Chapter Text
Dean Winchester became legendary his very first night at Hogwarts. Oh not Harry Potter legendary, rather more of a fun fact legendary. The fun fact is this - that in the history of the school, he was the person it took the longest to sort. It took so long in fact that they started the banquet while he just sat there (they had lucked out that he had been the last child to be sorted anyways). Two hours later the hat finally, tiredly, yelled "Hufflepuff." At that point everyone was full and a little bored so there was less cheering than there might have been otherwise.
It was joked about for the first couple of months. Light teasing from some, derision from others, but generally Dean was an affable sort and paid it no mind. It died down and in that first year, Dean did nothing to distinguish himself. Some fellow Hufflepuffs asked why the sorting hat had put him in that house and Dean just shrugged it off.
The next year and the start of the sorting, Headmaster McGonagall made a comment about hoping that the sorting went easier for the new students than it did for Mr. Winchester. There was good natured chuckling, and Dean gave a wave. A couple of the new kids asked him about it, but he brushed off the questions easily. He made the quidditch team as a chaser, and was fair but not remarkable. He was quiet in class, but his teacher's realized that he was quite smart and performing excellently. He had a small but tight circle of friends, fellow Hufflepuffs Castiel and Garth, Ravenclaw Charlie, Gryffindor Ash, even Slytherin Meg (though that was mainly by accident). All in all, another year passed with Dean not really being noticed beyond any other student really.
It was in third year though that things began to change. He became head chaser and scored more than any other chaser in the last 25 years, 40 for a Hufflepuff. Students didn't notice his class marks, but his teachers knew that some of his grades could rival any in Ravenclaw, and put a puzzle in front of him, and he could solve faster than anyone else. There were again the jokes about sorting, but people were starting to grow more curious. Some of his friends asked why he was sorted into Hufflepuff, but he just wouldn't answer. People were beginning to notice Dean.
In his fourth year it all really changed. A few people had asked their younger siblings to ask the sorting hat about Dean, but the response was always the same, "a tough case, but I always set you right. Now don't worry about him, let's get you sorted tight." This only encouraged the rumours and questions. It really grew to a head one winter's day that year on the trip to Hogsmeade. Some older Slytherins were bullying young Griffyndor Krissy Chambers. Dean didn't know her, but he hated cruelty. He without thinking stepped in front of her and faced down the sixth year guys. They tried to taunt him, but Dean just stood in front of her, and protected her. They tried to sneak a hexing curse at Dean, but he responded in the way his stepfather Bobby taught him, a vicious right hook, followed by a knee to the stomach and a swift kidney punch. Rumours quickly spread about his bravery and courage and people began to say that he should have been a Griffyndor. Dean laughed and tried to play down the situation, but Krissy wouldn't let him.
Now George Weasley had never been one to miss an opportunity and had opened a satellite shop in Hogsmeade, which did a booming business. If you knew the right person, and asked at the right time, there was a betting book you could take part in. Ever curious George had placed a bounty - 2 Galleons to whomever could find out why Dean Winchester was sorted into Hufflepuff.
In Dean's fifth year, Sam came to Hogwarts. No one cheered so loud as Dean when Sam was sorted into Ravenclaw. With Sam there, everyone was sure that they'd find out the mystery of Dean's sort, but Sam explained (over and over and over) that he had never asked, because Dean seemed happy as a Hufflepuff and if he wanted people to know, then he would have told them. The bounty on the books went up to 4 Galleons.
Dean started to date a fellow Hufflepuff named Lisa. It lasted 3 months, but no matter what she tried, she couldn't get the answer out of him, and in frustration she dumped him and moved on to another guy. Dean seemed a little sad, but his friends always cheered him up.
The bigger problem was in that 3 months a third year Slytherin named Ruby had befriended Sam. It had worried Dean a little, she was known for playing some nasty pranks, but Sam was happy so he let it go. That is, he let it go, until Ruby pranked Sam with a potion that landed him in the hospital for three weeks. It took Dean months to plot out her downfall, he refused to let anyone help him, though they offered. No one was sure how he got into the Slytherin girl's dorms (Meg had a proven alibi), no one could even prove that it was him. All they knew was that Ruby now jumped at every little sound, shook whenever thunder clapped and her nerves were so frayed that her family pulled her out of school for a stay at St. Mungo's. At this, everyone began to say that maybe Dean should have been a Slytherin - it was cold, ambitious and ruthless. The bounty on the betting books went up to 10 Galleons.
Dean was embarrassed to start his sixth year as the paper had run a small article about Hogwart's O.W.L.s from the year before and Dean had the third highest marks in his year. The article even had a quotation from the Defense Against the Dark Arts professor, Gabriel Novak (Castiel's older brother), about how it was the fastest anyone had completed the Honourary Lupin Obstacle Course. Now the student body knew what the teacher's had - that Dean had been smart enough to be in Ravenclaw. Bobby and Ellen had been so proud of him that they bought him a new broom, as he had also been made Captain of the Hufflepuff Quidditch team. Dean knew that that article would just increase the people bugging him at school about why he was a Hufflepuff. He knew about the bounty held at Weasley's, wondered what it was up to. He was determined that no one during his last two years of school was going to win that money.
After the article came out the bounty was up to 20 Galleons.
Benny Lafitte was the Griffyndor Keeper. He was also in year 6. He was broke. He was broke and needed a new broom. He was going to win that bounty.