Colonial documents record that War was the natural state of Kerala. They also record that its people were the happiest. Quite incredulous, considering that ever since its discovery, Kerala's political climate was characterized by a variety of Chinese, Arab, European, and local powers fighting each other for economic and military ascendancy. And yet, despite centuries of foreign contact and conflict, it continued to thrive and retain its independence. The frontiers of Kerala were never redrawn and neither did it suffer massive social or cultural dislocations (as in many cases in India and other parts of the world), wherein entire populations and cultures were scattered, subjugated or even wiped out. No foreign orders or influences, especially those inimical to the populace could be imposed until the traditional order, was finally overturned by the end of the twentieth century. The influences Kerala absorbed were of its own choosing. This work attempts to examine and unravel these aspects, draw reasonable inferences and understand their profound influence on society then and residual influences today. It hypothesizes that this remarkable achievement was a direct consequence of Kerala's unique military, diplomatic, social and economic culture. This cultural aspect, along with a deeply interdependent socio-political and economic matrix ensured the well-being of most of Kerala society. A society by no means perfect, but fairly close, causing British administrators, to record that society in Kerala had arrived close to fulfilling the utilitarian dictum of the largest possible happiness of the largest numbers'.