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5 Saints who were notorious sinners


Sharon Mollerus | CC BY 2.0

Philip Kosloski - published on 08/24/16 - updated on 09/21/23

These saints (a group that includes a former "loose woman," and a "low-life criminal") remind us that there's hope for us!

Saints, as we know, were not perfect. They made mistakes during their lifetime and often led public lives of depravity before their hearts were converted.

This is good news.

It gives us hope that even our cold hearts that are so distant from God can be turned towards him and given new life.

Saints always seem “too holy” for us to imitate, but really they were more like us than we realize. They struggled with the same addictions, pet sins and bad habits that we feel weighed down by today.

So let us take heart that these holy men and women were not always holy and through the grace of God overcame great obstacles to become shining examples of virtue. (For more great stories of saints who were sinners, check out Thomas Craughwell’s book, “Saints Behaving Badly: The Cutthroats, Crooks, Trollops, Con Men, and Devil-Worshippers Who Became Saints.”)

St. Matthew

No one has ever liked taxes and this was especially true in ancient Israel. During the first century Romans subcontracted out the job of collecting taxes to private individuals and these tax collectors took the opportunity to extort as much money as they could from people. Everyone hated them and their greed was well known by all.

That is why when Jesus asked Matthew to “follow him,” many were astonished and scandalized by the episode. How could Jesus dine with “tax-collectors and sinners”? Matthew was a changed man after that point, following Jesus closely and writing down everything in what we now call the “Gospel of Matthew.”

St. Dismas

Little is known about the “Good Thief” who was nailed on the cross next to Jesus, but we do know Dismas’ crime merited crucifixion. According to one biblical scholar, “Two of the most common [criminals condemned to crucifixion] were low-life criminals and enemies of the state… Low-life criminals would include, for example, slaves who had escaped from their masters and committed a crime. If caught, a slave could be crucified. There were two reasons they were subjected to such a tortuous, slow, and humiliating death. They were receiving the ‘ultimate’ punishment for their crime and, possibly more important, they were being used as a spectacle to warn any other slave who was thinking about escaping or committing crimes what could happen to *them*.”

At the last hour, Dismas understood the severity of his crimes and defended Jesus on the cross from the ridicule of the “bad thief,” “Have you no fear of God, for you are subject to the same condemnation. And indeed, we have been condemned justly, for the sentence we received corresponds to our crimes, but this man has done nothing criminal” (Luke 23:40-41). Jesus recognized the sincerity of his repentance and proclaimed, “Amen, I say to you, today you will be with me in Paradise.” After leading a life of sin, Dismas was granted pardon shortly before his death.

St. Augustine

Even though he was raised by a Christian mother, Saint Augustine followed the practice of many students of his time and pursued a life of pagan Manichaeism. During this time period he engaged in a relationship with a concubine and had a son with her. They remained with each other for many years, but he never married her and eventually she ended the relationship.

The best example that Augustine gives of the severity of his life of sin is the famous episode of the “stealing of the pears.” He narrates the scene in his Confessions.

Fair were those pears, but not them did my wretched soul desire; for I had store of better, and those I gathered, only that I might steal. For, when gathered, I flung them away, my only feast therein being my own sin, which I was pleased to enjoy. For if aught of those pears came within my mouth, what sweetened it was the sin.

After having a conversion of heart, Augustine was baptized, became a priest, bishop and after his death, “doctor of the Church.”

St. Pelagia

Pelagia was a well-known actress and “loose woman” in the fifth century. Saint John Chrysostom said of her, “Nothing was more vile than she was, when she was on the stage.” Craughwell paints the picture of her sins well, “The men she took as her lovers became intoxicated with her. For Pelagia’s sake fathers abandoned their children, wealthy men squandered their estates. She even seduced the empress’s brother. Trying to account for Pelagia’s power over men, St. John wondered if she drugged them, and speculated that perhaps she used sorcery.”

Not much is known about her conversion, except that she possibly heard a homily from a bishop about God’s mercy and then immediately asked to be instructed in the faith and then baptized. It is believed that she then became a nun and spent the rest of her days in prayer.

St. Mary of Egypt

At a young age Mary ran from home and spent seventeen years as a seductress in the glamorous city of Alexandria during the fourth century. She did not charge for her services, but enjoyed the challenge of seducing young men. She was enthralled with “sexual adventure” and was led by her passions. Mary later confessed, “There is no mentionable or unmentionable depravity of which I was not their teacher.”

Felling compelled to tag along with a group of pilgrims on their way to Jerusalem, she boarded the ship and seduced everyone before reaching their destination. However, while in the Holy City, Mary repented of her sins and was reconciled with the church.

She spent the rest of her life as a hermit in the desert and continually fought temptations to turn back to her depravity until God granted her peace of soul.

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