A society depends a lot on the capability of our leaders. Being a leader means setting an example for others and how well you are at your job. People look forward to a leader for guidance and direction. Leadership qualities are all about your character traits and competence. Things can become drastic and tragic when the leadership totally fails and the leader fails to lead. This essay is a case study of failed leadership and its results based on analysis done by Tom Karen’s darker sides of Blue (Anthony T. Kern, 1995). There are three objectives of this case study: firstly, integrating the elements into the story for perfect case studies. Secondly, analyze leadership qualities and identify possible causes for the failures and learning lessons from it. Finally, besides the failures demonstrate the positive side of timely and proactive manner in this case study. However, the essay does not intend to pass on blames to the individuals instead the purpose is to study the potential significant errors in the leadership irrespective of the rules and regulations.