This study connects the dots between the 19th century history of Palestine and modern Arab/Islamic thought by delving into the intellectual history of Palestine during the pivotal 19th century era of Islamic reformism. Despite a wealth of research on modern Arab and Islamic thought in Egypt (e.g., Adams 1933; Gibb 1947; Hourani 1962) and to a lesser extent in other regions such as Syria, Lebanon, and North Africa (e.g., Commins 1990; Sahar 2010), the intellectual history of pre-mandate Palestine has been under-explored. Previous studies on pre-mandate Palestine have primarily focused on its social and cultural history (e.g., Doumani 1995; Tucker 2000). The purpose of this paper is to examine the intellectual history of the renowned al-Khalidi family of Jerusalem. By analyzing five prominent family members, including Ali, Muhammad Ali, Yasin, Yusuf Dia, and Ruhi al-Khalidi, the paper showcases the changes in the family's intellectual and social standing during a time of transformation and modernization. The results indicate that the advent of "intellectual" and "politician" as new categories came at the expense of the traditional roles of qāḍī (judge) and faqīh (jurist). The first two figures, Ali (d. 1816) and Muhammad Ali (d. 1864), embody the intellectual and social conditions of the traditional Ottoman era. They held the prestigious and influential post of deputy qāḍī of Jerusalem, and their social status was derived from their adherence to the traditional system of jurisprudence and the school of law (fiqh). Yasin (d. 1901) and Yusuf Dia (d. 1906), however, signal a shift in the significance of these traditional social roles, which coincided with the political reform of the Ottoman Empire. Yasin first became a qāḍī after completing his traditional education and then was appointed as mayor. Yusuf Dia, Yasin's younger brother, continued this trajectory of change by obtaining modern education in a Protestant school and later serving as the mayor of Jerusalem and a member of the Chamber of Deputies. The final figure, Ruhi al-Khalidi (d. 1913), represents the final stage of the transformation, having received a modern education and being fluent in multiple languages. He held several political posts, including a member of parliament and consul of the Ottoman Empire in Bordeaux, France. Through the examination of these five figures, this paper sheds light on the previously overlooked intellectual history of Palestine in the 19th century