It may be stated at the outset that this essay is essentially an attempt to identify some critical commonalities in the approaches of Sun Zi and Kautilya, the two profound strategists of the ancient Orient, one belonging to China and the other to India, and who exercised considerable influence for centuries that followed in their respective countries. The common view is that Sun Zi was a quintessential military strategist, and Kautilya was a master of the science of politics or Arthasastra What we seek to highlight in this essay is the proposition that both personages had a lot in common and took a holistic view of the affairs of the state.