The most interesting Saints cover a broad spectrum. They transition from the generally bad state to sainthood state. Everyone likes the come from behind kid.
St. Augustine may have had the most sinful past. He fathered an illegitimate child. He eventually abandoned the child and the mother in the prospects of marrying a heiress. His mother, like almost all mothers, persisted that he repent. Eventually he did and turned to the priesthood. As a nod to his party past, he remains the patron saint of brewers. He apparently prayed for chastity, but not just not yet.
Ancient Rome subcontracted out tax collection to locals. These people were generally hated by all. Tax collectors notoriously extorted additional fees on top of the taxes. Even if they didn’t, they were seen as Roman collaborators.
Likely the most famous was St Matthew. Followers harangued Jesus for including roman collaborators. Eventually St. Matt moved out the money collection business and into Sainthood. I think it is telling that ever since tax collection in the US started, no one working there has been raised to sainthood.
St. Mary of Egypt lived in Alexandria in the fourth century. She was a ‘seductress’. Some research suggests she was a prostitute. Other studies suggest that St Mary never charged for her services. She seemingly liked the challenge.
Fortunately, she joined a pilgrimage to Jerusalem. She did this apparently to either drum up more business or join what would have been the closest thing to the mile high club. Either way she managed to seduce everyone along the way. When she finally got to the holy site, she saw a statute of the Virgin Mary and repented. What must be the greatest turnaround in ancient history, she is now the Patron Saint against sexual temptation.
St. Angela spent most of her life seeking wealth, material possessions and pleasure. As an aside, I really didn’t like where this one was heading. She had several children but was still more interested in gathering possessions.
At 40 she realized the emptiness of her life. Unfortunately, her mother, children and husband died three years later. She sold everything and joined an order and became the patron saint of widows. Part of her tagline includes adulteress. I am not sure what they did for SEOs back then.
The Blessed Bartolo Longo started off as a devout catholic. He may have been looking for more immediate gratification and became a Satanic Priest instead. He joined the Dominican tertiary and helped college students learn about the avoiding the evils of the occult. We can only be thankful that there was no cool aid back then.
All of these people focused on the long game. This means there is hope for all of us.