The concept of guerrilla warfare is not decades, but many centuries old, with earliest writing on the subject by Sun Tzu dating back to the 6th Century BC. Some guerrilla tactics are probably as old as the first armed groups of cavemen, being a natural evolution of conflict between groups of disproportionate sizes. One of the earliest examples of guerrilla tactics deployed by a consummate institutional military leader was the Roman general Fabius Maximus who took a course of evade and harassment against Hannibal’s columns. This is a compendium of prominent worldwide guerrilla leaders beginning with William Wallace in the thirteenth century to modern day Sri Lanka. It profiles each leader to analyze their personal history, military tactics, and political strategy. All are home grown leaders in extended guerrilla campaigns many of whom ended up as the first leaders of their countries or liberators of entire regions such as Simon Bolivar. It includes victories and defeats in an effort to tease out not only effective guerrilla tactics but counterinsurgency strategies with some likelihood of success. The advice expounded by Mao Zedong that “the guerrilla must move amongst the people as a fish swims in the sea” with his experiences of long marches over distant countryside regions of China has evolved into a more urbanized context. The name insurgent, freedom fighter, or jihadi is fast replacing guerrilla.