What does Matthew 26:14 mean?

Matthew often moves his telling of the events of Jesus life out of strict chronological order. This is a common tactic in ancient records: linking similar themes or moments together. Here, Matthew connects Judas' decision to betray Jesus with Jesus' defense of the woman who anointed him with extremely expensive ointment.

Assuming John 12:1–11 is describing the same event, it is Judas who asked why the perfume was not sold and the money given to the poor. Jesus insisted that the woman, Mary, was participating in the preparation of His body for burial.

Perhaps that was the breaking moment for Judas. He may have felt stung by Jesus' correction. He may have suspected Jesus knew he had been stealing money from the group's moneybag (John 12:6). Perhaps he recognized that Jesus was really, truly expecting to die and be buried. This would quash any hope for Jesus to be a military or political figure. Misguided hope that Jesus would defy Rome to usher in a new kingdom on earth was fading.

Whatever reasons Judas gave himself, Satan was involved in his decision to offer Jesus to the chief priests. The Devil put the idea in Judas' heart (John 13:2), Judas acted on it, and Satan entered him when the time came to act (John 13:27).