Simeon was Syrian and, when he was 30 years old, he entered the monastery of Abba Gerasimus in Syria. He then spent the next 29 years in a desert near the Dead Sea. He was then directed by God to move to Emesa for help the poor of that city. He asked for the grace to not be acknowledged for his help. He came to learn that the best way to be humble was to love humiliation so he took it upon himself to act foolishly. Only the truly wise could see Simeon's sanctity.
By simulating madness, he saved many souls and brought them to Christ. He was also able to heal many possessed people by his prayer, fed the hungry, preached the Gospel, and helped needy citizens of the town. Most of Simeon's good deeds were done secretly.
Simeon didn't play a fool with his friend John, deacon of the church in Emesa. Simeon once saved John from being executed when he was falsely accused. Shortly before his death, Simeon told John:
I beg you, never disregard a single soul, especially when it happens to be a monk or a beggar. For your charity knows that his place is among the beggars, especially among the blind, people made as pure as the sun through their patience and distress...[S]how love of your neighbor through almsgiving. For this virtue, above all, will help us on [the Day of Judgment.]
Simeon died in AD 570 and was buried by the city's poor in a potter's field. While the saint's body was carried there, people heard a choir singing though none could be found anywhere.
He is traditionally shown holding a puppet which he used to mock himself and to ridicule the sins and foolishness of others. Very much like how modern ventriloquists use their dummies.
His hagiographers explain that God blessed Simeon with extraordinary happiness. He was the first saint to be venerated explicitly as a "fool for Christ's sake."
There are many people who think Christians to be foolish. St. Francis reminds us:
Let us pay attention, all my brothers, to what the Lord says: "Love your enemies and do good to those who hate you," for our Lord Jesus Christ, Whose footprints we must follow (cf. 1Pt 2:21), called His betrayer "friend" (Mt 26:50) and gave Himself willingly to those who crucified Him. Our friends, then, are all those who unjustly afflict upon us trials and ordeals, shame and injuries, sorrows and torments, martyrdom and death. We must love them greatly for we will possess eternal life because of what they bring upon us. - St. Francis of Assisi. Earlier Rule, §22. Classics of Western Spirituality.
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