Rabban Gamliel I was succeeded by his son, or as some say, his son-in-law, who took over the spiritual leadership as Nassi during one of the saddest periods of Jewish history. The yoke of the Romans became ever heavier, and oppression made the spiritual and cultural life very difficult. Rabbi Shimon strongly emphasized the importance of religious deeds. Said he: (Avoth I, 17)

"All my life I have been brought up among, the Sages, and I have found nothing better for a person than silence; study is not the most important thing, but practice; and whoever talks too much, brings about sin."

In those days of oppression, many joined the ranks of patriots who wanted to rebel and fight the Romans. Rabbi Shimon supported them very effectively. Even Josephus, the historian, who generally was not his friend, talks very highly about his great knowledge and capabilities. But Rabbi Shimon did not foresee the tragic results of the revolt which ended in the destruction of the Beth-Hamikdosh. He put all his considerable means at the disposal of the war party because he saw no other way out of the desperate situation. In this policy he was not followed by most other Sages who urged peaceful relations with the Romans. In the Mishnah we find Rabbi Shimon's name mentioned in connection with the laws concerning the offering of sacrifices. When poor women, who after childbirth, had to bring an offering, of doves, were embarrassed by the steep price of the birds he pledged that by the next day the birds would be available to them at a much cheaper price. Indeed, he was able to make his pledge come true. Another time Rabbi Shimon is mentioned in connection with the celebration of the Drawing of the Water ("Simchat Beth Hashoeivah"). In the ecstasy of joy, he would juggle torches with great skill. He also was not too proud to personally entertain a groom and bride at their wedding celebration.

Unfortunately, this great scholar and leader was one of the Ten Scholars who died as martyrs at the hands of the cruel Romans. We read the following about his martyrdom:

Rabbi Shimon was thrown into prison together with Rabbi Yishmael ben Elisha, and condemned to die. He cried out in painful sorrow: "Woe to us that we have to be put to death like common heathen and murderers!" When Rabbi Yishmael heard these words, he wondered whether Rabbi Shimon had perhaps once refused to admit a poor and hungry man to his house, while he was sitting at a meal; and that this might be the punishment for it. Thereupon Rabbi Shimon replied: "Heaven knows that I have never in all my life been guilty of this sin. On the contrary, I have always hired people who were on the lookout for beggars in need of food, to bring them into my house." When Rabbi Yishmael questioned him, whether he had felt proud while lecturing to the huge crowd of Jews who had gathered at the Temple mount to hear him expound the Law, Rabbi Shimon replied: "I have never been guilty of such conceit. This punishment is rather a heavenly decree, which no human being can escape."

When both were brought to the place of execution, each one begged to be permitted to die first, so that he would not have to witness the tortures and death of the other. Rabbi Yishmael claimed that, as Kohen Gadol, he was entitled to die first, and Rabbi Shimon argued that being the Nassi gave him the right of being executed first. Lots were drawn, and Rabbi Shimon was executed first. When Rabbi Yishmael saw his head fall into the sand, he picked up the bloody head of his friend, put it in his lap and sobbed: "O sacred, truthful mouth, from which such pearls of wisdom had once flowed! What is it that has caused you to fall into the dust, and your tongue to be sealed off with earth and dirt!" Thus ended the life of one of Israel's noblest princes.