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Herbert first appeared as a freshman who was assigned to Steve Sanders as his "senior buddy". Herbert was a computer nerd who Steve regarded as a pest more than anything.
However, when Steve was assigned the Legacy Key, he needed someone who knew computers to help him change some grades in his computer. He talked Herbert into breaking into the school with him and they changed Steve's grades.
However, when an investigation occurred on the break-in, Steve begged Herbert to take full credit because he would get a lighter sentence. Herbert refused, told Steve off, and went on with his life. Ashamed of his actions, Steve turned himself in and took full credit for the break-in, leaving Herbert's name out of it.