In the wake of the 2009 dispute over the presidential election in Iran, the regime and the opposition started a tug of war to bring the high rank shi’i clergy or “grand ayatollahs” on their side. Grand ayatollahs responded to the campaign by the opposition and government in three ways, some of them sided with the pro-democracy Green Movement, a few supported the regime, and many of them kept silent. After introducing the organization of the shi’i clergy and a historical background on the interactions between the grand ayatollahs and the Islamic Republic of Iran, this paper investigates different factors influencing different political stances taken by these grand ayatollah in the 2009 episode onward. While the scholarship about religious actors and democratization stress political theology in its explanations, we find that political theology cannot present a satisfactory explanation of the position of the all supporters of the prodemocracy movement in Iran. Instead, this paper argues that the political network of each grand ayatollah was crucial for the position that he took in the 2009 contentious episode. Grand ayatollah who supported the movement either had pro-democratic theology or had ties since 1980s or before to reformists who were leaders of the opposition in 2009. The paper also explains why those who kept silent were outspoken for supporting the pro-democracy movement in Bahrain. Shi’i high rank clergy has been concerned about the domination of Muslims by non-Muslims and Shi’as by Sunnis. Wherever these dichotomies overlapped with democratic struggles of the people they have supported the prodemocracy movements. Besides, whereas some of the grand ayatollahs have been unhappy about the brutal crackdown of the Iranian regime on protestors, they have remained silent because they are afraid their support of the opposition may lead to the collapse of the Islamic government, which has been promoting the shi’i religious practices in Iran.