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Margaret Olmstead is the main antagonist and villain alongside Chucky Barnes in Journey Birthday Boy. She is voiced by herself. She is friends with Chucky Barnes and enemies with Harry D. Rabbit and his friends.

Margaret is the first female villain of Harry and Friends. She was first seen walking along the same wharf in Louisa Street Wharf where Earl was skateboarding. She was pushed in the water by Harry and drowning to death after she, Chucky and his pet snake Angriness kidnapped the Journey singer Steve Perry's girlfriend Sherrie Swafford, Stinky Jones's girlfriend Wendy Wong and Harry's teacher Mr. Conrad. Margaret Olmstead was buried to her funeral the next day (Earl's 8th Journey birthday party and Harry's great-grandpa's funeral). She is no longer a villain or bully after being pushed by Harry and drowns to her death after Journey Birthday Boy.

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