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

Principal Winston is the principal of Westchester Country Day. He was introduced in Tales From a Not-So-Popular Party Girl.

History[]

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 tried to call Nikki's father because of a bug problem at school, but Nikki was trying to prevent it, in order to not be revealed that she is in WCD because of a bug extermination scholarship. However he meets Nikki's parents in a restaurant. Furthermore he congratulated Nikki for her participation in WCD Talent Showcase.

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 bad. 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-Smart Miss Know-It-All[]

MacKenzie comes to his office alongside with Nikki, Chloe and Zoey, as she threatened to report them to Principal Winston for toilet papering her house and (false claim) throwing eggs at it. But Marcy comes in and asks MacKenzie for an interview about locking Nikki and her friends inside a storage room during The Holiday on Ice show. MacKenzie got surprised and then Principal Winston came in, asking MacKenzie the reason she called him. Instead of telling her reason, in fear of getting exposed, she makes up a fake reason, that she wanted to add more apple meals in school cafeteria. So that meeting ended.

Tales From a Not-So-Happy Heartbreaker[]

Principal Winston is the person who announces the Sweetheart Princess.

Tales from a Not-So-Dorky Drama Queen[]

Principal Winston stares at Nikki, Chloe, and Zoey.

Tales from a Not-So-Perfect Pet Sitter[]

Nikki and her friends left Holly and her puppies in principal Winston's office, because they knew that he would not be there all day, as he had a visit in WCD High School. However he returned and saw the puppies out of their cage. As a result he became angry and threatened to call Nikki's parents (and the rest of her friends'). But Max Crumbly came in and had a conversation with him and took the puppies. So, nobody got trouble.

Personality[]

Nikki describes him as a little odd, but, after working at a middle school for many years, she doesn't blame him. However it is hinted that he is strict and punishes a lot, because Nikki is afraid of him, and doesn't tell him anything bad happens to her (For example in book 9)

Appearance[]

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.

Trivia[]

  • It is hinted that he is afraid of dogs, because he called Holly and her puppies "wild dogs", despite the fact they are golden retrievers.
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