This monograph examines two insurgencies conducted by the Jews in ancient times: The Maccabbee Revolt against the Seleucid Empire from 166-164 BC and the Revolt against the Roman Empire from 66-70 AD. The monograph proposes that all insurgencies have a nature and the nature of insurgency is as critical to understanding an insurgency today as it was two thousand years ago. Ancient Jewish history provides an excellent case study of a successful and failed insurgency. The Jewish revolt against the Seleucid Empire (Maccabbee Revolt 166-164 BC) was a successful insurgency, which gained the free practice of religion for the Jewish people and ultimately an independent Jewish State. This independence lasted for one hundred years until 63 BC when Palestine was annexed by the Roman Empire. Subsequently, the Jewish people again revolted in 66 AD against Roman rule, but the result of the insurgency was a failure catastrophic to the Jewish people and the prospects for an independent Jewish state. The monograph contains four sections: Introduction, Prelude and Nature of Insurgency: The Maccabbee Revolt, Prelude and Nature of Insurgency: The Revolt against Rome, and Conclusion. The model for analysis is the nature of insurgency as defined by US Army Doctrine. The respective natures of each insurgency are each examined separately to provide data for analysis. The data for each insurgency is then compared against the other to determine why one insurgency failed and the other succeeded. The monograph concludes that the differences in the nature of the two insurgencies defined why one succeeded and the other failed. Both insurgencies upon initial examination appear to have a similar characteristics (religious persecution, desire for an independent state, fear of lost cultural identity), but subtle differences in the nature distinguish them. The examination of the Jewish insurgencies in ancient times is relevant to the US military today as it faces insurgencies in Iraq and Afghanistan fueled by strong religious ideologies. The concept of "nature" is still a valuable tool for military planners in the counter-insurgency environment.