Generalissimo Chilarai and His Times is the first ever book written in English, on the legendary 16th century hero of many a battle, Yuaraj Suladvaj, most popularly known as Chilarai (the Kite King), the legendary Koch Generalissimo, who held the position of the Commander in Chief and the Dewan (Prime Minister) of Maharaj Naranarayana, the emperor of Kamata-Kamrup (1533 – 87). He is one of greatest warrior heroes and most colourful personalities of all times. In the course of a single military expedition (1562 – 64), he conquered all the kingdoms of the Eastern Region of India, without facing a single defeat. He led a combined Army of 6,00,000 men comprising 5,32,000 land forces and two Naval Divisions, which by aby standard, was a great achievement in itself. Even the great Napoleon commanded an Army of a little more or less the same strength, 250 years later, in 1812, when he invaded Russia, but met with total disaster. It was because of the invincible Chilarai, that during the reign of Naranarayana, neither the Afghans (Pathans) nor the Mughals succeeded in making any inroad into eastern India, beyond the Korotowa. Even the great 17th century warrior hero, Shivaji could not win so many laurels, as Chilarai did. It was Chilarai, who propounded and practiced the tactics of ‘guerilla warfare’ in India for the first time, when he stormed the capital of the Kachari Kingdom, Maibong with a handful of cavalry soldiers, in the dusk hours. Chilarai is also credited as the father of Indian Navy. During the second invasion of the Ahom Kingdom (1562 – 64 A.D), about 60 to 80,000 naval soldiers, under the command of two Admirals, in 1000 bacharis or war boats, joined the combined forces of the generalissimo. This book attempts to focus on the multi-faceted personality of YuvarajSuladvaj alias Chilarai or Sangram Singha.