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Herman was arrested and imprisoned at Seagate Prison, coinciding in the prison with Trevor Slattery. Herman began to idolize Slattery for his criminal history like many other immates, and he became the unofficial butler and aide to Slattery. He was in charge of simple tasks, such as getting Slattery his lunch. He also acted as a bodyguard, and would protect Slattery from anyone who threatened him.
One day during lunch, Slattery accidentally spilled his tray on another inmate known as White Power Dave. Dave began threatening him, so Herman and another group of inmates led by Fletcher Heggs came to Slattery's side. Realizing he was outmatched, Dave backed down.