Tradition tells that during the Lord's earthly lifetime, his fame spread to Edessa, beyond the Euphrates River. While Jesus Christ was healing many among the multitudes in Israel, Prince Avgar of Edessa on the Euphrates was suffering with leprosy all over his body. He heard of the miracles Christ was working in Palestine.
Prince Avgar sent the court artist Ananius to Jerusalem, asking that Christ come and heal him of his leprosy. He instructed him that if the Master would not come that he was to paint His likeness for he believed that that would be enough to heal him.
The Lord's Passion was at hand, and he was unable to go to Prince Avgar Himself. Ananius tried his best to paint a portrait of Jesus, but was unable to capture his likeness. So Jesus took a napkin, and wiped his face with it, impressing his divine countenance on it, leaving a perfect image of His most pure face on it. He gave it to Ananias, sending it with a message back to Prince Avgar in Edessa. The message was that this napkin would heal him mostly, but that Jesus would send one of his disciples later to complete the healing. Avgar kissed the napkin and his leprosy left him, except for a small spot on his face.
Later, Apostle Thaddaeus came and preached the gospel to him. The prince was completely healed, and was baptized. The prince then smashed the idols at the city gates and placed the Holy Napkin above them, fastened to wood, with a gold frame and ornamented with pearls. He had inscribed above it: "O Christ our God, no-one who hopes in Thee will be put to shame."
Many miracles have been worked by this icon. In 944, during the reign of Emperor Constantine Porphyrogenitos, the image was moved to Constantinople, and a feast was established in its honor on 16 August. It remained there until the Turks destroyed it in the 15th century. Some say it was lost at sea during one of Byzantium's battles with the Huns.