Introduction Leadership is important in all organizations and social contexts where people are required to achieve missions, aims, and objectives. It involves influencing, inspiring, and motivating other people to facilitate the achievement of a given goal. Leaders help in planning, managing, directing, and guiding other people towards the attainment of mutual goals. Leadership occurs through the interaction of three major contexts, namely, leaders, followers, and a situation that prompts the deployment of a given leadership strategy. When leading, followers must be involved and hence the reason why there has been substantial scholarly interest in how leaders should associate with their followers to guarantee organizational success. The role of leadership in enhancing organizational outcomes is highly studied in conjunction with various renowned leaders, for instance, Martin Luther King and Winston Churchill, who are regarded as having demonstrated the best headship strategies. Through the comparison of Martin Luther King and Winston Churchill’s leadership styles, this paper evidences that different headship techniques yield different outcomes based on the contexts within which they are applied. Brief Background Martin Luther King Martin Luther King was a key icon in the Negro struggles against racial discrimination. Born in 1929, he was not only a religious leader but also a principal of the civil rights movement that has now redefined the American history, especially in the struggle for the equality of people, despite their race or any other demographic difference. The world remembers him for his nonviolent approaches to transforming racist ideologies that regarded Negroes as inferior to Whites to the extent that they (Negroes) were not allowed to travel by one bus or freely interact in social-environmental settings. In advancing his agenda, Nobel Media (2014) informs that Martin Luther King used tactics such as civil disobedience, which demonstrated his Christianity beliefs concerning nonviolence. Mahatma Gandhi, who is renowned for nonviolent activism, inspired him. Martin Luther King’s effort in the fight against racial discrimination ultimately led to his winning of the famous and celebrated Nobel Peace Prize in 1964. This accomplishment indicated to him and his followers that his efforts and struggles were appreciated to the extent of receiving support from other people who understood the need for ensuring the impartiality of all folks. Indeed, after securing the Nobel Peace Prize, Martin Luther King announced that a significant portion of the cash prize would go into funding his civil right pursuit (Nobel Media, 2014). In 1965, he participated in the organization of Selma Montgomery peaceful protests. Towards the end of his life, he extended his efforts to the fight against poverty and the inversion of Vietnam. He was assassinated in 1968 in Memphis, Tennessee (Steagall, 2015). However, despite the many challenges that he faced, including several arrests, Martin Luther King stood out as a symbolic leader and a key global icon who had marked a new era in American history where contemporary people in the U.S. can now speak freely on issues of discrimination and oppression. Winston Churchill Born in 1874, Winston Churchill was not a great academic p