What does it mean to be a family father in a geographically and ideologically dense space such as the Old City of Jerusalem? Here, political oppression co-exists alongside the often precarious economic and social situation of the Palestinian inhabitants; at the same time, commitment to religious, social, and national principles is demanded by local communities, complicating parenting roles considerably. In this paper, I explore the negotiation of these issues within intergenerational familial figurations, based upon participant observation and biographical-narrative interviews with men of various generations in one of the Muslim neighborhoods in the Old City. I show how family fathers experience their parenting role and how they talk about and present questions of what example of a “man” they want to set for their children. Practically, these men experience a strong urge to control their children’s movements tightly (for example, not to encounter settlers or drug addicts), and also their cultural range (not to be exposed to “the enemy’s” cultural products via mobile phones, the Internet, etc.). Family fathers must also negotiate whether to encourage or support their children’s political engagement, for example in acts of resistance, or if they should prevent them from the dangers that come with this. Furthermore, there is a constant and prominent self-reflective discussion within the neighborhood about the low educational aspirations of their offspring, the bad schools in the Old City and the search for alternatives. In my interviews, men frequently contrasted their children’s everyday reality with their own childhood and youth, entering into a self-reflexive process which led to reinterpretations of their past actions and experiences: in reading, for example, the First Intifada as “damaging the Palestinian education for generations”, men were divided between stressing their wish to prevent their children from taking part in overt resistance on the one hand and on the other accusing the current generation as being politically passive. These findings also suggest taking a generational perspective more seriously, e.g. by interviewing members of different generations within a family, or by assessing whether “historical generations” are identifiable in the Old City. However, such an approach needs to take the relevancies of the Old City inhabitants themselves as a starting point and not, as is often done, macro-political issues.