The Saint Louis Tribune was not alone in casting doubt as to whether Dorothy Day could become a saint: They asked, "Could a bohemian journalist, who had a failed marriage and an abortion, be a candidate for Catholic canonization?" 

This, it seems to me, is a bit of a strange question because in reality aren't all saints unlikely?

I did a little research and came up with a few saints that jumped out at me as some of the most unlikely.

1) Moses the Black - Besides having one of the coolest and most ominous sounding names in the history of Christianity his story has to be one of the unlikeliest saint stories.

Moses the Black (I just love saying his name) was a slave of a government official in Egypt who fired him for pure badassery. Think about that for a second. Dude was so bad he got fired from being a slave. Internalize that for a moment, would you? Turns out that his owner suspected him of nothing short of thievery and murder. And knowing that he himself was human and was required to close his eyes for 6-8 hours a night and Moses probably didn't have any such weakness like sleeping, he thought it best to simply fire him. Politely.

But it doesn't end there. Moses the Black quickly joined a gang of bandits and was almost immediately made their leader and probably not just because he had the most awesome name. Catholic.org recounts a story that would make Chuck Norris uneasy and PETA would most assuredly file lawsuits:  
On one occasion, a barking sheep dog prevented Moses from executing a planned robbery, so he swore vengeance on the owner. Carrying out his threat, he approached the hut of his victim from the opposite side of the Nile and, placing his weapons between his teeth, swam the river. The owner of the dog heard the approach, so he hid along the river bank, thus escaping disaster, Moses, not finding the shepherd, took four rams from the flock, towed them back across the river, flayed them, sold the skins for wine, cooked the best parts, and feasted before walking back 50 miles to his camp.  

When the law seemed to be catching up with Moses the Black for assorted mayhem he decided to hide from the authorities in a monastery in the desert. And that's where MtB found Christ. So then, Moses the Black became a humble servant of God, right? He did experience a true conversion but he was still Moses the freakin' Black. Proving that you can be both Catholic and hardcore, Moses performed one of the most amazing conversion stories 

Four of the stupidest robbers in the world decided to rob the monastery where Moses lived. This is one of the stupidest decisions in the history of the world for two reasons:

1) Monasteries are typically the poorest places in the world.
2) Moses the Black was living there.

Moses completely overpowered them, tied them up and dragged them to the chapel. He announced that he didn't think it would be Christian to beat them into gruel which so moved the robbers that they reportedly repented and became monks as well.

He was later martyred as an old priest, allowing himself to be martyred by bandits after sending many of the other monks away.

2) Wilgefortis and her Dad didn't get along all that well. While the acrimony likely stemmed from her father actually naming her Wilgerfortis, it only got worse when her father promised the Catholic teen to a pagan king.

Wilgerfortis, however, had taken a vow of virginity so she did what every teenager with a vow of virginity who had been promised to a pagan king does. She prayed that God would make her unattractive to the pagan king. Well, we all know that God sometimes answers prayers in funny ways but this one takes the cake.

In answer to her prayers she sprouted a beard, which pretty much ended the engagement. For this, her father crucified her which is also an effective (and permanent) way to ensure you're not reluctantly married to a pagan king.

3) We are all guilty of piercing our Lord and Savior in some sense. But only one saint actually pierced the side of our Lord and Savior. St. Longinus is the centurion who pierced the side of Our Lord while He was hanging on the Cross. That's a pretty bad moment in life when you put a spear into God. You'd think some pretty nasty eternal comeuppance would be coming his way.

But no.

Longinus, who reportedly had some bad peepers, was healed when some of the blood and water from Jesus fell into his eyes. It was then he exclaimed "Indeed, this was the Son of God!"

Longinus then converted, went AWOL from his gig as a centurion, took instruction from the apostles, and became a monk.

He was later arrested for the crime of being a Christian. They pulled out his teeth and cut out his tongue. (Hey, but his eyes were still 20/20.) But none of that stopped Longinus who miraculously continued to speak and destroy several idols in the presence of the governor. The governor immediately went blind only to have his sight restored when St. Longinus blood sprayed all over him when he was beheaded. (How awesome is that?)

And while becoming a saint is pretty much the bomb, you know Longinus must have thought it was pretty awesome when he was portrayed by John Wayne in The Greatest Ever Story Told.

You know Pope Julius II brags sometimes about Rex Harrison played him in the movies but Longinus totally has the trump card. "John Wayne played me." Yeah, that probably keeps everyone quiet.