Judas Iscariot was the most infamous traitor the world has ever known.
His plan was to betray the Lord with a “kiss” (phileo: to show brotherly affection; a warm greeting — Mt. 26.48). Instead, when he arrived, Judas “tenderly-kissed” him (kataphileo—v. 49). This was no standard peck on the cheek.
The intensive form denotes a display of both passion and fervent tenderness. It may suggest a lingering show of affection (as a mother to her child), or a repeated greeting, to display respect. The irony of this “sign of betrayal” — not lost on anyone — is only augmented by this insight.
But Judas’ verbal greeting to the Savior is likewise brimming with irony, and equally twisted in import. “Hail, master!” was his cry.
First, there is the obvious use of, master (rabbi), which literally meant, my great one, or, my honorable sir — this from the one who was to hurl the Lord headlong into bitter shame and reproach (cf. Heb. 12.2; Mt. 27.28-31, 39-44).
Second, and perhaps more devious, the word, “Hail” (chairo), conveys both joy and grace: “Rejoice! Be gladdened by favor!” Set that in contrast to the Lord’s sleepless night of sorrow and distress, owing to the death set before him, spearheaded by this very same renegade (Mt. 26.37-38).
Duplicitous does not even begin to describe this man’s twisted treachery!