In times of a troubled situation in the business world, any organization may experience unwanted situations due to several reasons such as internal and external factors; management issue, culture differences, internal and external bias in decisions, and economic crisis, oil price fluctuations, financial downturn, political and regulatory matters, terrorism, disruptive innovations, and consumer behaviors. These would have various negative impacts on the organization, employees, and society as a whole. The result could be devastating sometimes. The foremost burden falls on the shoulders of the leaders who are leading these companies, and their course of action whatsoever will be forced to deal with sudden complex tasks and changes to tackle such challenges. Therefore, it is very crucial to have an effective leader to ensure the stability of the business and for sustainability in the long run. Easier said than done, many companies in such scenario cannot resist the difficulties, and most of the time, some might be saved by some charismatic leaders while some have no option than to collapse. Thomas Cook Group, in 2019 came across such a similar situation and strived to survive the 178-year –old travel company but eventually failed. Thus, the purpose of this paper is to discuss the situation of Thomas Cook and the role of different leaders in times of their turbulence. It is also an opportunity for students to examine the differences of actions required by leaders in such times. It will also provide students the opportunity to consider how internal bias could affect the organization.