Kautilya was the minister in the Kingdom of Chandragupta Maurya during 317 – 293 B.C. He has been considered as one of the shrewdest ministers of the times and has explained his views on State, War, Social Structures, Diplomacy, Ethics, Politics and Statecraft very clearly in his book called Arthashastra . The Mauryan Empire was larger than the later British India which expanded from the Indian Ocean to Himalayas and upto to Iran in the West. After Alexander left India, this was the most powerful kingdom in India and Kautilya was minister who advised the King. Before Kautilya there were other philosophers in India who composed the Shastras but his work was robust and encompassed all the treaties written earlier. I considered Kautilya for three reasons. Firstly, I wanted to highlight the patterns of thinking in the east which was present long before Machiavelli wrote his “Prince”. Secondly Kautilya’s ideologies on state, statecraft and ethics are very realistic and vastly applicable in today’s context. Thirdly, I feel Kautilya’s work on diplomacy is greatly underrepresented in the western world and it is quite apt to analyze his work in that area. If we compare statesman on the four dimension framework of: War & Peace, Human Rights, International Economic Justice and World Order Kautilya had a strong opinion on all the four aspects. In fact people like Bismark and Woodrow Wilson in recent history had been able to demonstrate their views only on two of the four dimensions. Kautilya’s work is primarily a book of political realism where State is paramount and King shall carry out duties as advised in his book to preserve his state. Kautilya’s work is so deep rooted in realism that he goes to describe the gory and brutal means a King must adopt to be in power. This could have been one reason why Ashoka, the grandson of Chandragupta Maurya whom Kautilya advised renounced violence and war thus taking the path of Dharma or Morals. In this paper, I shall primarily focus on Kautilya’s thoughts on war, diplomacy and ethics. I have devoted a section to compare Kautilya with great philosophers like Plato and later ponder over why Machiavelli’s work looks so abridged and succinct in comparison to Kautilya’s work. Kautilya’s work is then seen in the light of today’s politics and ethics. As Max Weber put it aptly in his lecture, “Politics as a Vocation”, he said Machiavelli’s work was harmless when compared to Kautilya’s Arthashastra.