This chapter presents a complex, real-life, accessible case study in expecting the best to provoke and stimulate conversation around practical problems and alternative solutions that confront educational leaders today. It presents a case of a teacher engaging in unethical, immoral and unlawful behavior with a special needs student. The teacher was presented with a written reprimand that detailed her behavior towards the student along with the child's Individual Education Plans (IEP), a legal document that must be followed to the letter of the law. The teacher was continuously observed and her actions were documented. After sufficient documentation was collected, the teacher was asked to tender her resignation. The school administration supported the decision of Charlie Miller asking the teacher to resign. Miller's immediate supervisor formulated a policy based on this experience that is known as the Charlie Miller rule.