...and that is why I hate school!
Chester concluding his speech in A Wonderful Thanksgiving.

General Information
Gender: Male
Age: 8 (season 1)
9 (season 4)
10 (season 3)
Hair Color: Blonde
Eye Color: Brown
Birthday: c. 2003
Address: Chicago, Illinois (2003-2013)
Occupation(s): Student
Series Information
First appearance: The Punishment You Get
Last appearance: Number Two on Your Shoe (physical appearance)
The Road...Here We Come (mentioned)
Portrayed By: Buddy Handleson

Chester is a recurring character in the fictional series BABYSITTER. He was a former student at Chicago All School. He made his first appearance in The Punishment You Get, when Madison and Babushka were handing out broaches to some of the nearby students. It was revealed that he was harboring a massive crush on Babushka ever since she came to the school. Through-out the series, he always wanted to impress Babushka and ask her out, however Babushka thought he was annoying and often rejected him. Babushka grew feelings for Chester in A Wonderful Thanksgiving after listening to him deliver a speech about how much he hates school. Although she regretting going to the Thanksgiving Dance with him, the two of them were revealed to be dating (through-out most of season 3; although none of their relationship was shown on-screen [with the exception of Number Two on Your Shoe]). However, in The Road...Here We Come, Babushka told Madison that her and Chester broke-up and he changed his name to Wendell and moved in with Vinnie.

He is portrayed by Buddy Handleson.