Shimon Hatsadik was from the remnants of the Men of the Great Assembly...
The previous mishna explained how Prophetic Judaism was, with prophetic sanction, transformed by the Men of the Great Assembly into the forerunner of Rabbinic Judaism as we know it now. The Great Assembly was the transition body that replaced prophetic inspiration, that now ceased, with the ideal of devotion to the Law, ecstatic religiosity with the idea of reflective scholarship, and the ideal of prophetic apprenticeship with group study. We do not know for how long the Great Assembly functioned, one generation or many generations, but Shimon Hatsadik was its last member. Some sources identify him with Iddo ben Yehoshua, the brother of Ezra. If so, Shimon Hatsadik is mentioned in Ezra 3 and the the prophecy of Haggai under that name (Yuchasin). Maor Einaim places him as the 8th generation from Yehoshua ben Yehotsdak (Nechemia 12). His father was Chonio and his son Some say great-grandson) was also called Chonio, the one who built a Temple in Egypt (Menachos 109B). Shimon Hatsadik presented himself in front of Alexander the Great and saved the Jewish people from the machinations of the Samaritans (Yoma 49a). According to Yuchasin, he also instituted the counting of years from Alexander (Minyan Shtoros) and, in the honor of his entry to the Land of Israel, decreed that the year begins in Tishrei, the year previously considered to begin in Nissan . According to Yuchasin, the first schism in Judaism occurred in his time. "When Alexander left Jerusalem, Sanbalt the Horite went out (with him) with a part of Israel as well as some of the sons of Yehoshua the High Priest who have intermarried with Samaritans... Then half the people followed Shimon Hatsaddik and half Sanbalt and his in-laws..."(Yuchasin)
What strikes one about these and other accounts is the perception that Shimon Hatsadik was a transitional figure - between the Men of the Great Assembly that unified Israel and the schisms that have torn it apart subsequently throughout the era of the Second Temple. As a transitional figure, this great leader would be expected to direct the nation towards a program of national existence that sets it upon the path or spiritual prosperity, just like the Men of the Great Assembly did before him. As the undisputed head of the nation, he undoubtedly considered how it should be optimally governed.
Shimon Hatsadik, though the force of his intellect,piety and the prestige of his office held all the power in Judea. He was not only the High Priest but also the President of the Sanhedrin, and Av Beis Din. He also franchised tax collection in Judea (B. Wein, Echoes of Glory, p.37). During the 40 years of his tenure in Judea, its population has grown to 350.000.00 and the population of Jerusalem stood at 120.000.00 (Josephus, Contra Apion 1:197.) It would have been clear to any observer that the main question that stood before the resurgent Jewish polity was: "How and under what principles should it be governed". Was it to be theocratic state, inspired by the ideas of Jewish Scripture, with power diffused among Nasi, as the executive power, the Sanhedrin, as the interpreter of its constitution and the High Priest as the conscience of the state, or would it be modeled after Hellenic political ideas, then sweeping the world. This was the crucial question that divided the Jews then and in the subsequent years.
One can get the sense of how timely this question was from Shimon Hatsadik's contemporary, Ben Sira. It is curious that the last chapters of Ben Sira book are unexpectedly devoted to Enoch, Moses, Aharon, Joshua, Solomon, David, Eliahu, Josiah and finally Shimon Hatsadik. This is totally unexpected for the rest of the book is composed of short maxims, and its conclusion with these personalities is out of character. However, if we take these chapters as a rumination on leadership, they make perfect sense - for the times. It is a reflection on the stature of Shimon Hatsadik that he is listed as the culmination of this august series of leaders.
This is why Shimon Hastadik says three things, paralleling the legacy of the Men of the Great Assembly. Like they, he left guidelines for the future, in his case, guidelines to the leadership that Judea must set up. Unfortunately his advice was disregarded, for had it been followed, perhaps Jewish history would have turned out differently than it ultimately did. What Shimon Hatsadik wanted to see was leadership based on Torah, Temple Service and public welfare. What we got instead was schisms, pursuit of power and betrayal of Jewish tradition.
The problems that confronted Shimon Hatsadik has their parallels at the time of another Shimon - R. Shimon ben Gamliel. How his formula for Jewish survival resembled the prescriptions of Shimon Hatsadik and how it differed is something that we will take up when we get to the last mishna of our chapter.

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