled what was spoken by Jeremiah the prophet'. As we have seen there is good reason for seeing Matthew as using these prophecies as a framework in order to drawing attention to gloom and suffering, and attempts on Jesus' life, at both the beginning and the end of his Gospel. Judas is seen as having ‘achieved' what Herod had failed to ‘achieve', shedding the blood of Jesus, but only to his deep regret.