I hope someone can help me! I’m trying to remember the title of a book I read a few years ago. It’s set in a boys’ boarding school. There’s a big award for the best essay, and one teacher is the judge. He narrows it down to two, and then struggles to declare the winner. The teacher decides to name the slightly weaker essay the winner in an effort to give that student a boost. The teacher thought the boy who really should have won had enough other good things going on in his life that it wouldn’t make much difference to him. However, it’s devastating to him. And the boy who does win is not as deserving as the teacher thinks.
I know this is a vague description. I hope it’s enough to jog someone’s memory!
I love literary mysteries like this.
I wish I did know the title! I would read it.

I did re-read the Chatham School Affair last night…a good boarding school novel…
Ooo, that sounds like my type of book! I want to read it too!
Was it Old School by Tobias Wolff?
I could be totally off here, but… Wasn’t Old School about a young man who stole a girlfriend’s story and won a prize for it at his boarding school?
Back in 2002-3, I saw the movie titled The Emperor’s Club with Kevin Kline, exactly like OP described.
Thanks! The Emperor’s Club sounds right, but I don’t remember seeing the movie. The book it’s based on (a short story, actually) is in my library and I’ve requested it–The Palace Thief by Ethan Canin. I did read Old School, too. Maybe I’m mixing the two of them up? Good to know about the forum on Goodreads, too.