Portraits through the Generations follows a group of biblical figures who have been refashioned in the Second Temple, Mishnah and Talmudic literature. The intriguing question underlying the study is what causes the fluctuations in the nature of the interpretation of their actions, Sometimes a character portrayed in the Bible in a negative light stands in full glory in the later literature, and vice versa: a positive biblical character wrapped in a critique that doubts the purity of her actions. Tracking the nature of the crystallization of traditions on biblical figures opens a wide window to expose hidden stages of development of the creative periods, and allows for a sketch of social, religious, and polemical characteristics that were sometimes disguised in halakhic and legendary genres or presented from one-dimensional perspectives. These exposures allow for a deeper and more complete understanding of the various traditions. In this book, the biblical figures are indeed building blocks, but its main occupation is in deepening the acquaintance with those who chose to write about them and attributing to them motives and deeds that do not adhere to what is described in the verses. The greater the distance between the original character and the character in his new attire, the more it is necessary to understand the motive of the seeker, to know his cultural-social and sometimes even biographical environment. he book is divided into four chapters, which deal with the challenges of Jewish life in the generations from the Second Temple to the Talmudic period: Israel and its foreign neighbors, attribution and greatness in the Torah, leadership, the status of women. In each section, biblical prototypes were chosen that formed the basis for expressing the positions of the homilists in each of the fields. The evaluation of the prototype for positive or negative, the characteristics attributed to it, and the freedom that the homilist took in interpreting his actions differently from what is described in the Bible, are the pieces of information through which the diverse views of the creators of traditions and homilies can be established.