On March 11, 2020, The World Health Organization (WHO) declared the COVID-19 pandemic status (WHO, 2020). There is no doubt that teachers endured higher stress levels because of new expectations and anxiety. In the face of myriad challenges, teachers did their best but needed acknowledgment of that fact from their principals. Did teachers trust that their principals understood and provided what they needed most to succeed during these unprecedented times? The purpose of this study was twofold. First, to determine if there was a relationship between the principal's use of Charismatic III: Self Sacrifice and teacher job satisfaction with the supervisor when controlling for working conditions during COVID-19, availability of safeguards, and risks due to expectations. The second was to determine if there was a relationship between working conditions during COVID-19, availability of safeguards and risks due to expectations, and the principal's use of Charismatic III: Self Sacrifice. Convenience sampling with 186 participants contributed to this non-experimental study. Data was analyzed using descriptive statistics, Pearson correlation coefficient, and multiple regression. Betas and Partial correlations were further analyzed for continuous variables. The results showed that working conditions were the strongest predictor amongst the other variables, consisting of the availability of safeguards, risks due to expectations, and the principal's use of self-sacrificial leadership. This study provided significant evidence that working conditions do have an impact on teacher job satisfaction; working conditions explained 68% of the variance in Teacher Job Satisfaction with the Supervisor. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]