Introduction The concept of leadership has been discussed and interpreted in the works of world-famous writers thousands of times – the whole of humanity has been always interested in the issues of successful leadership and the ways to obtain these skills. The world history remembers dozens of examples of powerful rulers who remained in the minds and hearts of people as cruel or just, tough or merciful – the succeeding generations study them in their history courses; people consider knowledge about them a sign of intelligence and good education. However, one should never forget that there are a thousand more leaders who failed to impose their will and use their power, were manipulated, conspired, and betrayed. These people are not remembered well as the peculiarity of human nature is to keep in mind only significant things having some impact on individual and social life. In addition, people have been longing to obtain the secret recipe of power that is attractive for everyone – it is essential to be able to reach your goal in life to succeed. Not everyone has this quality, and there has been created no practical guidance to nurture these qualities. Nonetheless, there is much work already done in the sphere that may help both in practice and in theory to analyze the implications of power and ruling. A perfect example of a genuine leader One of the most famous books on the subject of what a genuine leader should be like is Machiavelli’s work “The Prince”. It is a powerful masterpiece of a grand thinker of the Renaissance on the subject of what qualities a leader should possess to be successful, to reign further, and to reach his/her goals. This is a rather provocative piece of writing as it justifies vanity, lies, betrayal, cruelty, and arrogance. This work is often used in the interpretation of the contemporary leadership styles chosen by political leaders all over the world. As it has been noted in the work of Frederick Lewis Schuman (1933) titled “International Politics”, the main essence of Machiavelli’s idea is that “monarchies must be conquered by a superior force” – thus marking out the philosophy of war and tough instruction (36). However, it may also help conduct a literary analysis of another genius work – the one of William Shakespeare titled “Richard II”. The character of King Richard II The present work includes a narrative about two kings, Richard II and Bolingbroke, juxtaposing them and analyzing the peculiarities of their philosophy of power and its influence on their destinies. Richard II loses the war for the throne and is killed by Bolingbroke in the fight for power. It is also significant that Richard II, still being a king, had Bolingbroke in his power but did not use the chance, paying for this failure with his life later. Hence, it is necessary to correlate the actions of both kings from Shakespeare’s drama to the vision of a leader expressed by Machiavelli. The first failure of Richard II was to exile Bolingbroke for such a short period, showing weakness and increasing the threat for his retaining the throne. He showed himself as a merciful leader but doomed himself to death this way (Shakespeare, 1595). According to Machiavelli’s viewpoint