! This article contains spoilers. Read at your own risk!  !

Principal Winston is the principal of Westchester Country Day middle school. He was introduced in Tales From a Not-So-Popular Party Girl and drawn in Tales From a Not-So-Talented Pop Star.


Tales From a Not-So-Popular Party Girl

Principal Winston helped Nikki and the rest of the dance committee throw a Halloween dance for the school. At first he thought he was being prank called because it was only about 6:00 A.M. when Nikki explained everything to him and apologized for waking him up, he gave her permission to continue the dance.

Tales From a Not-So-Talented Pop Star 

In this book, Principal Winston calls Nikki's father because of a bug problem at school.

How to Dork Your Diary

Principal Winston walks in while MacKenzie Hollister is threatening Nikki. She stops in her tracks because she doesn't want him to know that she's evil. He asks what's going on and MacKenzie makes up a fake story and about the whole thing. Even though Nikki did wrongly accuse her, the whole fake crying 'thing' made her look worse.

Tales From a Not-So-Happy Heartbreaker

Principal Winston is the person who announces the Sweetheart Princess


Nikki describes him as a little odd, but, after working at a middle school for many years, she doesn't blame him.


Winston is an elderly man who has a mustache that is connected to his beard which are believed to be white. He wears suits when he goes to work at school and has glasses.