As we all know the books left a lot of questions unanswered. So many things are contradictory and just flat out don't make any sense.
I've often thought about Tom Riddle's time at Hogwarts and those memories that Dumbledore showed Harry. Many of the things Dumbles told Harry didn't make any sense. Worse some of the reasons he gave Harry for the things that he did make even less sense. I'm thinking here of Trelawney's interview being held in the Hog's Head because it was raining. Was she related to the Wicked Witch of the West? Did she fear death by melting? But I digress, back to my musings about Tom.
How was it that Tom was able to amass a loyal following that included the likes of Avery, Lestrange, and one can only assume Malfoy. Although they must have been the fathers of Lucius Malfoy's generation. I know Dumbledore tells Harry that he believed Tom did it by virtue of his Parslemouth ability, his charm, good looks, and superior intellect, but I have to wonder. Perhaps I'm too cynical, but during those "lessons" Dumbledore is so cagey in what he reveals I really have trouble taking anything he says at face value.
So here is my thought process, Tom starts Hogwarts in 1938 and he is sorted into Slytherin. The boy's origins at this point are a complete mystery. All that is known is that he was born and raised in a Muggle orphanage. With the great importance placed upon bloodlines and family ties, it is reasonable to assume that the child's parents were not magical. Having children out of wedlock would have been nearly unthinkable to the society stuck in the Victorian age. So as far as Riddle's housemates could see he was a muggle-born or at best a half-blood. Even him being a half-blood I think they would've discounted because again bloodline and family were so important. He could've been the product of a sexual assault but I think in their minds that would've been just as bad since he would've been a bastard.
What I picture is this muggle-born boy being sorted into the house that values blood purity over everything, he's there on a bursary/scholarship so he's penniless. He would have only second-hand robes and supplies, he would have known little to nothing about the wizarding world and its customs. We already know that Snape was not well treated within his house for being poor, it is possible that the difference was that Tom was attractive whereas Snape was not. I can see that Tom's housemates might have made his time there a living hell. I can even see that he might have felt that but for the ability to do magic he was no better off than at the orphanage.
So what about his Parselmouth abilities, could he have won his housemates over by displaying one of the traits of their founder? Possibly, but then again that might have made his situation worse. I think that the Slytherins would only have seen this jumped-up little "mudblood" having delusions far above his station and made it their mission to put him in his place.
I just don't buy that the Slytherins would have followed someone that as far as they knew was a "mudblood." Remember, Dumbledore tells Harry that Tom found out about his mother's family in the summer of his sixteenth year. Even if he found out much earlier about his family, I think the Slytherins would not have believed him or him trying to appropriate a status to which he had no right. I'm also not really sure about Tom's inclusion in the Slug Club unless it was for his brilliance alone. As a muggle-born or even a half-blood, Tom wouldn't have had much in the way of future potential to attract Sluggy's attention.
Dumbledore told Harry that he had considerable trouble locating anyone with memories of Tom's school days and those that did were reluctant to talk about it. But why would reluctance matter to a Master Legillimens? For that matter, why could Dumbledore not get the "true" memory off Slughorn?
In the alternate universe of my headcanon Dumbledore implanted those memories into Slughorn. The reason he couldn't find memories of Tom's time at Hogwarts is that everyone remembered Tom's school career very differently and what they remembered wouldn't fit the narrative Dumbledore wanted. In this alternate universe, Tom is treated as the muggle-born he appears to be and he resents the stuck up pure-bloods and vows revenge. He finds out he's descended from the Slytherin line but he keeps that information to himself. It is only after he leaves Hogwarts and vanishes for those ten years that he becomes Lord Voldemort. Then when he comes back to England no one except Dumbledore suspects that he's Tom Riddle. Voldemort avenges himself on Malfoy, Lestrange, Avery, and the rest by coopting the pure-blood dogma and enslaving their children. All the while taking great pleasure in seeing their sons and daughters groveling at his feet.
That sounds much more interesting to me than what we got. Tom was descended from rotten stock so that's why he's evil. Something for me to consider writing, maybe after I'm finished with my present fic.