Great and Holy Wednesday: Betrayal and Repentance

On Holy Wednesday, the Orthodox Church draws our attention to two contrasting figures from the Passion narrative: the sinful woman who anointed Jesus, and Judas Iscariot who betrayed Him. The repentant woman acknowledged Christ as Lord and found forgiveness, while Judas turned away from the Master and became enslaved by sin​.

The repentance of the sinful harlot is thus contrasted with the tragic fall of the chosen disciple. According to the hymns of this day, Judas perished not simply because he betrayed his Master, but because after falling into sin he despaired and refused to seek forgiveness​. We do not recall Judas’ failure with self-righteousness, but rather with humility, recognizing that we too have often betrayed the Savior through our sins.

The Church therefore invites us on this day to sincere repentance, learning from the harlot’s example and avoiding Judas’s tragic path of greed and despair. (In many Orthodox communities, the Sacrament of Holy Unction is also served on Holy Wednesday evening, emphasizing Christ’s healing mercy and the forgiveness of sins​.)

Gospel Reading (Matthew 26:6–16)

In this passage, we read that while Jesus was in Bethany at the house of Simon the Leper, a woman came to Him with an alabaster flask of very costly ointment and poured it on His head as He sat at table.

Jesus praised her act of devotion, saying she had anointed Him for His burial, and that her deed would be remembered wherever the Gospel is preached. In stark contrast, Judas Iscariot went to the chief priests and agreed to betray Jesus in exchange for thirty pieces of silver​.The juxtaposition of these two responses to Christ provides a powerful lesson.

In the Gospel narrative we thus see two paths: one of repentance leading to mercy, and one of treachery leading to destruction. The Church urges us to choose the path of repentance, identifying with the humble myrrh-bearing woman rather than with Judas. Like her, we are called to pour out our love and contrition at Jesus’ feet, trusting that no sin is so dark that Christ’s forgiveness cannot overcome it.

Hymns of Holy Wednesday

The liturgical poetry of Holy Wednesday (sung at the Bridegroom Matins service on Tuesday evening) further illuminates these themes. This beautiful penitential hymn – chanted only once a year and considered a musical high point of Holy Week​– gives voice to the repentant woman’s heart. In it, the sinful woman speaks directly to Christ, expressing her sorrow and hope. The hymn opens with her lament:

A Prayer of reflection and Repentance

O Lord Jesus Christ, on this holy day of Your Passion we remember the repentant woman who bathed Your feet with her tears, and we remember the betrayal by Your disciple. You received the humble sinner and forgave her many sins, while the proud disciple fell away and perished in despair.

Grant us the grace of true repentance. Cleanse the darkness of our hearts with the healing oil of Your mercy. Do not let us ever be overcome by greed, pride, or unbelief as Judas was, but draw us to turn back to You whenever we fall.

Lord, like the sinful woman, we bow before You: forgive our sins and fill us with Your light. Help us to offer You the worship of our love and to remain faithful to You all the days of our life, for You are holy and compassionate, now and ever and unto ages of ages.

Amen.