Leadership relates to generation of acceptable and successful solutions and/or outcomes in environments or circumstances that are difficult or seem to have no solutions. If leadership is not in place, there is a feeling of inferiority or intimidation to face and tackle challenges. Although many books have been written in this field, there is still a lot to be done in order to enhance and advance common knowledge of leadership. Many concepts related to leadership theory have been developed through extensive research and others have been borrowed from other branches of study. A good example of a concept applied in the study of leadership is called “the Prisoner’s Dilemma” which is also widely applied in economics (Zaffron 4). This concept lays down tactics and skills that are characteristic of good leadership capable of dealing with complex challenges and intimidating problems. The concept expounds on the reasons of failure and gives ideas on many unexplained scenarios related to the success and/or collapse of business associations in commercial, industrial, private and government organizations. The concept supports the fact that leadership, like many other fields of study, is an entity field and it can be studied as an art or science subject. The theory asserts the qualities of a leader worthy the title of a “good or effective leader”. A good or an effective leader comprehends and plays with tactics of the concept of “the prisoner’s dilemma”. The game is not played once but practiced always in the life of an effective leader and furthermore, the leader should involve others as a team. Among others, the leader has the attributes of: a far-sighted vision; charisma to convince, persuade and envision others to be leaders in their own domains; dedication; faithfulness to all involved at the same level and in both vertical and horizontal set ups of organizations; power of expression and communication; and genuineness. The first two qualities are important in establishing a memorable concept of the prisoner’s dilemma game which always remains live and active in the core of leadership. The other four attributes are applied and their center of attention is on how the game is played in order to effectively attain and achieve good leadership in organizations. Good leadership plays important social roles and can influence many events happening in areas related to politics, family, and commerce. Researchers have conducted many studies on leadership and globally, it is naturally accepted that in order for others to cooperate and play willingly the prisoner’s dilemma game, a method of empowering by delegation, involvement and encouragement from leaders is necessary. Good leaders accept others so that they are accepted too. Good leaders honor others so as to be honored. They respect others and are also respected. Good leaders accommodate glory for all involved. Good leaders are not egocentric. This is the norm for many institutions, societies and organizations. Good leaders have contingent measures that are arsenals to apply in difficult and demanding situations. In order for leadership to work out, commitment is a good strategy and plays an important role. When there are complex problems or decisions to be made, contingent measures are necessary in order to revisit leaders’ communication