This came up in a discussion with an old friend recently, and I realized I should share it on here.
It was towards the end of my senior year of high school in March 1999.
A little backstory: My school required all freshman to take a class called "Skills for Success", basically a class about how to apply for a job, how to manage a checking account, and etc. there was only one teacher for this, we'll call him Mr. X. He was nearing retirement (I think he retired around 4 years after I graduated) and he was the only teacher to teach this class, and thus, it was his only class he taught. He also was quite "liberal" in the classroom, and would throw out plenty of curses if need be....generally the type of teacher I liked. I also came to realize he was a big sports junkie, like myself, so we began to frequently talk about sports. Even after my class with him my freshman year, I would frequently pop-in at the end of the day (throughout the rest of my years in HS) to chat for 10-15 minutes about what was happening in the world of sports before leaving to meet up with friends and whatnot.
Now forward to March of '99. We were chatting outside my locker one afternoon about the upcoming March Madness tourney. Mr. X proceeds to tell me that the teachers ran a kinda-for-fun pool for the brackets. $1 buy-in. He said that if I wanted in, to fill out a bracket and he would submit in under his wifes name. Of course I was in. The tourney starts and I'm hitting pretty well on a lot of early round games, but nothing spectacular. But then, around the sweet sixteen, I am killing it. I wind up picking the final 4 teams exactly right. Mr. X catches me at school the Monday after the Elite 8 games were done and told me I had already won the pool! He also told me that another teacher, Mr. S, was the one in charge of the pool, and that he told him that it wasn't really his wife, but my entry. Mr. S i also had become somewhat familiar with throughout high school, and at the time, I had a computer class in his lab where his office was. the next day I come into the class, and he pulls me aside while walking in and asks me to step into the hallway with him. Mr. S then proceeds to palm me the $55 I won with a simple question (with a smirk on his face); "How in the fuck did you get all 4 final teams exactly right?"
I still haven't met anyone else in life who won their teachers March Madness pool as a high school student.