Jabra Nicola (1912 – 1974)—a Trotskyist active in Mandate Palestine and Israel—often emerges in the margins of studies of the Palestinian and Israeli left. He is known as an intellectual who focused on theoretical issues. Nicola began his political life with the Palestine Communist Party (PCP) in 1931 where he became a member of the Central Committee in 1935. He remained within the circles of party leadership until 1943. During this time, he became involved with the Revolutionary Communist League (RCL)—a small Trotskyist group. When the PCP split along Arab and Jewish lines in 1943, Nicola left to work solely with the RCL until the reunification of the party in 1948 as the Communist Party of Israel (CPI). Within the CPI, he was barred from taking on a theoretical role, but led the party’s Arabic literary magazine, al-Jadīd. By 1963, Nicola left the CPI to join Matzpen—a new anti-Stalinist, anti-Zionist party—where he became a theoretical leader. Nicola stands out as a figure with a clear ideological foundation who nonetheless sought out political organizations to disseminate his ideas. I investigate Nicola’s life as a political activist through the history of his involvement in various parties as described by those who knew him. I also consider his writing for The Fourth International, al-Jadīd, and through Matzpen. I argue that, while a formidable intellectual force, Nicola also stands out as a real political leader grounded in ideology. His history of rising into leadership positions in various leftist groups makes him an inside observer over a long period of political turmoil. Rethinking Nicola as a political actor seeking out a place for his ideology not only reveals a new dimension to his own life but helps illustrate the wider leftist political sphere in Mandate Palestine and Israel.