Women leaders have rarely had the same options open to them as did men, in particular prior to the modern era. In the Jewish world, the tendency to exclude women from the world of learning almost always meant that leadership roles were elusive at best. Nevertheless, every so often, a Jewish woman managed to find a way in which to utilize her talents and to carve out a leadership role for herself. Dona Gracia, Asenath Barazani and Hannah Rachel Verbermacher are three such women. Dona Gracia was born in Portugal in 1510 to a family of wealthy Spanish exiles who were forced to convert in 1497. She married Francisco Mendes, a wealthy converso whose family had also left Spain in 1492 rather than convert. He was a successful businessman who died after the birth of his daughter, leaving behind an infant and a widow. Mendes clearly trusted his wife's abilities and thus named her as guardian of a huge empire, which enabled her to use her talents to chart new paths of action. As a widow, she benefited from the independence that Jewish law grants widows and divorcees. Because she was a shrewd financier with an uncanny ability to plan ahead, she was able not only to become a serious partner in the family business with her brother-in-law in Antwerp, but to continue to run the empire single-handedly after his death in 1543. Dona Gracia was blessed with a fortune and an impressive business savvy, but she also faced serious obstacles as she maneuvered her way from Iberia in search of a home in which she could live openly as a Jew. As she moved from Portugal to England, Antwerp, France, Venice, Ferrara, Ragusa and Constantinople, she displayed an undying altruism and love for the Jewish people while she succeeded in escaping the tentacles of the Inquisition time and again. She not only saved numerous Iberian conversos by organizing escape routes for them, but attempted to boycott the port of Ancona as punishment for the burning at the stake of her follow conversos. She aimed to organize Jewish merchants, shippers and rabbis. She supported yeshivot, publications, synagogues, scholars and hospitals and began to plan an independent settlement in Tiberias (but died in 1569 before moving there). In addition to her generosity, she displayed superb vision, managed an empire, saved most of her property along with conversos from persecution and concocted a brilliant and unparalleled strategy of an economic boycott. The combination of her personal talents with her economic and marital status enabled her to attain a role unmatched by any Jewish male in the 16th century. THERE WERE also women leaders who excelled in the more traditional realm of learning. The scholar has always been revered in the Jewish world, and two women in very different corners of the Jewish world were able to reach the heights of scholarship in the early modern period. Both were born into families which had no sons, a situation that enabled the daughters to "replace" the nonexistent son and achieve a high level of learning. Both became heads of esteemed institutions that, until then, were male dominated and had never experienced a woman leader or would again. Asenath Barazani was the daughter of Rabbi Samuel, an outstanding scholar in 16th-century Kurdistan who had built a yeshiva to improve the rather low level of learning there. He taught her everything he could, and she devoted herself to study. His finest student became his son-in-law and inherited his position as rosh yeshiva, but Asenath was actually running the institution because her husband was so involved in his studies. As a result, she was able to make a smooth transition, and take the male leader's place upon his demise. No one objected to the new head of the yeshiva, because she had already been teaching the students and was so erudite that no one surpassed her. Unlike Dona Gracia, Asenath did not have the luxury of wealth; her father had lived frugally and the yeshiva was dependent upon donors. We have a letter of hers in which she described her predicament in which she had fallen into serious debt; her home and belongings were confiscated. Both father and daughter wrote letters requesting aid from wealthier communities. Nevertheless, Asenath successfully trained many students and was able to send her own son to Baghdad when faced with a request to supply them with a talented scholar. Hannah Rachel Verbermacher of Ludmir faced much stronger opposition than did Asenath, in her case, in a hassidic community in the 19th century. Hannah, also an only child, was extremely learned, and after her father's death inherited his fortune. This enabled her to build a house of study where she observed the commandments, as had her father. Word of her charisma and talents, including her healing ability and learning spread. She dispensed her wisdom while remaining in seclusion, as was common practice among ascetic tzadikim at the time. Men and women, both wealthy and poor, flocked to her court to learn and be blessed or healed. The fact that a woman had taken on a male role was distasteful to some of the male leaders, who claimed that her body was but a vessel for a male soul. Pressure was exerted upon her to marry, a blatant ploy to destroy her status as a holy person. Once she relented to the pressure, it mattered not that her marriage was never consummated; her status had dissipated. She eventually moved to Jerusalem in 1859, where she supposedly had some followers, but died in relative obscurity in 1888. Each of these women carved out for herself an impressive role as a leader. Dona Gracia was single most of her life, and the family fortune enabled her to pursue grandiose and impressive enterprises. Asenath functioned as a scholar in a 17th century male world while married and, as a widow, achieved the ultimate rabbinic leadership position, the head of a yeshiva; her status was based on learning rather than wealth. Lastly, Hannah Rachel lived like a man for part of the 19th century, during which she was visited like any other hassidic tzadik. The world she inhabited had less tolerance for her activities and successfully dethroned her, although her fame lived on. The writer is a professor of Jewish History at the Schechter Institute of Jewish Studies who specializes in Sephardi studies and women's studies.