The Dead Sea Scrolls are Hebrew and Aramaic texts representing more than 800 manuscripts. Found between 1947 - 1956 in 11 caves near an ancient Qumran archaeological site, they consist of copies of books of the Hebrew Bible. The Dead Sea Scrolls have deepened our understanding of the texts of the Hebrew Bible and shed light on the history of late 2nd Temple Judaism (200 BCE to 70 CE). While some scholars believe that the Qumran community produced the Dead Sea Scrolls, others in academia question the accuracy and value of this designation as to what is found in the scrolls because it does not fit so well with the ways the "Essenes" are described in classical sources. The community that wrote the sectarian scrolls had separated from the Jewish priestly establishment in Jerusalem and retreated to the desert to "prepare the Way in the desert" for the end times.By focusing on the earliest and the most recent attempts to date the flourishing of the so-called "Teacher of Righteousness" and his dissenting movement within the historical framework of late Second Temple Judaism in Palestine, we can examine the methods used by the earliest interpreters and contrast them with more recent publications to serve as comparisons that examine this sixty-year period. Although attempts to date the "Teacher’s movement" involves complex and controversial results, the focus is primarily on textual sources from the Second Temple period that provide us with the opportunity to find a potential "fit" between references in the scrolls to the situational context of the "Teacher" and what we know about the history of second and first century BCE parties and politics from other literary sources.