The Geometry book [1] he wrote in high school is required reading for any serious competitor and I believe he is the main responsible for some bringing some techniques into the olympic meta, such as Barycentric Coordinates.
Also, his blog post [2] about writing is one of the best ones I've ever read.
[1] https://web.evanchen.cc/geombook.html [2] https://blog.evanchen.cc/2015/03/14/writing/
How about obscure stuff about hyperbolic trig functions (sinh, tanh and so on)?
An Infinitely Large Napkin - https://news.ycombinator.com/item?id=20168936 - June 2019 (32 comments)
An Infinitely Large Napkin [pdf] - https://news.ycombinator.com/item?id=12467506 - Sept 2016 (3 comments)